Aloha {{first name |}}!

Welcome to the latest edition of the Hawaiʻi Hotel Hui Insider.

This issue has a lot of movement, some of it obvious, some of it hiding in plain sight.

Before we dive in, mahalo to this quarter’s title sponsor, Castle Resorts & Hotels. A long-time local operator that’s stayed focused on what actually matters, people and guest experience. Happy to have them in the Hui.

Maui Seaside is for sale before its expected Tapestry transformation, Castle keeps adding properties, Makeready has apparently been managing The Laylow for a year (man, I am late to the game), and Maui’s vacation rental debate has found yet another sequel.

We also look at Airbnb’s new hotel credit push and what may be the closest thing the company has had to a loyalty program.

And after a few days in New York at NYU and Skift, I came home a little AI’d out, but with a helpful reminder from Danny Meyer: technology changes, hospitality doesn’t.

Know someone in Hawaiʻi hospitality and tourism who should be reading this? Forward it their way. Sharing helps us grow the Hui!

Tired of reading this three days late through your boss's inbox? Join the Hui directly and get the signal sent straight to your own.

Mahalo for coming along for the ride!

Let’s dive in.

Mahalo,

Dan Wacksman
Hawaiʻi Hotel Hui Insider Editor-in-Chief 😄

Pulling the Threads on Tapestry

OK, this one is a little weird.

The 183-room Maui Seaside Hotel has been listed for sale just as it was expected to transition into Hilton's Tapestry Collection. Even stranger, Hilton's website now lists the Tapestry opening date as 2028 rather than this summer.

The timing caught my attention because the current owner, ASAP Holdings, acquired the property in 2022 for $57 million and publicly discussed investing significant capital to take the hotel upmarket. Normally, you execute the renovation, complete the rebrand, and then take the asset to market. Here, the sale appears to be happening somewhere in the middle of the story.

Then there’s how CBRE is marketing the hotel. The property is being offered "fully unencumbered of brand and management." For those who don't spend their days buried in hotel contracts, that means the buyer isn't obligated to keep the Hilton flag, continue the Tapestry conversion, retain Springboard Hospitality, or maintain any existing management arrangement. In other words, the next owner gets a relatively clean slate. Unencumbered is usually a selling point; buyers like the flexibility. What's unusual is seeing it offered that way mid-conversion.

So maybe that's exactly the point. Rather than selling a Tapestry Collection hotel, the owners may be selling flexibility. Either way, this has become one of the more intriguing hotel listings in Hawaiʻi right now.

Read More

Other Hawaiʻi Hotels on the Sales Block

• Oasis Hotel Waikīkī · 96 rooms · Fee simple. Recently secured the leased fee interest. Experienced sellers, so upside may already be priced in.

• Romer House Waikīkī · 179 rooms · Fee simple. Fresh off a major renovation and 47-room expansion. Beautiful product, performance is still catching up.

• Ewa Hotel Waikīkī · 92 rooms · Leasehold · $16.5M.  Reduced below its 2015 sale price of $18.6M. Not something you see every day.

• Paradise Bay Resort: 46 rooms. Fee Simple. Who knew there was a hotel in Kaneohe?  

Hotel Broker info supplied by our friends at Powell & Aucello. 

Castle Keeps Building Its Kingdom

We recently reported that Castle had picked up several new management opportunities, including Waikīkī Circle Hotel, Waikīkī Heritage Hotel, and Bishop Suites at The Executive Centre. Now the company has added another property to its growing portfolio: Lahaina Shores Beach Resort.

The move is particularly meaningful given Lahaina Shores' history. The 199-unit condominium resort suffered significant damage during the 2023 wildfires and only recently completed renovations and a soft reopening. Beginning in July, Castle will assume management of the Association of Apartment Owners (AOAO) and front desk operations.

We discussed this back in February, but here is a quick refresher on how condo resorts/condo hotels usually work. The AOAO runs the building. A front-desk operator, hired by the AOAO, runs the front desk and its own rental pool, often under a brand. Individual owners then decide whether to put their unit in that pool, hand it to a different management company, or just rent it themselves on Airbnb or another platform.

At Lahaina Shores, Castle is taking both the AOAO and the front desk, and it plans to pull more owners into its rental pool. That last part is the whole game. You can't yield-manage rooms you don't control.

Full disclosure: Castle is a proud sponsor of the Hui. Since sponsoring, they've added four new properties. Coincidence? 😉 

And if you're interested in new management contracts sponsoring and supporting the Hui, please feel free to reach out anytime.

Read More

Stop Gifting Your Guests "Island-Scented" Chemicals
-Sponsored-

Let’s be real: guests know the difference between a generic lotion made on the continent and the real thing. If you’re still stocking vanity kits filled with synthetic fragrances, you’re missing a chance to anchor your brand in true place-based luxury.

Based in Waimea, Ua Hawaiʻi has spent 30 years perfecting clean, vegan skincare powered by native ingredients like kukui oil and botanical infusions.

These aren’t just "amenities", they are high-performance products that reflect your property’s quality. They already grace the counters of Hawaiʻi’s top-tier resorts because they deliver actual authenticity. It’s time to ditch the "aloha-wash" and give guests something they’ll actually want to take home.

Wait... Who's Managing The Laylow?

In each issue, we try to feature interesting jobs. When a Managing Director position for Makeready crossed my desk recently, my first reaction wasn't "what a great job." It was "wait... who's Makeready?"

After doing a little digging, I learned that Makeready took over management of The Laylow in May 2025, replacing Pyramid Global Hospitality. Man, I am late to the game. Based on Pyramid's website, Wayfinder Waikīkī appears to be its only remaining managed property in Hawaiʻi. I think I need to create a management company scorecard! Who’s on first? 

Makeready and The Laylow share the same parent company, Rockbridge, a Columbus-based hospitality investment firm that owns the hotel. Makeready is Rockbridge's in-house lifestyle brand and management company, a collection of independent hotels that deliberately stays in the background. According to an industry source, the decision was largely about keeping operations streamlined and under one roof. In other words, why hire an outside manager when you have one of your own?

What's even more notable is that The Laylow is Makeready's first managed property in Hawaiʻi. Whether it's the beginning of a broader expansion into the Islands or simply an internal ownership decision remains to be seen.

Either way, it serves as a reminder that management contracts change hands all the time, often with little fanfare. Sometimes the biggest hospitality news isn't the deal that gets announced. It's the one you realize happened a year ago.

Which is my long way of saying: we hear a lot at HHH, but clearly not everything. If you've got some tea for us, loop us in.

Bill 9’s Escape Hatch?

As we've covered in previous issues, Maui's vacation rental saga refuses to end. Quick recap: Bill 9, now law, phases out more than 6,000 apartment-zoned short-term rentals over the next several years, on the premise that those units should return to the long-term housing market.

Back in February, all three county planning commissions (Maui, Lānaʻi, Molokaʻi) rejected the carve-out that would have spared about 4,500 of them by creating two new hotel zoning categories, H-3 and H-4, for properties that operate more like visitor lodging than housing. That looked like the end of it.

It wasn't. In late May, the proposal, now Bill 88, cleared the County Council committee 6-1, the exact supermajority it needs to overcome the commission's unanimous denial. Chair Alice Lee and Vice Chair Yuki Lei Sugimura, two of the three who voted against Bill 9, are now backing the carve-out, and they warned about exactly this. Both argued the H-3/H-4 zoning should have existed before Bill 9 ever passed, with Sugimura calling the current sequence "chaos." But Bill 9 passed 5-3 over their objections. Now the county is bolting on the zoning that its own dissenters said should have come first.

And the courts are already in it: within days of Bill 9's signing, Kāʻanapali owners sued, calling the phase-out unconstitutional.

As we’ve said before, like much legislation, the intent is good. The execution is a mess.

Read More

Airbnb Finally Finds Loyalty?

We previously talked about Airbnb going all in on hotels, and last month, Airbnb announced an interesting move: guests who book select hotels can receive up to 15% back in Airbnb credit, along with a price match guarantee if they find a lower rate elsewhere.

The credit expires after one year and can be used toward future Airbnb stays, experiences, and services. In other words, Airbnb may have created the closest thing it has ever had to a loyalty program.

Naturally, I had to test drive the hotel path, or lack thereof.

When I searched Oʻahu, Airbnb served up a promotion pop-up offering 15% back on featured hotels, with a button to click for hotel search. Searching New York showed hotels mixed directly into the results alongside vacation rentals. Searching Maui and Los Angeles? Nothing. No hotel prompt, no obvious hotel path, and very little indication that hotels were part of the experience at all.

My guess is that inventory (not enough of it) may be part of the issue, but after playing around with a few destinations, I couldn't quite figure out the strategy. It feels like Airbnb is testing multiple approaches at once. Sometimes hotels are front and center. Sometimes they're hiding behind a pop-up. Sometimes they barely appear.

For a company trying to become a meaningful hotel distribution channel, the experience still feels surprisingly confusing. Airbnb may have figured out the rewards program before it figured out hotel search.

Give Guests a Taste of Hawaiʻi That Gives Back
-Sponsored-

Every hotel and business gives gifts. Why not choose one that directly supports Hawaiʻi’s local community?

Whether you’re welcoming VIPs, recognizing valued clients, or creating memorable guest experiences, Baker’s Heart offers locally made gifts that do more than delight. As an employment social enterprise of nonprofit Touch A Heart, our cookies provide meaningful job training for individuals working to overcome homelessness, addiction, justice involvement, and other barriers to success.

Baked in Honolulu with ingredients like kiawe pod and ʻulu flour, each purchase offers a special taste of Hawaiʻi. Perfect for welcome amenities, client gifts, meetings, conferences, or special events. Custom gifts, branded products, and specialty orders are also available.

Share purpose, aloha, and the spirit of Hawaiʻi with every gift.

Notes From New York: AI, Hospitality, and a Little Perspective

I spent some time in New York recently, attending both the NYU Hospitality Investment Forum and the Skift Data + AI Summit, and thought I'd share a few observations.

After two conferences where nearly every conversation somehow found its way back to AI, I have a confession:

I'm a little AI'd out.

The energy reminded me of previous technology waves. The internet was going to change everything. Then big data. Then cloud. Then blockchain. The pattern is familiar. The technology is real, the impact is real, but the timeline is usually longer than the conference speakers would have you believe.

One moment stuck with me.

During the Skift conference, a room full of travel executives and technology leaders was asked who had seen meaningful ROI from their AI investments. Very few hands went up.

I don't know whether those who raised their hands actually measured it, and nobody was exactly fact-checking the responses, but it did make me pause. For all the excitement, urgency, and investment flowing into AI, the room wasn't exactly overflowing with proven success stories.

That's not a criticism of AI. It just suggests we're still early.

My takeaway was simple: pick one or two areas where AI can genuinely move the needle for you or your business, experiment aggressively, and ignore the noise.

Ironically, my favorite session had almost nothing to do with technology.

Hospitality legend Danny Meyer (Union Square Cafe, Shake Shack, 11 Madison Park) sat down with another industry giant, Jonathan Tisch (Loews Hotels and longtime New York tourism leader), for a conversation about leadership, hospitality, and why the fundamentals still matter. 

One idea stuck with me: hospitality isn't just an industry, it's a business principle. Whether you're running a restaurant, hotel, airline, bank, or tech company, people remember how you made them feel.

He also talked about his upcoming book, What Could Possibly Go Right? The phrase came from the early days of Shake Shack, when a simple hot dog cart in Madison Square Park turned into something much bigger. His point wasn't to ignore risk. It was that too many people start with all the reasons something won't work instead of asking what might happen if it does.

That whole conversation struck a chord, because it was almost the opposite of the AI chatter happening everywhere else. While everyone was focused on what technology might do someday, Meyer was talking about taking smart risks, creating great experiences, and betting on people.

In a week dominated by talk about algorithms, automation, and artificial intelligence, that may have been the most valuable lesson of all.

The technology keeps changing. Hospitality doesn't.

Stretched Teams. Messy Systems. Stalled Projects. We Fix That.
-Sponsored-

Hotel teams know what needs to get done, but limited resources, disconnected systems, and competing priorities can slow down even the most important projects.

Sassato helps hotel and travel companies move critical projects forward, from PMS, CRS, CMS, and booking engine decisions to RFPs, vendor selection, system health checks, contract support, training, and project management.

We step in when teams are stretched, technology feels messy, timelines are slipping, or big decisions need outside perspective.

With decades of experience across hotel operations, marketing, revenue, technology, and finance, we help teams cut through complexity, make smarter decisions, and get the right work across the finish line.

Industry Events

• The 6th Annual Hawai‘i Hotel & Restaurant Show - June 17-18th, 2026 (Oahu)

• Maui WaiWise Stewardship Summit - Nov 9-10, 2026 (Maui)

  • Free educational forum hosted by Maui County DWS focused on hotel water conservation, sustainability, and operational efficiency

Full list of 2026 Hawaiʻi Events 

*If you have industry events to share, please email me at Dan@hawaiihotelhui.com.

Spotlight on Hawai‘i Hospitality Opportunities

• Managing Director - Makeready (Honolulu)

• Market Vice President, Hawaii - Marriott International (Honolulu)

• Vice President Sales, The Americas - OUTRIGGER Hospitality Group (Honolulu)

• Hotel Director of Sales & Marketing - Grand Naniloa Hotel Hilo - DoubleTree by Hilton (Hilo)

*If you happen to have any job openings, let us know. We will be glad to include them in the newsletter, space permitting; send the job link to Dan@hawaiihotelhui.com.

It’s funny how an inbox works. Some weeks you get a slow trickle of polite nods, and other weeks it feels like someone kicked a hornet’s nest of highly opinionated hospitality executives.

Let's see what’s keeping everyone talking this week.

Keep the Kudos Coming!

• "You crack me up. Love the headline."

• "SO love this newsletter."

• "I’m always so impressed with the clear, concise, informative, and thorough communication. Truly impressive job from you and your team, my friend! Bravo!"

• "Congrats! I always love receiving the newsletter!"

• "Excellent brief."

• "As someone who handles all our month-end reports, I just wanted to say—the Market Performance Report is incredibly clean and clear. It really stands out. For context, I used to spend a lot of time scrolling through the DBEDT and HTA websites to track down the relevant data. Your report essentially eliminates that step, which is a real time-saver."

  • By the way, you can still download the monthly report here.

The HTA CEO Salary Search

• "GOOD ON YA! for stating the craziness of the HTA CEO job search! That salary is ridiculous for the HTA CEO."

  • HHH Note: It remains one of the great paradoxes of local tourism governance. Expecting a world-class executive to steer a multi-billion-dollar economic engine while offering a salary that wouldn't cover a mid-tier resort GM is a bold strategy.

Reimagining Hilo (The Banyan Drive Reset)

• "So true! Let’s hope some very good planning and decision-making by local leaders can transform Hilo into its quiet beauty and help spur sustainable economic growth."

  • HHH Note: Hilo has a distinct soul you simply cannot replicate. Tearing down the former Country Club Condominium Hotel is the easy part. The harder, more intriguing puzzle is what happens next.

Rose-Colored Proformas (And Debt Hazards)

• "Leverage is good as long as you can manage your debt load. Not owing money to a bank opens many opportunities for the operator and also takes away stress."

• "Being too leveraged is a house of cards in many cases. Especially when you count on low wages, low interest, low expenses, and increasing ADR to make the deal work. Stress-test your proforma and put away the rose-colored glasses. That is just prudent."

  • HHH Note: Very wise words that too few actually follow in practice. It's incredibly easy to get addicted to cheap debt and leverage, pulling cash out of a current deal just to fund the next one. When the market is roaring, it makes you look like a financial genius. But when the wind shifts... that house of cards folds incredibly fast.

Agree? Disagree? The Inbox Remains Open!

What’s making you lose sleep, roll your eyes, or celebrate on the property floor this week? The inbox is open for your anonymous confessionals, spicy takes, or sharp industry critiques. Fire back over at dan@hawaiihotelhui.com or dan@sassato.com and tell us where we got it right, or where we missed the mark entirely.

About Us

Hawaiʻi Hotel Hui was started by hotel industry veteran Dan Wacksman, CEO of Sassato, a Hawaiʻi-based consultancy that combines deep local expertise with a global perspective.

Our team brings decades of experience across operations, marketing, revenue, tech, and finance, all aimed at helping hotels and travel companies make smarter decisions and move faster. Whether you need additional expertise, extra horsepower, or just someone who thinks like you and moves things forward, we’ve got you. From local independents to global brands, we show up with a no-nonsense, results-focused mindset. To be blunt: we get sh*t done.

Recent projects include brand transitions, system selection (PMS, CRS, CMS — all the acronym soup), implementations, project management, feasibility studies, training, audits, and everything in between.

A lot of organizations deal with stretched teams, siloed processes, and messy tech stacks that quietly stall important work. We fix that. Happy to chat if this hits close to home.

Aloha {{first name |}}!

Welcome to the latest edition of the Hawaiʻi Hotel Hui Insider.

This issue seems to have accidentally turned into a newsletter about change. Before we dive in, mahalo to this quarter’s title sponsor, Castle Resorts & Hotels. A long-time local operator that’s stayed focused on what actually matters, people and guest experience. Happy to have them in the Hui.

HTA is looking for a new CEO, Banyan Drive is preparing for another attempt at reinvention, Paradise Cove is making way for a very different version of Ko Olina, Google wants AI to become your travel agent, and hotels across the country are wrestling with the rising cost of labor, insurance, taxes, and just about everything else.

I recently spent some time back in my hometown of New York City for meetings and conferences, wandering through old neighborhoods that barely resemble the city I grew up in. Places evolve whether we're ready for it or not. The challenge isn't stopping change. It's making sure we don't lose what made a place special in the first place.

And if you missed it last month, we launched a new downloadable monthly report, published on the first Tuesday of each month, that summarizes key hotel data with actionable context. We'd love to hear what you think. Should we keep it going? 

Know someone in Hawaiʻi hospitality who should be reading this? Forward it their way. Sharing helps us grow the Hui!

Tired of reading this three days late through your boss's inbox? Join the Hui directly and get the signal sent straight to your own.

Mahalo for coming along for the ride!

Let’s dive in.

Mahalo,

Dan Wacksman
Hawaiʻi Hotel Hui Insider Editor-in-Chief 😄

Wanted: Tourism Expert, Cultural Diplomat, Political Punching Bag. Big Job, Modest Pay.

Fresh off the Senate’s approval of the new HTA Advisory Board, an HTA press release popped into my inbox announcing the official search for a new Hawai‘i Tourism Authority president and CEO.

I had actually thought the search was ongoing, but this seems to suggest otherwise. According to the release, the new leader will help guide Hawai‘i tourism into a “new era” while balancing economic priorities, community concerns, cultural values, destination stewardship, marketing, and oversight of the Hawai‘i Convention Center. Easy peasy. 😉

What caught my attention was the wording. The release repeatedly emphasizes collaboration with DBEDT, government, and the newly reshaped advisory board, a reminder that HTA today looks very different from the more independent authority it once was. The new CEO will operate under significantly more political oversight and scrutiny than many of their predecessors.

And then there’s the salary. Following last year’s very public debate around HTA leadership compensation, the position is now capped at the Lieutenant Governor’s salary (Act 168), currently around $185K annually. For what may be one of the most politically exposed and publicly dissected executive roles in the entire state, that’s probably going to narrow down the candidate pool pretty quickly. Not a terrible salary by most standards, but when recent hotel GM/MD postings in Hawaiʻi have ranged from roughly $150K to $500K, it does put things into perspective. 

You’ll need tourism expertise, political patience, crisis management skills, and the ability to survive Hawaiʻi’s endless tourism culture wars while everyone simultaneously blames tourism for everything, while also depending on it for the economy. No pressure.

Interested in applying? 😁 Deadline to Apply is June 26th.

Job Description

Banyan Drive’s Latest Redevelopment Plan: Demolition First, Vision Later.

The state appears ready to move forward with demolishing the former Country Club Condominium Hotel on Hilo’s Banyan Drive, with lawmakers backing roughly $14M–$15M for demolition, grading, and site work.

The six-story property has been vacant since early 2025, after redevelopment talks stalled and Banyan Drive Management walked away from its proposed long-term lease deal. Since then, the site has mostly become an expensive security headache, with the state paying to keep it from becoming another Uncle Billy’s-style squatter and fire problem.

But this also appears to signal a bigger pivot: future development on Banyan Drive may move inland because of sea-level rise concerns, leaving some shoreline parcels as open space instead of rebuilding directly on the water.

Lawmakers are also discussing the possible acquisition of the Grand Naniloa Golf Course as part of the broader redevelopment puzzle. That seems to make a lot of sense. Too much land planning in Hawaiʻi happens parcel by parcel, with no larger vision until the damage is already done.

The bigger developers have figured this out. Look at Howard Hughes and Kakaʻako: whether you love every tower or not, Ward Village shows the power of having a coordinated, long-term plan instead of a haphazard approach.

If Banyan Drive is truly going to be reimagined, Hilo needs that same kind of bigger-picture thinking, just with a version that actually fits Hilo.

Demolition may finally clear away the physical blight. The harder question is whether Hilo has a real master plan waiting on the other side.

Read More
Hawaiʻi Legislature / SB3288 text

Stop Gifting Your Guests "Island-Scented" Chemicals
-Sponsored-

Let’s be real: guests know the difference between a generic lotion made on the continent and the real thing. If you’re still stocking vanity kits filled with synthetic fragrances, you’re missing a chance to anchor your brand in true place-based luxury.

Based in Waimea, Ua Hawaiʻi has spent 30 years perfecting clean, vegan skincare powered by native ingredients like kukui oil and botanical infusions.

These aren’t just "amenities", they are high-performance products that reflect your property’s quality. They already grace the counters of Hawaiʻi’s top-tier resorts because they deliver actual authenticity. It’s time to ditch the "aloha-wash" and give guests something they’ll actually want to take home.

The Price of Paradise (Cove) and Progress

Back in January, we mentioned the closure of Paradise Cove, and last week, I was surprised to come across a Washington Post feature story on the iconic Ko Olina Luau. The story framed Paradise Cove as a victim of the tourism ecosystem it helped create: Ko Olina grew into a luxury powerhouse, land values exploded, and eventually a massive middle-market luau stopped penciling out.

I came across the article as I was back in my hometown of New York City for meetings and conferences, walking through old neighborhoods that barely resemble the city I grew up in. Some changes are better. Some are worse. Either way, the city I knew is very different.

Reading about Paradise Cove, I felt that same mix of nostalgia, sadness, and reluctant acceptance. Places evolve. Consumer tastes change. Economics change. What once made perfect sense can eventually become impossible to sustain.

Editor-in-Chief Dan and family. 25 years later and still a cherished memory! A good reminder that sometimes the overpriced souvenir photo is worth every penny. 😂

The Paradise Cove site is now slated for a $135M redevelopment with retail, restaurants, entertainment space, and a smaller luau component. In other words: less mass-market tourism, more upscale mixed-use “experience economy.”

It is hard not to see the broader trend. We have talked many times about the desire to attract “higher-spending visitors.” Well, this is what that strategy starts looking like on the ground: fewer large-scale middle-market attractions, more luxury positioning, higher land values, higher operating costs, and pricier experiences.

Hawaiʻi’s cost of living is brutal. Employees need higher pay to survive. Owners want stronger returns on increasingly expensive assets. Guests are already pushing back on rising prices, fees, and shrinking value. That three-legged stool is wobbling again. More on that below.

Paradise Cove will not be the last example. Progress always has a cost. The hard part is admitting that some of the places we’re nostalgic for were already changing long before we were ready to let them go.

Read More

Disney Elevates Kimberly Agas at Aulani

Congrats to Kimberly Leimomi Agas, who has been promoted from General Manager of Aulani to Executive Director, expanding her role into broader strategic and community leadership initiatives.

Kim has been part of Aulani since day one, joining the opening team 15 years ago and serving as GM for the past decade. I’ve had the chance to work with her over the years, and she is clearly a great fit for the role: calm under pressure, deeply respected, and someone who genuinely understands both hospitality and Hawaiʻi (and Disney Magic 🐭).

Congrats, Kim — wishing you much success in this next chapter!

The Coconut Wireless Is Never Wrong

In the last issue, we reported that the coconut wireless was buzzing: Thomas Foti was leaving his role at Marriott and taking the helm as Managing Director of Hilton Hawaiian Village.

Well, it became official last week, with multiple stories covering the move and Thomas updating his LinkedIn page. We still couldn’t find the actual Hilton press release, but it's close enough. 😉

When we started this newsletter, we didn’t exactly expect to be breaking news. But here we are — our first scoop.

Congratulations, Tom. Based on the comments we heard from so many people on LinkedIn, you are clearly well respected, and Hilton Hawaiian Village is lucky to have you stepping into such a huge role.

Hotel Performance

Quick Summary (So You Sound Smart in Meetings): Statewide is RevPAR up ~2.6%, but all on the strength of the neighbor islands. Oʻahu is hitting a rough patch (RevPAR down ~4.8%), Maui is dominating as the rate leader at $544+ with RevPAR surging ~10.9%, and the Big Island and Kauaʻi hold strong with RevPAR up ~9.2% and ~2.9%.

HTA and DBEDT publish a lot of great data. We curated the metrics that actually matter to hotel operators, added context, and packaged it into a monthly report. If it's useful, we'll make it a regular thing.

Click here to sound REALLY smart in your next meeting: HHH Market Performance Report.

*Hotel performance data will be published in the first issue of each month.

Expedia’s Annual Pep Rally

Expedia held its annual Explore conference a few weeks ago. When I was on the hotel side, I always viewed these events as a bit of an Expedia pep rally, polished presentations, partnership buzzwords, and enough corporate enthusiasm to make you quickly refill your drink.

I did not attend this year, but I got my hands on the Cleveland Research Recap and, buried beneath the corporate theater, found a few interesting takeaways.

Probably no surprise, but Expedia believes the future of travel booking belongs to (wait for it….) AI agents, not humans, doom-scrolling hotel listings.

The company is leaning heavily into AI trip planning, natural language search, and connected booking assistants. One line that stood out was: “Content Quality is Match Quality.”

Translation: if your hotel content is outdated, incomplete, or sloppy, the AI may simply stop recommending you. This has always mattered, but now it is on steroids.

A few other interesting nuggets:

• Business travelers now make up 35% of Hotels.com demand and convert at roughly 3x the rate of leisure travelers.

• Expedia is still pushing packages hard because bundled bookings generate higher value and repeat rates.

• Expedia’s ad business hit $758 million, which clearly shows many hotels are paying for position and paying commission. Add the two, and you will be surprised by what the actual cost of the booking is. (As an aside, Booking Holdings just launched BKNG Ads, giving partners one ad team across Booking.com, Priceline, and Agoda -- showing they want a piece of this lucrative pie as well.)

For hotels, the math keeps getting messier: commission, media spend, sponsored placement, package discounts, loyalty promos… at some point, “OTA production” needs its own fully loaded P&L.

Whether the guest starts on Expedia, Booking, Google, ChatGPT, or some AI travel agent we haven’t heard of yet, the rule is the same: clean content, strong economics, and knowing exactly what you’re paying for.

Read More

Stretched Teams. Messy Systems. Stalled Projects. We Fix That.
-Sponsored-

Hotel teams know what needs to get done, but limited resources, disconnected systems, and competing priorities can slow down even the most important projects.

Sassato helps hotel and travel companies move critical projects forward, from PMS, CRS, CMS, and booking engine decisions to RFPs, vendor selection, system health checks, contract support, training, and project management.

We step in when teams are stretched, technology feels messy, timelines are slipping, or big decisions need outside perspective.

With decades of experience across hotel operations, marketing, revenue, technology, and finance, we help teams cut through complexity, make smarter decisions, and get the right work across the finish line.

Hospitality’s Three-Legged Stool Is Getting Wobbly

The hotel business has always rested on a three-legged stool: staff, guests, and owners. The problem is everyone wants more from the same dollar now, and the math is starting to crack.

This past week brought another wave of labor headlines that could reshape hotel economics for years to come. In Los Angeles, city leaders are debating whether to delay the so-called “Olympic Wage” ordinance, which would push hotel workers’ minimum wages to $30/hour by 2028. Meanwhile, in New York, unionized hotel workers just ratified a massive new eight-year contract that could push some top housekeeper wages above $60/hour by 2034 in one of the country’s most expensive labor markets.

In Hawaiʻi, the recent Local 5 contracts in Waikīkī reportedly raised average housekeeper wages from roughly $28/hour to nearly $38/hour over four years, establishing a new benchmark for union hotel labor in the Islands.

And really, workers have a point. Housing, food, healthcare, and transportation costs have exploded everywhere, but Hawaiʻi may be one of the hardest places in the country to make the math work. Many hotel employees still can’t realistically afford to live anywhere near the resorts they work in.

But owners aren’t exactly innocent bystanders here either. Over the past decade, plenty of hotel assets were aggressively leveraged, refinanced, or acquired at valuations that assumed endless ADR growth and cheap debt forever. That worked great when money was basically free. Today? Interest costs, labor, insurance, taxes, and renovation expenses are all climbing at once.

So what happens? The guest gets squeezed: higher rates, more fees, leaner staffing, and fewer services, all while being sold a “luxury experience.”

Rising wages, higher taxes, insurance pressure, softening international demand, and debt-heavy ownership structures all seem to be hitting at once.

The reality is the industry needs balance. Staff deserve wages that reflect actual living costs. Guests deserve value and service levels that justify what they’re paying. Owners deserve returns, too, but not every aggressively financed deal deserves to be rescued through endless rate hikes and fee creep.

Eventually, guests push back. And when they do, everybody feels it.

New York Wages, Los Angeles Wages

Google Wants to Be Your Travel Agent

Google I/O is Google's version of Apple's Worldwide Developers Conference, except somehow geekier. Held in late May, it's not exactly appointment viewing for hotel operators. But this year, buried in the AI announcements, Google made something pretty clear for travel: it does not just want to help people search for hotels. It wants to help them book.

The big shift is that Google Search is becoming more agentic. Instead of just typing "best hotels in Tokyo" and getting links, travelers may soon ask Google's AI to compare options, check rates, monitor prices, recommend the best fit, and eventually complete the booking.

A few things worth watching:

• Google is expanding its Universal Commerce Protocol (UCP) into lodging, which could allow AI agents to move from hotel search to actual booking.

• Google's Agent Payments Protocol is being built so AI agents can transact on a user's behalf, with guardrails like budget limits and brand preferences.

• AI Mode and AI Overviews are making search more conversational, meaning travelers may ask longer, more specific questions instead of typing short keywords.

• Google's AI Max -- a new campaign type that replaces traditional keyword targeting -- is bringing travel ads into these AI-powered search experiences, shifting from keyword matching toward intent matching.

• Early partners mentioned around these efforts include major travel players like Amadeus, Booking.com, Expedia, Hilton, Marriott, and Trip.com.

Translation: Google is rebuilding both the top of the funnel and the bottom of the booking path at the same time.

For hotels, this is not just an SEO story anymore. It is search, metasearch, content, booking engine, payments, advertising, and distribution, all starting to blur together.

If your content is outdated, your Google Business Profile is weak, your rates are inconsistent, your room descriptions are vague, or your booking path is clunky, the AI may simply recommend someone else (see Expedia story above).

And on the paid side, there is a tradeoff coming. AI Max may help hotels show up in more conversational, trip-planning searches, but it also means giving Google more control over which queries trigger your ads, what gets shown, and where the user lands.

For years, hotels optimized for humans typing keywords into Google. Now we may need to optimize for Google's AI deciding which hotels humans should even see.

Industry Events

• The 6th Annual Hawai‘i Hotel & Restaurant Show - June 17-18th, 2026 (Oahu)

• Maui WaiWise Stewardship Summit - Nov 9-10, 2026 (Maui)

  • Free educational forum hosted by Maui County DWS focused on hotel water conservation, sustainability, and operational efficiency

Full list of 2026 Hawaiʻi Events 

*If you have industry events to share, please email me at Dan@hawaiihotelhui.com.

Spotlight on Hawai‘i Hospitality Opportunities

• General Manager - The Walt Disney Company (Kapolei)

• Director of Marketing & Public Relations - Fairmont Kea Lani - Maui (Wailea-Makena)

• Director Sales and Marketing - OUTRIGGER Hospitality Group (Kailua-Kona)

• Market Vice President, Hawai’i - Marriott International (Honolulu)

• Sales National Account Director - Prince Resorts Hawaii (Honolulu)

*If you happen to have any job openings, let us know. We will be glad to include them in the newsletter, space permitting; send the job link to Dan@hawaiihotelhui.com.

The inbox was relatively quiet this week, well that is compared to previous weeks! Maybe you were all out enjoying the beach, or maybe just avoiding your screen time (though our 72% open rate in the last issue would beg to differ 😉).

While the volume was low, the takes remained sharp! Though the amount of praise we've been getting lately is dangerously close to getting to our heads. To prevent a massive ego trip, please keep sending in your thoughts, and feel free to send some hate mail or tell me where I'm completely wrong, just to keep me grounded.

Here is what's on the mind of the Hui this week.

Keep the Kudos Coming!

• “You crack me up. Love the headline.

• “SO love this newsletter.” “

• “I’m always so impressed with the clear, concise, informative, and thorough communication. Truly impressive job from you and your team, my friend! Bravo!”

The Tech & Travel Disconnect

• “Most people on a trip open a ride-share app after they arrive at the destination airport. Some will reserve a ride in advance... I am not convinced that consumers will change their use and book the hotel first and then the ride, food delivery etc. Maybe subscribers will do that as long as the platform is buying the business, but that is not a sustainable business model. In real life, my plumber is not the first one who comes to mind when I need my shower tiled, the lights fixed, or the roof replaced.”

  • HHH Note: This is an excellent reality check. Tech platforms love to pitch the ultimate "all-in-one super app" dream, but consumer habits are incredibly stubborn. Breaking down those silos in travel is a lot harder than it looks on a pitch deck.

• Google loosened the rules because it forces small hotels to spend money on their trademark. Interesting that there is no OTA bidding on the "Hilton Hawaiian Village" keyword, and you do not see Pepsi advertising on the "Coca Cola" search

The STR Pendulum (The Short-Term Rental Shift)

• “Do Short-Term Rental Platforms grow the overall visitor numbers for a destination? In most places, probably not, and they will just shift business from other OTAs. In Hawaiʻi, it could be a little different as the STR business is seeing major political headwinds and inventory is shrinking. These platforms may potentially expose hotels to guests who would have otherwise picked a short-term rental.”

  • HHH Note: Most historical stats show that the short-term rental business actually did grow the total tourism pie in Hawaiʻi over the last decade, much to the chagrin of those who believe our annual visitor numbers should max out strictly based on available hotel rooms.

• “IMHO, Airbnb has lost tremendous share on Oʻahu. Savvy hotels will pulse the market continuously and compete with rates when it makes sense… I am excited to watch how this goes.”

  • HHH Note: They certainly have. If you look at the recent data, short-term rental occupancy is running significantly lower than hotels, even after stricter county regulations have reduced total STR inventory. The pendulum swung incredibly far in the vacation rental direction for years, but through a mix of heavy regulation and shifting customer preferences, it's swinging back. Eventually, the market will find its natural equilibrium.

The Airport Soundcheck (Re: AI Music at the airport))

• “Shame! For a destination which demands authenticity, this is an embarrassment...

• “A terrible idea! Who thought of this blunder and who approved it?? 🤦‍♂️.

Agree? Disagree? The Inbox Remains Open!

The inbox is open for your anonymous confessionals, spicy takes, or sharp industry critiques. Fire back over at dan@hawaiihotelhui.com or dan@sassato.com and tell me where we got it right, or where we missed the mark entirely.

About Us

Hawaiʻi Hotel Hui was started by hotel industry veteran Dan Wacksman, CEO of Sassato, a Hawaiʻi-based consultancy that combines deep local expertise with a global perspective.

Our team brings decades of experience across operations, marketing, revenue, tech, and finance, all aimed at helping hotels and travel companies make smarter decisions and move faster. Whether you need additional expertise, extra horsepower, or just someone who thinks like you and moves things forward, we’ve got you. From local independents to global brands, we show up with a no-nonsense, results-focused mindset. To be blunt: we get sh*t done.

Recent projects include brand transitions, system selection (PMS, CRS, CMS — all the acronym soup), implementations, project management, feasibility studies, training, audits, and everything in between.

A lot of organizations deal with stretched teams, siloed processes, and messy tech stacks that quietly stall important work. We fix that. Happy to chat if this hits close to home.

Aloha {{first name |}}!

Welcome to the latest edition of the Hawaiʻi Hotel Hui Insider.

The 2026 legislative session just wrapped, Mufi Hannemann is stepping down from HLTA after more than a decade, and Hyatt just opened two hotels in 'Ewa Beach, or is it one hotel?

Before we dive in, mahalo to this quarter’s title sponsor, Castle Resorts & Hotels. A long-time local operator that’s stayed focused on what actually matters, people and guest experience. Happy to have them in the Hui.

Here's what we're covering this issue: the HLTA leadership transition and what it means for the organization's future, a full legislative scorecard on the bills that made it and the ones that didn't, a new GM on the Kohala Coast and maybe one at Hilton Hawaiian Village, and what Google's latest moves mean for hotel marketing and distribution.

Know someone in Hawaiʻi hospitality who should be reading this? Forward it their way. Sharing helps us grow the Hui!

Tired of reading this three days late through your boss's inbox? Join the Hui directly and get the signal sent straight to your own.

Mahalo for coming along for the ride!

Let’s dive in.

Mahalo,

Dan Wacksman
Hawaiʻi Hotel Hui Insider Editor-in-Chief 😄

Hyatt Doubles Up in West Oʻahu

Hyatt is officially opening the dual-branded Hyatt Place Ho‘opili and Hyatt House Ho‘opili in ‘Ewa Beach on May 19th, bringing 240 rooms to one of Oʻahu’s fastest-growing residential areas.

If you’ve ever wondered why hotel companies love these combo projects, it’s pretty simple: two brands, one building, shared back-of-house, and the ability to capture multiple traveler types at once.

Hyatt Place targets the shorter-stay business and leisure crowd, while Hyatt House leans into extended-stay guests with kitchens and apartment-style setups. Same building, different customers. The new property(s) are managed by PM Hotels, who now manage 4 properties on Oʻahu (or is that 3, does this count as one or two??). Alaka’i Development owns the property.

At first glance, it may seem like a strange place for a hotel, but we are betting on strong occupancy from military, government, business, and visiting friends and family.

Mufi Exits to Polite Applause… and Quiet Sighs of Relief

Mufi Hannemann announced he’s retiring from the Hawaiʻi Lodging and Tourism Association (HLTA) after more than a decade leading the organization.

Supporters point to successes such as the Charity Walk, scholarship initiatives, and workforce development during his tenure. Critics, however, have been far less sentimental, arguing that HLTA became increasingly politicized under his leadership, drifted from its core role of hotel advocacy and member support, and created such a deep rift with AHLA that the Hawaiʻi Hotel Alliance was eventually formed, in part, to give hotels a stronger direct advocacy voice alongside AHLA.

His later entanglement in the ongoing HTA board drama, including his resignation as chair following controversy over the state audit and convention center usage issues (see past HHH issue), only reinforced the perception that HTA had become increasingly dysfunctional.

His departure also raises a bigger question: what exactly should HLTA be going forward? An advocacy organization? A workforce and community-focused nonprofit? Both? And the next CEO, assuming there is one, inherits an organization facing some existential questions.

For those playing at home and drowning in Hawaiʻi tourism acronyms:

• HLTA: Hawaiʻi Lodging and Tourism Association (see above)

• HHA: Hawaiʻi Hotel Alliance, a newer hotel-focused advocacy group aligned with AHLA

• HVCB: Hawaiʻi Visitors and Convention Bureau, contracted by HTA to market Hawai’i

• HTA: Hawaiʻi Tourism Authority, the state agency overseeing tourism strategy, contracts, and destination management (Part of DBEDT)

• HTA Board: The governor-appointed volunteer advisory board

Stop Gifting Your Guests "Island-Scented" Chemicals
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Let’s be real: guests know the difference between a generic lotion made on the continent and the real thing. If you’re still stocking vanity kits filled with synthetic fragrances, you’re missing a chance to anchor your brand in true place-based luxury.

Based in Waimea, Ua Hawaiʻi has spent 30 years perfecting clean, vegan skincare powered by native ingredients like kukui oil and botanical infusions.

These aren’t just "amenities", they are high-performance products that reflect your property’s quality. They already grace the counters of Hawaiʻi’s top-tier resorts because they deliver actual authenticity. It’s time to ditch the "aloha-wash" and give guests something they’ll actually want to take home.

Speed Lawmaking, Hawaiʻi Style: Final Scorecard

Back in March, we flagged several hospitality-related bills moving through Hawaiʻi's frantic 60-day legislative sprint. The sprint is over. Here's what survived, what didn't, and what it means.

A reminder that Governor Green still has until July to sign, veto, or simply let bills become law without his signature.

• Dedicated Tourism Marketing Funding (HB 1950): Dead.

  • The effort to create stable, dedicated tourism marketing funding didn’t survive conference season.

  • Translation: Hawaiʻi tourism marketing remains tied to annual budget fights and political priorities.

• State Budget / HTA Funding (HB 1800): Mostly survived.

  • While dedicated funding failed, lawmakers largely preserved HTA and DBEDT tourism allocations through the budget process.

  • The 67.75 million includes marketing, destination stewardship, workforce programs, and Waikīkī beach funding.

  • The true marketing budget is $39.6 million, well below many of our competitor destinations.

• $25 Comp Room Fee (SB 241): Dead.

  • Hotels dodged this one. The proposal would have added a fee on complimentary rooms 🤷‍♂️.

• Vacation Rental Enforcement (HB 1590): Dead.

  • Good intentions, poorly written, and ultimately died after industry groups warned the amended language could unintentionally shield illegal vacation rentals, potentially creating more harm than good.

• HTA / Destination Management Restructure (ultimately SB 1571): Passed.

  • HTA survives, but weaker. The board becomes largely advisory, while more authority shifts toward the Governor and DBEDT. Depending on who you ask, this is either long-overdue accountability or the slow dismantling of Hawaiʻi’s independent tourism agency.

  • On that note, the Senate confirmed all 11 members of HTA's newly restructured advisory board in April. Two come directly from the hotel industry: Kim Agas of Aulani and Danny Ojiri of Outrigger. The board retains one meaningful responsibility worth watching: recommending candidates for the HTA CEO position. Which brings us to the uncomfortable reminder that it has now been nearly three years since John De Fries stepped down. Three years!

• Michelin Guide Support (SB 2072): Dead. 

  • Still one of the stranger debates of the session. Nothing inspires confidence quite like hearing testimony supporting a bill from people who didn’t seem to fully understand how the business model works.

And our final fun at the legislature, Green Fee Sleight of Hand

When the Green Fee was first introduced, the pitch was fairly straightforward: raise the TAT by 0.75 percentage points and create a dedicated funding source for environmental issues, guided in part by an advisory council assembled by the Governor.

We warned at the time that the structure felt eerily familiar to the original transient accommodations tax (TAT), which was initially created as a dedicated tourism marketing fund before gradually becoming part of the general fund. And now the Legislature is already heavily reshaping the Green Fee process. Lawmakers replaced or modified roughly 40% of the council’s original project recommendations during budget negotiations, inserting their own priorities while cutting or reducing several of the council’s recommended initiatives.

That doesn’t necessarily mean the projects are bad. But it does reinforce a concern many in the industry raised early on: whether the Green Fee would remain dedicated or gradually become another flexible pool of state spending funded by visitors.

Read More

Leadership Shuffle at Waikīkī’s Biggest Hotels?

A recent Marriott job posting caught our attention: Dual General Manager for both the Moana Surfrider and Sheraton Princess Kaiulani.

Wait… wasn’t that Thomas Foti’s role?

Industry sources tell us Foti has recently resigned and may be headed for an even bigger opportunity on Oʻahu. And there may be no bigger hotel role open right now than Managing Director for Hilton Hawaiian Village, which has been without a permanent leader since Debi Bishop’s departure.

Nothing official has been announced yet, but in Hawaiʻi hospitality circles, vacancies at the top rarely stay quiet for long, nor does the coconut wireless.

Fairmont Orchid Names Todd Temperly as General Manager

Fairmont Orchid has appointed Todd Temperly as General Manager of the 540-room Kohala Coast resort.

Temperly most recently led The Ritz-Carlton, Cleveland, which, no offense to Cleveland, is about as far from the Kohala Coast vibe as you can get. Thankfully, he’s no stranger to Hawaiʻi, having previously served as Resort Manager at Grand Wailea. His résumé also includes leadership roles at Waldorf Astoria Chicago, Conrad Chicago, and the iconic Palmer House Hilton.

Aloha and Good Luck Todd!

Uber + Expedia: The Super App Chase Continues

Uber officially entered the hotel booking business through a new partnership with Expedia, allowing users to book hotels directly inside the Uber app. On the surface, it looks like another distribution partnership. Underneath, it looks a lot more like the early stages of something bigger.

For years, rumors have floated around about Uber potentially acquiring Expedia, especially given that Uber CEO Dara Khosrowshahi previously ran Expedia as CEO for more than a decade. Nothing materialized, but this partnership feels like a logical halfway step: combine Uber’s massive daily user base with Expedia’s global travel infrastructure and slowly train consumers to stay inside one ecosystem.

The bigger ambition here may not be hotels at all. It may be the long-discussed “super app” model popularized by platforms like WeChat in China, where transportation, travel, dining, payments, delivery, messaging, and commerce all live inside a single app experience. Uber already has rides, food delivery, grocery, and memberships. Expedia adds flights, hotels, and broader travel inventory. Throw in a digital wallet and loyalty ecosystem, and suddenly the pieces start looking very super appy.

The real question is whether Western consumers actually want a super app. Silicon Valley has been chasing the idea for years. So far, nobody has fully cracked it.

Read More

Drive Direct Bookings from Hawaii.com
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Hawaii.com puts your property in front of high-intent visitors while they’re building itineraries, planning experiences, and learning about the islands, helping you stay top of mind before OTAs win the booking.

If you want more qualified visibility and a smarter path to direct bookings, we can help.

Airbnb Continues Its March Into the Hotel Business

A few months ago, we mentioned Airbnb’s growing hotel ambitions after the company made several key hotel industry hires, including dedicated market managers focused on signing hotel inventory. We even have one here in Hawai’i. Now we’re getting a clearer picture of where this may be heading.

Airbnb CEO Brian Chesky recently described the traditional OTA model of separating hotels and vacation rentals into different tabs, or awkwardly mixing them in search results, as “pre-AI thinking.” Instead, Airbnb appears to be moving toward a more personalized approach where the platform decides what type of accommodation to show based on traveler behavior and booking history.

That’s a shift from Airbnb’s earlier hotel experiments, which often felt clunky and bolted onto a platform originally built for home sharing. This feels more well-thought-out and potentially more competitive for traditional OTAs. The company is already actively working with hotels on Oʻahu. And like most new OTA entrants, they have lower commission rates to prime the pump. But rest assured, this will not last long. 😉

Google Now Knows Which Bed You Want

Some people think Google wants to steal your booking. That’s not quite right, and the reality is actually more nuanced.

Google is not trying to become Booking.com. At least not yet. When a traveler books through an AI-generated Google recommendation, the reservation still flows through to an OTA, a brand site, or a metasearch partner. Google doesn’t take the room night. What Google takes is the toll.

And it just built a lot more toll booths.

On April 17th, Google upgraded its hotel price tracking from city-level trends to individual property alerts. Travelers can now follow your specific hotel, monitor rates for exact travel dates, and receive alerts the moment prices change.

It also launched Canvas, an AI trip planner that builds itineraries directly inside Google using real-time hotel and flight data. And it introduced AI Max for Travel, which places hotel ads directly inside AI-generated responses while shifting more control over placement and messaging away from hotel marketers and toward Google’s AI.

Every one of these tools follows the same logic: keep the traveler inside Google’s ecosystem longer, capture more of the planning journey, and extract a toll at every stage before the booking ever reaches you.

The piece many hotels are missing is that this is not really a distribution play. It’s an infrastructure play. Google doesn’t necessarily want to be your competitor. It wants to be the road everyone else has to drive on: OTAs, brand sites, metasearch, and eventually AI travel agents too.

And if you want your property visible to a traveler planning a trip inside Google’s AI Mode, you’re probably paying for that visibility one way or another.

The real question worth asking your digital marketing team: are you showing up inside AI Overviews and AI Mode, or are you invisible before the traveler ever even reaches a booking page?

And Google isn’t alone. As we mentioned earlier, Uber just added hotel booking through Expedia. The tollbooth economy is expanding fast. Or as my good friend Tim Peter likes to say: Gatekeepers Gonna Gate.

Want to dive deeper? Google Blog, April 17, 2026

Industry Events

Your Next Guest Isn’t Googling You: How to Win Bookings in the Age of AI

Join HSMAI Hawaiʻi and Hawaiʻi Hotel Hui for a free practical session on how AI is changing hotel discovery, with clear strategies to increase visibility, capture demand earlier, and drive more direct bookings.

• Your Next Guest Isn’t Googling You: How to Win Bookings in the Age of AI  - May 20, 2026 (Webinar)

• The 6th Annual Hawai‘i Hotel & Restaurant Show - June 17-18th, 2026 (Oahu)

• Maui WaiWise Stewardship Summit - Nov 9-10, 2026 (Maui)

  • Free educational forum hosted by Maui County DWS focused on hotel water conservation, sustainability, and operational efficiency

Full list of 2026 Hawaiʻi Events 

*If you have industry events to share, please email me at Dan@hawaiihotelhui.com.

Spotlight on Hawai‘i Hospitality Opportunities

• Catering Sales Manager - CLÜME (Honolulu)

• Market Vice President, Hawai’i - Marriott International (Honolulu)

• Director of Rooms - Four Seasons Maui (Maui)

• Director of Revenue Management - Hale Hokuala Kauai, Curio Collection by Hilton (Lihue)

• General Manager - Grand Wailea, A Waldorf Astoria Resort (Wailea)

• Sales National Account Director - Prince Resorts Hawaii (Honolulu)

*If you happen to have any job openings, let us know. We will be glad to include them in the newsletter, space permitting; send the job link to Dan@hawaiihotelhui.com.

The inbox was absolutely smoking this week. Between the macro-economic reality checks, the frustration over losing major events, and a solid dose of unverified development gossip, you all definitely had a lot on your minds.

Let’s dive into what you had to say this month.

The Fuel That Keeps Us Going

• “Love this, Dan!! It sounds great! (The HHH Theme Song)”

• “Your writing is great - keep up the great work! I share the data points with my directors and clients and the little snarks about being an ‘aspiring marvel villain’ with my team so we can all enjoy :)”

• “I wanted to say that your March 2026 Industry Intelligence Report has been extremely helpful for a number of our clients... These days, we have so much data coming at us that it is hard to decipher it all into digestible pieces to share with owners and boards. You are spot on with your reporting.”

  • Note: If you have not seen the report, you can check it out here.

• “Just want to say I'm absolutely impressed by the content here. Great work!”

Fading Spotlights & The Event Exodus

• “This is a tough but important wake‑up call for all of us in Hawaiʻi’s visitor industry. The loss of [a major sporting event] isn’t just a sports story. It’s a signal of how fragile our economic ecosystem has become. When major events start walking away, it forces us to confront the reality that rising operational costs, regulatory uncertainty, and a shifting political climate are making it harder for hoteliers and tourism partners to compete on a global stage. Hawaiʻi has always been a premium destination, but even premium destinations need a stable, collaborative environment.”

• “Not only are sporting events leaving. How many TV series are left after [the iconic island police dramas] were pulled as well? These series brought Hawaiʻi into the homes of millions of people every week - and they were shown on a global scale. The islands are starting to lose their share of awareness. In 20-30 years, most people who are fit enough to travel won't have a concept of Hawaiʻi any longer. Only local residents and older tourists will have the visual experience and memories.”

The Cost, Culture, and "AI Slop" Collision

• “Shame! For a destination that demands authenticity, this is an embarrassment.”

  • Regarding the state Department of Transportation officially playing 'AI slop' at HNL.

• “There are a plethora of factors at play: The mass media perpetuated the ‘stay away from our islands’ aspect of the pandemic! The continued rhetoric of no visitors/tourists on the islands. The [disaster] response from government agencies is confusing to locals and visitors alike. The cost of a family of four visiting from [the West Coast] to spend 5 nights on Maui is about $12K!!! The cost of gas and groceries is beyond grossly unjustified... Let’s not forget the homeless people who are everywhere! And then to see a visitor disrespect a Hawaiian monk seal and act as though it’s an arbitrary act... leading again to residents not wanting those types of people here on the islands, but shown as not wanting ANY tourists.”

• “Many destinations are currently pursuing a strategy to attract 'high-quality' or 'luxury' tourists as they are experiencing push-back from their local population due to tourism's impact on traffic, resources, cost of living, pollution, etc.”

Boardrooms and Billionaire Retreats

• “The Mandarin developers’ MO was to acquire property on an option basis if possible so as not to expend capital, put a package together to sell to an investor or developer, get the entitlements, and then sell, leaving the development and sales risks to the new owner. When he got involved with this property, I thought he would do the same thing – and he did. “

• “To be honest, I think the elites who don't reside in Hawaiʻi, [tech billionaires and media moguls] and the many others who fly private under the radar, are perfectly fine with this and see it as a long-term desired plan to create their own world retreat…”

Have a hot take, a wild industry theory, or a reason why I'm entirely wrong? The inbox is always open for your anonymous confessionals.

Send your thoughts to dan@hawaiihotelhui.com or dan@sassato.com, and you might just see your words here in the next edition.

About Us

Hawaiʻi Hotel Hui was started by hotel industry veteran Dan Wacksman, CEO of Sassato, a Hawaiʻi-based consultancy that combines deep local expertise with a global perspective.

Our team brings decades of experience across operations, marketing, revenue, tech, and finance, all aimed at helping hotels and travel companies make smarter decisions and move faster. Whether you need additional expertise, extra horsepower, or just someone who thinks like you and moves things forward, we’ve got you. From local independents to global brands, we show up with a no-nonsense, results-focused mindset. To be blunt: we get sh*t done.

Recent projects include brand transitions, system selection (PMS, CRS, CMS — all the acronym soup), implementations, project management, feasibility studies, training, audits, and everything in between.

A lot of organizations deal with stretched teams, siloed processes, and messy tech stacks that quietly stall important work. We fix that. Happy to chat if this hits close to home.

Aloha {{first name |}}!

Welcome to the latest edition of the Hawaiʻi Hotel Hui Insider.

Things have been eventful since the last issue. We had the Travel Weekly conference and all the events that surround it, and we hit a 68.79% open rate, which is essentially unheard of. I think it means people actually like us! Well, maybe not everyone, as I had my first run-in with someone who was not thrilled with one of our stories.

For the record, I’m not trying to upset anyone. But I’m also not going to water things down just to keep everyone comfortable. A big part of why this newsletter works is the POV. If it turns into safe, recycled PR, we might as well pack it up now.

From day one, the goal has been to build a real community, not just a distribution list. That means conversations, disagreements, and the occasional uncomfortable moment. I’m well aware not all my takes are right (just ask my wife, she’ll confirm).

So if you agree, disagree, or think I’ve completely missed the mark, let me know. You can jump in publicly on LinkedIn or send me a note directly. If it’s good (or brutal enough), it might make its way into the Anonymous Comments section.

Before we dive in, mahalo to this quarter’s title sponsor, Castle Resorts & Hotels. A long-time local operator that’s stayed focused on what actually matters, people and guest experience. Happy to have them in the Hui.

In this issue, we kick off with the latest hotel development headlines, big vision, familiar names, and a healthy dose of “let’s see what actually happens.” From there, we break down a 25-year golf tradition, calling it quits, and what Hawaiian Airlines’ shift onto Alaska’s systems really means behind the scenes. And yes, we’re side-eyeing the decision to pipe AI-generated “island vibes” through the airport instead of, you know… actual Hawaiʻi music. And yes, curiosity got the best of us, so we made our own HHH AI theme song. Read on for the link to listen (it is so bad it is good!).

Good intel is too heavy to carry alone. Lighten the load and forward this to a colleague who needs a reality check.

Tired of reading this three days late through your boss's inbox? Join the Hui directly and get the signal sent straight to your own.

Mahalo for coming along for the ride!

Let’s dive in.

Mahalo,

Dan Wacksman
Hawaiʻi Hotel Hui Insider Editor-in-Chief 😄

Nothing Says Luxury Like a Mall Parking Lot

Last issue we called it out, many in the industry want to position Hawaiʻi as a luxury destination… but the product doesn’t always back it up. As we mentioned, only about 18% of the state’s hotel inventory actually falls into the luxury category.

Now, a couple of heavy hitters seem to be stepping up to (small kine) fill that gap. Larry Ellison, Oracle co-founder, 98% owner of Lānaʻi, newly minted media mogul and aspiring Marvel villain, is looking to expand Sensei Lānaʻi. The additions will include “several” luxury villas and spa facilities, clearly aimed at the ultra-high-end wellness traveler. Meanwhile, the Kobayashi Group is pushing a new 38-story luxury hotel and residential tower at Ala Moana designed for well-heeled guests. On paper, this is exactly what the market needs. In reality? We’re still talking about a handful of villas on Lānaʻi and a hotel being dropped into a mall parking lot.

Yes, Park Lane worked, I know… people love it. I still don’t quite get the appeal of “luxury living” in a mall, but clearly the market disagrees.

In a somewhat related note, a recent LinkedIn post by CoStar’s Jan Freitag showed that, among major U.S. markets, Oʻahu has the oldest hotel inventory, with roughly 80% being over 20 years old and less than 2% of new rooms under construction relative to that base. So any new or renovated inventory is a big deal.

Still no word on the Mandarin Oriental down the street from the proposed Kobayashi project. I put on my reporter’s cap and tried calling the number on the website… out of service. Not exactly a great sign. If anyone in the Hui has the real story, I’m all ears. But my bet, based on conversations with some folks in the know, is that this project is all but dead.

For now, being a true luxury destination still feels a bit aspirational.

Ala Moana Project, Lanai Project

Hold My Beer

The Travel Weekly Hawaiʻi Leadership Forum is pushing 30 years, and at this point, it's less a conference and more an industry ritual. Sold out, familiar faces, and friends texting me asking if I had connections to snag a ticket. You'd think Bruno Mars was playing.

Credit where it's due: Justin and the Travel Weekly team put on a well-organized, smoothly run event. And the food at the Sheraton was excellent, if not a bit over the top!  Now, about the agenda...

The format will feel familiar if you've been before. Lots of updates; HTA, Airlines, OTAs, and the always amusing wholesale panel. Some sessions were basic updates with a few interesting data points being shared. But two moments stood out.

Aaron Salā at HVCB was again the most compelling voice in the room. He's one of the few people in this space who genuinely understands both sides of the equation: the economic importance of tourism to the state and the responsibility to balance it with the community and culture that make Hawaiʻi worth visiting in the first place. Clear, consistent, and worth hearing every time. 

And Ray Snisky put the current moment in perspective in a way that stuck. Paraphrasing: we've been through 9/11, the financial crisis, COVID... "hold my beer." We'll be okay. Hard to argue with that.

The most substantive conversation came from the wholesale panel, and the message was direct: competitive destinations are outmarketing us. They're spending more, telling better stories, and winning travelers who would have defaulted to Hawaiʻi five years ago. We're not losing on product. We're losing on presence. The window to fix that is open right now, but it won't stay open forever.

The irony is not lost on us that the same week, HB1950, which would have given HTA more stable marketing funding, was killed in the legislature. 🤷‍♂️

Like most events like this, the most honest exchanges happened on the sidelines, away from the mic. Which is great... but also kind of the point. If the real conversation is happening in the hallway, maybe that's where the agenda should be.

That's something we're thinking about here at the Hui. More on that soon.

Stop Gifting Your Guests "Island-Scented" Chemicals
-Sponsored-

Let’s be real: guests know the difference between a generic lotion made on the continent and the real thing. If you’re still stocking vanity kits filled with synthetic fragrances, you’re missing a chance to anchor your brand in true place-based luxury.

Based in Waimea, Ua Hawaiʻi has spent 30 years perfecting clean, vegan skincare powered by native ingredients like kukui oil and botanical infusions.

These aren’t just "amenities", they are high-performance products that reflect your property’s quality. They already grace the counters of Hawaiʻi’s top-tier resorts because they deliver actual authenticity. It’s time to ditch the "aloha-wash" and give guests something they’ll actually want to take home.

The Sentry Is Gone. The Math Won.

We flagged this earlier in the year when The Sentry was “temporarily” moved off Maui. Now it’s official: after 25+ years, the PGA Tour is done at Kapalua.

This was a ~$48M direct economic driver for Maui, and now the Sony Open in Kahala could be downgraded to a Champions event. Fewer top players, less attention. We once had 13 televised events. Now we’re down to three, and maybe soon zero.

What we don’t talk about enough is the exposure. These tournaments deliver hours of global broadcast, the kind of marketing Hawaiʻi would pay millions for. That’s disappearing too.

From what we’re hearing, the state wasn’t really part of the conversation. We don’t know if Hawaiʻi was asked to sweeten the pot, but even if it was, it’s hard to imagine us competing on cost.

Moving crews, equipment, and production to Hawaiʻi isn’t cheap; this feels like a spreadsheet decision.

The course was the excuse. The margins made the decision.

Hard to stay on the global stage when the stage starts moving somewhere else.

Same Tail. Different Airline?

The “HA” code story already made the rounds, so we’ll skip the nostalgia. The more important shift just happened: Hawaiian is now fully running on Alaska’s passenger service system. That’s the backbone, reservations, check-in, app, everything.

At the same time, Hawaiian officially joined the oneworld alliance, expanding connectivity to nearly 1,000 destinations globally. At the Travel Weekly conference, Hawaiian Airlines CEO Diana Birkett Rakow painted a compelling picture of oneworld access, stronger tech, and a more generous loyalty program. Hard to argue with any of that.

But can the personality and culture of the airline survive when the guts are all Alaska?

It kind of reminds me of the OTA playbook. When Expedia acquired Travelocity (and Orbitz), it replaced everything, but the logos and some design to Expedia’s systems, and the brands slowly faded. On the flip side, Booking acquired Agoda and let them run independently on their own platform, and it flourished. Not saying that’s what happens here, but we’ve seen how this story can play out.

The Pualani tail still flies for now, but the operation behind it is now firmly Alaska’s.

Hotel Performance

Quick Summary (So You Sound Smart in Meetings): Statewide performance is basically flat, RevPAR up just ~0.6%. Oʻahu is softening (RevPAR down ~2.2%), Maui is still the rate leader at $530+ but slipping, and the Big Island and Kauaʻi are quietly doing the heavy lifting with RevPAR up ~9.6% and ~6.7%.

HTA and DBEDT put out a ton of valuable data. We went through it and pulled out the areas we feel are most relevant to hotel folks, and added a bit of narrative to help the numbers make sense. If it’s useful, we’ll make it a regular thing.

Click here to sound REALLY smart in your next meeting: HHH Market Performance Report.

*Hotel performance data will be published in the first issue of each month.

Amex: The New Booking Channel

Cleveland Research recently flagged a pretty telling data point from Amex: lodging spend through Fine Hotels & Resorts (FHR) was up 50% YoY in both Q4 and Q1, roughly 10x faster than overall lodging growth on their network.

The program expanded with about 300 new properties added. But that doesn’t explain all of it. High-value travelers seem to be consolidating into platforms that bundle perks, points, and a smoother booking experience.

And they’re willing to pay for it. FHR rates can run meaningfully higher than booking direct, which means guests are actively choosing the platform and the perks over the lowest rates. A lesson for revenue managers?

Also worth noting: the average age of a new U.S. Platinum cardholder is now 33. That’s a long runway for Amex to own that relationship. It seems some guests aren’t starting with your brand. They’re starting with Amex (or Chase or Capital One…).

One interesting point that came up at the Travel Weekly conference, not every “luxury” traveler is high net worth. Many are stretching to get there, using credit or buy now, pay later options (BNPL) to access the experience. Instagram has us all chasing billionaire travel experiences on beer budgets.

Makes you wonder if there’s a takeaway here for mid-scale. The demand for the experience is there. The question is how it’s being packaged and who’s capturing it.

Quick Note: What is FHR? Fine Hotels & Resorts (FHR) is Amex’s hotel program for certain cardholders. Hotels have to be selected/approved to be part of this network. It bundles perks like free breakfast, property credits, upgrades, and late checkout. Chase recently launched a similar program called The Edit.

Drive Direct Bookings from Hawaii.com
-Sponsored-

Hawaii.com reaches visitors while they’re choosing islands, building itineraries, and deciding where to stay.

We help hotels show up at that critical moment through ads, sponsored articles, itinerary placements, and native recommendations. Instead of competing on price, you influence the decision early, when travelers are still forming preferences.

If you want more qualified visibility and a smarter path to direct bookings, we can help.

AI Aloha

The state Department of Transportation is playing AI-generated, “island-themed” songs on rotation at HNL, one per hour, from 5 a.m. to midnight. No state funds were used, we're told. A clever intern and a free Suno subscription, we’re guessing.

Hawaiʻi has one of the most distinctive musical traditions on the planet. A rich scene of local artists who would, by all accounts, love the exposure. But the state landed on a different solution: an AI tool that generates lyrics like "from the baggage crew to the TSA line, everything's fine." 

To be fair, the traditional playlist still runs the rest of every hour, licensed from real artists. The AI songs were added on top of that, at no additional cost, which does raise the question of what exactly we're optimizing for here. The answer appears to be: synthetic, vaguely Jawaiian vibes.

Every hotel in Hawaiʻi is selling authenticity. The culture, the sense of place, the feeling that you couldn't get this anywhere else... that is the product. HNL is the front door. And right now, the front door is playing AI slop. Listen and decide for yourself.

And of course, we couldn’t help ourselves, listen to our HHH AI Original tune “Local Voice, No Delay” (it is so bad it is good). I wonder if we can get Henry Kapono to record it! 😉😉

Read More

When CEOs Start Playing Defense

A LinkedIn post from a Cloudbeds PMS CEO, Adam Harris, calling out Mews for running Google ads under the “Cloudbeds” keywords quickly turned into one of the more active industry threads we’ve seen in a while. It didn’t stop there. Another PMS CEO, Stayntouch’s Jacob Messina,  jumped into the comments, turning it into a very public back-and-forth that felt less like marketing chatter and more like competitive positioning playing out in real time.

The reactions were split. Some saw it as standard performance marketing, others called it deceptive. An agency eventually stepped in to take responsibility, which is rare enough to be notable on its own.

Fun fact, and one that might make some of you cringe… You can bid on a competitor’s brand terms, even if they’re trademarked. Google loosened the rules years ago and largely pushed enforcement onto the trademark owner. Translation: the auction is wide open.

Now, before everyone calls their lawyer, a quick reality check. You generally can’t stop someone from bidding on your name. That’s fair game. Where it crosses the line is if they try to pretend to be you in the ad copy or mislead the guest into thinking they’re the official site. That’s where you have some recourse.

If this sounds familiar, it should. OTAs have been doing this to hotels for years, bidding on your brand, showing up above you, and inserting themselves right at the moment of booking.

Different category, same game. And like it or not, if you’re not defending your brand in search… someone else probably is.

Industry Events

Your Next Guest Isn’t Googling You: How to Win Bookings in the Age of AI

Join HSMAI Hawaiʻi and Hawaiʻi Hotel Hui for a free practical session on how AI is changing hotel discovery, with clear strategies to increase visibility, capture demand earlier, and drive more direct bookings.

Date: Wednesday, May 20th, 2026 Location: Prince Waikiki Time: 11:00 AM-12:00 PM HST

• Visitor Industry Charity Walk - May 9, 2026 (Maui)

• Your Next Guest Isn’t Googling You: How to Win Bookings in the Age of AI  - May 20, 2026 (Webinar)

• The 6th Annual Hawai‘i Hotel & Restaurant Show - June 17-18th, 2026 (Oahu)

• Maui WaiWise Stewardship Summit - Nov 9-10, 2026 (Maui)

Full list of 2026 Hawaiʻi Events 

*If you have industry events to share, please email me at Dan@hawaiihotelhui.com.

Spotlight on Hawai‘i Hospitality Opportunities

• Market Manager - Priceline (Hawai’i - Remote)

• General Manager - Grand Wailea, A Waldorf Astoria Resort (Wailea)

• Assistant Marketing Manager, Pre-Arrival - Hilton Grand Vacations (Honolulu)

• Guest Services Manager - OEM - Highgate (Honolulu)

• Learning & Development Manager - Mauna Lani, Auberge Collection (Waimea)

*If you happen to have any job openings, let us know. We will be glad to include them in the newsletter, space permitting; send the job link to Dan@hawaiihotelhui.com.

Judging by the heat in my inbox this week, the "Hui" has plenty on its mind. Let’s get into this week’s "Industry Therapy."

The "Warm & Fuzzies" (Praise)

• "Your newsletter is one of the most informative and actually useful emails I get. Helps me to keep up to date with the industry in under 10 minutes."

• "It’s your authentic self reflected in a world where nearly everything we hear is touched by AI. Keep up the great work."

• "Kudos to Hawaii Hotel Hui! You’re doing a fantastic service for us!"

• "I can’t tell you how much intel, joy, and relevance your newsletter has brought to my attention after a 45-year career that started right where you are, Waikiki! Thank you for bringing nostalgia right to my fingertips!"

The Luxury Gap & The Cost of "Premium"

• "Your perspective about attracting high-paying tourists while only having a slim percentage of hotel rooms that fit the luxury category is so fascinating. I’d even add that, by needing to attract luxury clientele, it would also drive up the cost of living for locals."

• "In a market trending towards the luxury traveler, your comments about the lack of true luxury stock seem particularly relevant to [The Garden Isle], which is generally lacking in luxury properties and brands."

The Legislative Grumble: Roofs & Red Tape

• "Regarding the convention center roof... it turns out that ignoring a leaky roof for a decade is a great way to turn a $27 million problem into a massive financial headache. For local hoteliers, the concern isn't just water damage; it is the erosion of market confidence. 'Maybe it won't rain on your gala' is a tough sell."

• "Deferred maintenance is what leads to added cost renovation! No surprise to those of us who know and get called in when it happens. They blew it BIG TIME!"

• "Darn shame. Consistency and stability of funding are needed for the Islands to keep their share of voice. It is a reminder that in local politics, even a strong run can end just short of the tape."

  • HHH Note: There’s nothing more expensive than a "cheap" fix that gets delayed for ten years. We’re currently watching a nine-figure masterclass in why proactivity matters.

The Design Crimes Division

• "I just got around to reading the newsletter and had to laugh out loud when I got to the half shower glass. I am in 100% agreement with you, worst design feature EVER in hotel redesigns!"

  • HHH Note: We will continue to campaign against the half-glass shower until every bathroom floor in Hawaiʻi is finally dry. It’s a design hill I’m willing to (slip and) die on.

Agree? Disagree? Have a hot take of your own? Fire back at dan@hawaiihotelhui.com, and your response might be featured anonymously in the next edition.

About Us

Hawaiʻi Hotel Hui was started by hotel industry veteran Dan Wacksman, CEO of Sassato, a Hawaiʻi-based consultancy that combines deep local expertise with a global perspective.

Our team brings decades of experience across operations, marketing, revenue, tech, and finance, all aimed at helping hotels and travel companies make smarter decisions and move faster. Whether you need additional expertise, extra horsepower, or just someone who thinks like you and moves things forward, we’ve got you. From local independents to global brands, we show up with a no-nonsense, results-focused mindset. To be blunt: we get sh*t done.

Recent projects include brand transitions, system selection (PMS, CRS, CMS — all the acronym soup), implementations, project management, feasibility studies, training, audits, and everything in between.

A lot of organizations deal with stretched teams, siloed processes, and messy tech stacks that quietly stall important work. We fix that. Happy to chat if this hits close to home.

Aloha {{first name |}}!

Welcome to the latest edition of the Hawaiʻi Hotel Hui Insider.

As we hit the Legislature’s May 7 finish line, we’re seeing the usual mix of last-minute pushes and quiet exits. The HTA funding reset had a real run this session… until it didn’t.

Before we dive into this issue, a big mahalo to our title sponsor for this quarter, Castle Resorts & Hotels. As CEO, Matt Bailey put it recently, this business isn’t about selling rooms, it’s about creating memories. Castle has been doing exactly that across the islands for decades, with a people-first approach that still shows up in the guest experience. We’re stoked to have them as part of the Hui.

In this issue, we look at the continued rise of soft brands (now heading to Kauaʻi), the growing push toward a luxury-first strategy, and what that actually means for a market where most inventory isn’t luxury. We also dig into Convention Center cost overruns, recent renovation activity across the islands, and where the latest wave of hospitality tech investment is really going.

Good intel is better when shared. Forward this to someone who needs to see it.

Relying on a forward for your news is a risky strategy. Join the Hui directly and get the signal sent straight to your inbox.

Mahalo for coming along for the ride!

Let’s dive in.

Mahalo,

Dan Wacksman
Hawaiʻi Hotel Hui Insider Editor-in-Chief 😄

Legislature Nears Finish Line… HTA Funding Doesn’t

In a previous issue, we talked about the Legislature’s sprint to the finish line. That sprint is about to end on May 7. That’s the hard stop, so anything still alive either gets pushed through in a rush… or quietly dies after months of debate.

One that most of the industry was hoping for: HTA Funding Reset (HB 1950). We’ve covered this in prior issues. The bill would’ve redirected a portion of TAT back to HTA and actually made a real run this session… before getting quietly tabled in Senate Ways and Means.

Encouraging momentum, followed by a very predictable ending.

Dead for now, but feels like a “see you next session” situation.

We’ll give a full breakdown of what passed and what didn’t in our May 19th issue.

Soft Brands Keep Coming… Curio Is Next Up in Kauaʻi

We’ve been tracking the soft brand wave across the islands for a while, and Hilton is finally planting its Curio Collection flag here in Hawai’i. Hale Hōkūala Kauaʻi is slated to open in Fall 2026 (the website says November), adding a 210-room new-build within the 450-acre Hōkūala resort in Līhuʻe. Timbers Kauaʻi has long anchored the residential side of the property. 

As with most soft brand plays, the pitch is local identity with global distribution… or as we like to call it, “fewer brand rules, same fees.” 

Jon Itoga has been named general manager, stepping in to lead the pre-opening team. Jon was most recently at Waikīkī Beach Marriott as the Hotel Manager. Congrats Jon!

For those keeping score, Curio is Hilton’s not-quite-luxury but higher-end soft brand, roughly in line with Marriott’s Autograph Collection. See our last issue for a brand scoreboard.

Stop Gifting Your Guests "Island-Scented" Chemicals
-Sponsored-

Let’s be real: guests know the difference between a generic lotion made on the continent and the real thing. If you’re still stocking vanity kits filled with synthetic fragrances, you’re missing a chance to anchor your brand in true place-based luxury.

Based in Waimea, Ua Hawaiʻi has spent 30 years perfecting clean, vegan skincare powered by native ingredients like kukui oil and botanical infusions.

These aren’t just "amenities", they are high-performance products that reflect your property’s quality. They already grace the counters of Hawaiʻi’s top-tier resorts because they deliver actual authenticity. It’s time to ditch the "aloha-wash" and give guests something they’ll actually want to take home.

Luxury Strategy… Built on ~20 Hotels?

A recent PBN article highlights what’s becoming a familiar refrain from industry and policy leaders: focus on the luxury traveler, as if we can just manifest a Four Seasons on every corner and call that strategy.  We’ve talked before about the myth of the “right tourist,” and now we seem to be doubling down with a luxury-first narrative that ignores a pretty inconvenient truth: roughly 82% of Hawaiʻi's hotel inventory is not luxury, while true luxury makes up maybe 18%.

Yes, Luxury has been crushing it, with statewide ADR of around $750 in January 2026 and February 2026.

No argument there. But building a statewide strategy around a sliver of inventory is like optimizing your rates based on your best suite. The reality is that most operators are running Courtyards, not Ritz-Carltons, and the playbook should probably reflect that.

We're not Monaco. We're not St. Barts. We're a broad-based market with a long tail of midscale products doing the heavy lifting. So when the strategy becomes "let's just attract luxury travelers," it's worth asking: to where exactly?

Yes, we have some incredible properties. Some of the best in the world. But they represent a handful of hotels statewide (~20 by my count). Meanwhile, most properties sit in that midscale range to upper upscale.

None of this is to say we shouldn't invest in quality, experience, or rate growth. We should. But there's a difference between elevating the product and pretending the market is something it's not.

Because at some point, the math wins.

Convention Center Cost Overruns? Who Could Have Imagined?

The Hawaiʻi Convention Center is officially under construction, but don’t hold your breath for a leak-free reopening in 2028. Lawmakers previously approved $100 million for long-overdue repairs, yet the rooftop terrace alone has already ballooned from $64 million to at least $87 million (and up to $110.5 million with contingencies). Meanwhile, a $55 million request for additional leak-related fixes was just pulled from the budget.

It’s a classic case of deferred maintenance coming home to roost. Back in 2017, this was a ~$27 million problem. Today, it’s… not. And even with all this spending, there’s still no guarantee the leaks are fully resolved. Meeting planners are paying attention, and with 2028 bookings actively being decided, the real risk isn’t just water coming through the ceiling; it’s confidence leaking out of the market. The Legislature should be focused on oversight and making sure the money is well spent, not pulling funding based on their deep expertise in construction and waterproofing (tongue firmly in cheek).

Read More

Some Recent Renovation News

• Courtyard by Marriott Waikīkī Beach – Completed multimillion-dollar renovation of 405 guest rooms, along with refreshed public spaces. Read More

• Pagoda Hotel (Honolulu) – Completed property-wide refresh of 199 rooms, updated interiors and public spaces, restored koi ponds, and introduced new dining tenants including Rainbow Drive-In and Paris Baguette. Read More

• Outrigger Waikīkī Beach Resort – Undergoing a $100M, 524-room phased renovation set for completion in late 2026, marking the brand’s fourth major Waikīkī refresh since 2018. Read More

• Coco Palms Resort (Kauaʻi) – Just kidding… At this point, it’s more legend than project.

Renovation Translation Table:

• Refresh – The “we had a little budget left” special. Paint, maybe some artwork, and a deep clean that should’ve happened anyway. May include some soft and hard goods.

• Soft Goods Renovation – New carpet, curtains, bedding, maybe a chair if we’re feeling generous. Same room, we just changed the outfit.

• Hard Goods Renovation – Furniture, case goods, bathrooms, fixtures. This is actual money being spent, not just a trip to the design showroom clearance rack.

• Multi-Million Dollar Renovation – Usually means “low” multi-millions. If it were $50M+, trust me… they’d tell you.

• Full Renovation – Everything short of knocking the building down.

• Phased Renovation – We’re renovating while staying open with earplugs as the new amenity.

And once any of these are done, you can officially declare that the hotel has been “reimagined.” 😉

RIMPAC Reality Check

In last issue’s poll, readers weren’t exactly bullish. Just 16% think RIMPAC proceeds as planned, while 34% expect it to be significantly reduced, 28% see a slight scale-back, and 22% are predicting a full cancellation. Net: most of the industry is expecting some level of disruption, which means summer may be on sale.

Big Shoes to Fill on Kauai

We previously reported the retirement of longtime leader Sue Kanoho after nearly 30 years at the Kauaʻi Visitors Bureau, big shoes to fill, no question.

Stepping in is Samira Siale, bringing a mix of hospitality, operations, and recent leadership at HLTA Kauaʻi. Her early message centers on community well-being, cultural respect, and long-term destination health, all the right notes.

Congratulations and Aloha to Samira.

New GM at Hilton Waikoloa Village

Hilton Waikoloa Village has named Nicholas Kuhns as general manager, bringing in an operator with deep luxury and resort experience across Hawaiʻi and the continent.

Most recently at Montage Kapalua Bay, Kuhns also previously led Royal Lahaina and held earlier leadership roles with Hilton on the mainland. Solid résumé, strong brand background, and now a big job ahead at one of the Big Island’s more complex resorts, where you not only need to keep the rooms clean, but also need to literally keep the trains on time (and on different tracks)! 

Congratulations and good luck!

Asset-Light Is Great... If You're Not the One Holding the Asset

The hotel industry loves talking about asset-light strategies. Brands shed real estate, collect fees, grow faster, and Wall Street rewards them handsomely. Marriott, Hilton, Hyatt, and now Accor (which just sold its ~31% stake in Essendi to Blackstone for roughly $1.1 billion) are all racing toward the same finish line. The logic is clean: own the brand, not the building.

(Quick reminder if you're new here: asset-light means the brand collects fees for its name, systems, and distribution but doesn't own the building. Someone else does.)

But at ALIS earlier this year, IHG CEO Elie Maalouf said the quiet part out loud: "If somebody isn't willing to be asset heavy, then the asset-light game stops." And he's right. Somebody has to hold the building, absorb the capital costs, carry the debt, and weather the storms while the brands print fee income and post record stock gains. The numbers tell the story pretty clearly: over the past five years, the major lodging companies have dramatically outperformed the hotel REITs that actually own the real estate they operate.

Marriott CEO Tony Capuano acknowledged it directly: "There is urgency around making these investments as compelling to our partners as they once were, because that's not where they are." The brands know owners are getting squeezed, and some are starting to examine franchise fees and procurement costs to ease the pain. Whether that's enough is a different question.

For Hawaiʻi, where most hotels are owned by REITs, private equity, and institutional capital (we've covered this extensively), the brand/owner tension is very real. Owners here carry capital costs, navigate state and county regulatory pressure, absorb labor and utility expenses that keep climbing, and then hand a percentage of the top line to a brand that won't be called when the roof leaks.

Asset-light is a brilliant business model. Just ask the brands. The owners might give you a different answer, unless, of course, they are banking on the flip.

Read more: Hyatt, Asset Light, Accor

Half Doors, Half Showers, Full Regret

A recent WSJ piece highlighted a trend that makes me wonder if hotel designers have ever actually stayed in a hotel: the push to ditch bathroom doors entirely.

Apparently, "open concept" now means your vanity, toilet, and bed offer a new level of togetherness that precisely nobody asked for. There are things you just don't need to watch your spouse do, and a hotel stay shouldn't change that. But while the industry debates whether a door is an "obstacle to flow," I’d like to pivot to my personal favorite: the half shower glass.

It may look good in architectural renderings, but in real life, you are essentially showering directly into the bathroom; the floor is soaked, the towels are wet, and the pro forma was likely the only thing that benefited. At some point, we have to ask if we are designing for guests or for spreadsheets. And we wonder why people often prefer Airbnb.

I am going on the record: the half-shower glass is my personal #1 hotel pet peeve. What is yours?

$1 Billion Into Hospitality Tech. Now What?

Abode Worldwide (not related to Adobe, the tech company) just dropped its 2026 Hospitality Tech Investment Index, and the headline number jumps out: 40 hotel tech companies raised a combined $1 billion between April 2025 and March 2026. Sounds like a surge… until you look closer. Property management systems led with about 40% of total capital, but Mews alone raised $300 million, meaning one company drove nearly a third of all funding. As we covered in a previous issue, that single raise ends up skewing the entire category. Mews is strong in Europe, gaining traction on the continent, but has few customers here in Hawaiʻi. 

The top raises tell a clearer story: Mews ($300M, PMS), Kindred ($85M, home swapping), Canary ($80M, guest experience), Duve ($60M, guest experience), and Wander ($50M, luxury rentals). Two of the top five going to guest experience platforms isn’t a coincidence. AI messaging, digital check-in, and upsell tools have officially moved out of the “nice-to-have” bucket.

Zoom out, and the breakdown gets interesting: PMS (~40%), alternative accommodations (~29%), guest experience (~15%), everything else (~11%), and revenue management… just 3%. For something we all obsess over, that’s surprisingly low. Either the category is maturing, or it’s being overlooked. Worth keeping an eye on.

BTW… rooting for our own Hawai’i-grown guest experience platform start-up platform Abra to show up on this list next year.

Turn Hawaii Trip Planners Into Direct Bookings
-Sponsored-

Hawaii.com reaches visitors while they’re choosing islands, building itineraries, and deciding where to stay, before they ever compare prices on Expedia or Booking.

We help hotels show up at that critical moment through ads, sponsored articles, itinerary placements, and native recommendations integrated directly into trusted travel content.

Instead of competing on price, you influence the decision early, when travelers are still forming preferences.

If you want more qualified visibility and a smarter path to direct bookings, we can help.

Industry Events

Ask Me Anything: Leadership Secrets Behind Hawaii's Top Hospitality Leaders

Join HSMAI Hawaiʻi for a candid “Ask Me Anything” session with Hawai‘i’s top hospitality leaders as they share real-world insights on leading and succeeding in today’s market.

Date: Thursday, April 23rd, 2026 Location: Prince Waikiki Time: 9:30–11:45 AM

• Ask Me Anything: Leadership Secrets Behind Hawaii's Top Hospitality Leaders, April 23, 2026 (Oahu)

• Visitor Industry Charity Walk - May 2, 2026 (Oahu)

• Visitor Industry Charity Walk - May 2, 2026 (Kaua‘i)

• Visitor Industry Charity Walk - May 9, 2026 (Maui)

• The 6th Annual Hawai‘i Hotel & Restaurant Show - June 17-18th, 2026 (Oahu)

Full list of 2026 Hawaiʻi Events 

*If you have industry events to share, please email me at Dan@hawaiihotelhui.com.

Spotlight on Hawai‘i Hospitality Opportunities

• Market Manager - Priceline (Hawai’i - Remote)

• General Manager - Grand Wailea, A Waldorf Astoria Resort (Wailea)

• Area Marketing Manager - Outrigger Hospitality Group (Hawaiʻi Island)

*If you happen to have any job openings, let us know. We will be glad to include them in the newsletter, space permitting; send the job link to Dan@hawaiihotelhui.com.

The digital mailbag was a bit heavy this week; overflowing with nostalgia, strategic skepticism, and a few "I told you so's." It’s clear the Hui isn’t just skimming; you’re dissecting every move from Kapalua to the cloud. Whether you’re sending virtual high-fives or schooling me on the evolution of a property, I’m just glad to be the hub for the conversation.

As always, the views expressed here belong to the Hui. I’m just the curator making sure the "industry therapy" stays anonymous and the discourse stays sharp.

The Kapalua Chronicles (Full Circle Edition)
Our recent coverage of the Montage Kapalua Bay transition sparked a wave of "I was there when" stories. It seems the history of certain jewels is as complex as their ownership structures.

• “It’s interesting that no one is mentioning the fact that this was originally Marriott’s. It began as a Renaissance hotel, then was demolished and rebuilt into a private club and residence model under the Ritz-Carlton flag in 2005. Now, with Marriott taking it back, they’re not only facing that same structural challenge, but also competing with their own luxury brand just down the road. I truly hope they tap into the wealth of knowledge of what worked and what didn’t from its private club era. It’s a very special property. It deserves to thrive.”

• “I spent six months there at the Montage. It’s one of my favorite properties on the planet. But the fact that 80% of the properties are condos, with a very small percentage being an actual hotel, makes it very challenging for them to even make any money.”

AI: Collusion or Common Sense?
The debate over algorithmic pricing and AI agents is heating up, and the Hui has thoughts on whether we’re looking at a free market or a courtroom.

• “This will be an interesting case testing the limits of AI in many different forms. Collusion used to be two or more executives discussing rates and setting a strategy. AI, considering the AI actions of a competitor, would be the truest form of a free market. Pricing would fluctuate based on demand and rational decisions. Preventing hotels from looking at aggregate past data for their competitors seems not to be founded on science or logic.”

• “A bigger distribution engine widens the guest funnel. That will be felt by residents.”

Reality Checks from the Ops Trenches

• “Having run condotels most of my career, while ownership is complex, it’s often preferable to working in a property owned by a VC, where asset managers focus on how to shave $.00002 off a bar of soap and have often never worked in a hotel.”

• “If I never have to deal with another condo-hotel, it will be too soon.”

• “Love and respect the dirt/culture first, then roll in the ‘vision statement’.”

Virtual High-Fives (The Fun Stuff)

• “Another great edition of the Hotel Hui insider! I love it!”

• “I have been enjoying your newsletters. I wish there was one of these for every sector in Hawaiʻi…”

  • HHH Note: One sector is enough for my blood pressure, but mahalo for the vote of confidence!

Agree? Disagree? Have a hot take of your own? Fire back at dan@hawaiihotelhui.com, and your response might be featured anonymously in the next edition.

About Us

Hawaiʻi Hotel Hui was started by hotel industry veteran Dan Wacksman, CEO of Sassato, a Hawaiʻi-based consultancy that combines deep local expertise with a global perspective.

Our team brings decades of experience across operations, marketing, revenue, tech, and finance, all aimed at helping hotels and travel companies make smarter decisions and move faster. Whether you need additional expertise, extra horsepower, or just someone who thinks like you and moves things forward, we’ve got you. From local independents to global brands, we show up with a no-nonsense, results-focused mindset. To be blunt: we get sh*t done.

Recent projects include brand transitions, system selection (PMS, CRS, CMS — all the acronym soup), implementations, project management, feasibility studies, training, audits, and everything in between.

A lot of organizations deal with stretched teams, siloed processes, and messy tech stacks that quietly stall important work. We fix that. Happy to chat if this hits close to home.

Aloha {{first name |}}!

Welcome to the latest edition of the Hawaiʻi Hotel Hui Insider.

Whether we are watching brands swap logos at Kapalua or tracking the latest management shuffle in Waikīkī, it is clear the industry never sits still.

A big mahalo to our title sponsor for this quarter, Castle Resorts & Hotels. With decades in the game and properties across the islands, Castle continues to shape what hospitality looks like in Hawaiʻi, and we’re stoked to have them as part of the Hui!

In this issue, we break down the structural hurdles facing the St. Regis transition at Kapalua Bay and look at the management shuffle at the world’s largest Holiday Inn Express. We also explore the stacking effect of Kona lows and fuel spikes, and a new model for Hilton to bring independent brands under its flag.

Good intel is better when shared. Forward this to someone who needs to see it.

Relying on a forward for your news is a risky strategy. Join the Hui directly and get the signal sent straight to your inbox.

Mahalo for coming along for the ride!

Let’s dive in.

Mahalo,

Dan Wacksman
Hawaiʻi Hotel Hui Insider Editor-in-Chief 😄

Montage Out, St. Regis In… Same Old Condo Challenge at Kapalua Bay

On the surface, this looks like a simple brand and management switch. It’s not. What most of the coverage misses is that this was never built to be a traditional hotel. It started as ultra-luxury residential, think second homes with services, where owners could choose whether or not to enter a rental program.

Then it got messy. Whole ownership units, fractional Ritz-Carlton Club Residences, and inventory that came out of bankruptcy and was later consolidated and resold. At one point, the rental pool was a mix of whole owners, fractional owners, and whatever inventory ownership could piece together, layered across multiple operators. Not exactly a recipe for a consistent five-star experience.

Montage stepped in and tried to “hotel-ize” the asset, bringing structure, tighter standards, and segmenting top-tier units to drive rate premiums. Big units, great location, all the right ingredients, but fragmented ownership, inconsistent participation, and multiple rental managers meant guests weren’t always getting the same product, or even booking through the same channel (a quick search found several units listed on Airbnb).

To their credit, Montage brought structure and discipline to a complex asset. The core structural constraint, though, never went away: this is a condo-hotel trying to behave like a luxury resort.

What’s just as interesting is what wasn’t announced. No key money/investment, no unit buybacks, no ownership restructuring. Which means Marriott is stepping into the same structural challenges, just with a stronger brand and bigger distribution engine. And with several Marriott properties already in West Maui, they may end up competing with themselves for the same guests.

If they can align owners, control inventory, and enforce true St. Regis standards, there’s real upside. We’ve seen this move before. You can reflag it, rebrand it, and plug it into a bigger distribution engine, but you can’t easily fix what’s broken underneath.

Another Waikīkī Management Company Shuffle

As you may recall, we previously covered PM Hotel Group’s merger with Sightline Hospitality, which marked its entry into Hawaiʻi with three Waikīkī assets: Holiday Inn Express Waikīkī, Hyatt Place Waikīkī, and Queen Kapiʻolani Hotel. PM also lists two additional projects on the west side of Oʻahu as “coming soon,” signaling a broader push into the market.

Now, there’s been growing chatter locally that PM may be stepping aside at the Holiday Inn Express Waikīkī, with Springboard Hospitality potentially taking over management of what is often touted as the largest Holiday Inn Express in the world (~600 rooms). We haven’t seen a formal announcement yet, but it’s far from a well-kept secret.

When PM first entered the market, we questioned how a mainland operator would adapt to Hawaiʻi’s unique dynamics. If this shift plays out, management would move back toward a management company with deeper local roots.

When performance isn’t where it needs to be, changing the operator is often one of the first moves on the table for owners. Sometimes it works. Sometimes it doesn’t. Either way, the musical chairs continue.

As a reminder for those who don’t live and breathe hotels, a property typically has three key players: an owner, a brand, and a management company. In this case, ownership stays put, the brand remains Holiday Inn Express, and the only thing changing would be the management company, from PM to Springboard.

Stop Gifting Your Guests "Island-Scented" Chemicals
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Let’s be real: guests know the difference between a generic lotion made on the continent and the real thing. If you’re still stocking vanity kits filled with synthetic fragrances, you’re missing a chance to anchor your brand in true place-based luxury.

Based in Waimea, Ua Hawaiʻi has spent 30 years perfecting clean, vegan skincare powered by native ingredients like kukui oil and botanical infusions.

These aren’t just "amenities", they are high-performance products that reflect your property’s quality. They already grace the counters of Hawaiʻi’s top-tier resorts because they deliver actual authenticity. It’s time to ditch the "aloha-wash" and give guests something they’ll actually want to take home.

Kona Lows, War, Fuel Spikes… What’s Next, Locusts?

Just as Hawaiʻi’s visitor industry was starting to find its footing again, it got hit with a perfect storm, literally and figuratively. Kona lows wiped out bookings and stalled momentum heading into spring, while global chaos is now driving fuel prices up, pushing airfares higher, and threatening airline capacity. Layer in geopolitical instability, airport disruptions, and a still-soft international market (looking at you, Japan), and you’ve got a fragile recovery walking a tightrope.

The real issue isn’t any one event; it’s the stacking effect. When storms, rising costs, and global uncertainty hit at the same time, travelers don’t reschedule; they sit out entirely.

The one bright spot? Hawaiʻi’s safe destination” halo might pull demand away from international destinations… but that only works if flights stay affordable and consistent. If this makes you nervous, you might want to skip the next story.

RIMPAC Risk?

For those in the hotel space, RIMPAC is always on the radar. Held every two years in Hawaiʻi, it’s the world’s largest international maritime military exercise, bringing 25,000+ personnel from 20+ countries… and a whole lot of hotel demand.

There’s no clean number of room nights produced, but anyone in Waikīkī knows the impact. Thousands of rooms get absorbed, driving compression and pushing rates across the market.

Lately, I have been hearing from hotels that demand is a bit softer than usual for RIMPAC, and many feel that this year’s exercise could be scaled back, or worse, canceled, given rising global tensions and frayed alliances.

If that happens, we could see some “decompression” (yes, we’re calling it that), and with higher airfares already pressuring leisure demand, losing that block of reliable room nights is not ideal heading into summer.

For what it’s worth, the official line still points to full steam ahead, with plans for the “largest RIMPAC ever” moving forward as scheduled.

Outrigger Names VP of Americas (AKA Hawaiʻi)

Outrigger has appointed Steve Nickerson as VP of Operations for the Americas. He brings a background across Sonesta, IHG, and, most recently, Midas Hospitality, with experience spanning full-service, select-service, and extended-stay portfolios. He will report to EVP Operations, Mike Schaff.

According to the press release, he’ll oversee hotel operations across the region, focusing on performance, consistency, and alignment with brand standards. He’ll definitely have his hands full with the renovation in progress at Outrigger Waikīkī, juggling guest expectations while upgrading a busy, high-traffic property (for the old timers, yes, Outrigger Main).

While the title covers the Americas, all of the current properties in the region are, well… Hawaiʻi. Are they foreshadowing something?

Aloha Steve, and welcome to Hawaiʻi.

Hotel Performance

Quick Summary (So You Sound Smart in Meetings): Statewide through February, we’re slightly up in occupancy and ADR, translating to a modest RevPAR bump of 1.8%. Maui is filling rooms the old-fashioned way, discounting, but still holding an eye-popping $554 ADR and pushing RevPAR up 5%. Hawaiʻi Island is the quiet overachiever, driving rate, and leading the pack with 6.4% RevPAR growth. Oʻahu… well, treading water, down across the board with RevPAR off 2.4%.

Worth noting, with the latest “excursion” in the Middle East at the end of February, combined with the Kona low storms, March is likely to come in softer. And beyond that… your guess is as good as mine 🤷‍♂️.

*Hotel performance data will be published in the first issue of each month.

Click here for the full DBEDT breakdown: Seats, stays, and then some.

Code Share for Hotels?

Hilton rolled out its new “Select” platform (they call it a brand, but it’s really a platform) with Yotel, the UK-based hotel company with 23 properties, as its first partner, and this one is interesting; it isn’t just another soft brand.

Instead of individual hotels joining Hilton, entire brands plug in. They keep their identity, run their own operations, and tap into Hilton’s distribution and loyalty engine. Or in Yotel’s words: “access, not identity.”

The best analogy we can think of? Airline code sharing. Ever book a United flight and end up on ANA metal? Same idea. Yotel runs the hotel, and Hilton helps fill the rooms, giving guests more options within the Hilton ecosystem.

This goes a step further than your typical soft brand. It’s not about individual hotels signing up anymore; it’s entire brands plugging into the system. More brands, more inventory, more reach. Hilton calls it “network effect.” You could easily see independent brands looking at this closely, keeping their identity but adding a much bigger sales, marketing, and distribution engine behind it. Assuming the fee structure makes sense, of course, because if all you’re looking for is volume, OTAs already do that pretty well.

And the appeal is pretty clear. Brands get scale without giving up control. Hilton gets growth without owning anything new or dealing with pesky brand standards. The trade-off? Potential dilution of brand identity, added fees, and, for Hilton, less control over standards, though you could argue that the ship has already sailed.

Call it a brand, call it a platform, call it whatever you want. It’s a different model. And if it works, it won’t be the last.

Read More

Drive Direct Bookings from High-Intent Hawaiʻi Travelers
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Travelers come to Hawaii.com when they’re actively planning their trip, researching islands, building itineraries, and deciding where to stay. That’s the perfect moment to introduce them to your property. Our platform blends inspiring travel content with integrated ads, helping hotels connect with high-intent visitors before they ever land on an OTA.

Through premium advertorials, sponsored itineraries, native placements, and display opportunities, your hotel can be featured directly within the content travelers trust while they plan their Hawaiʻi vacation. It’s a powerful way to tell your story, stand out from competitors, and guide travelers toward booking your property.

If you want more visibility with qualified travelers and more direct bookings, Hawaii.com can help.

You Can’t Make This Stuff Up (Tourism Edition)

We’ve talked in recent issues about the real barriers to travel, visas, phone checks, and the growing perception that the U.S. just isn’t as welcoming as it once was. Layer in tariffs, geopolitical tensions, and ongoing conflicts, and the list of headwinds isn’t exactly getting shorter.

And now we have… this.

The U.S. has appointed Nick Adams as Special Presidential Envoy for American Tourism, Exceptionalism, and Values. The title alone requires a minute. A “special envoy” is typically a government-appointed representative tasked with promoting U.S. interests abroad, in this case serving as a global face for American tourism (and apparently, exceptionalism and values).

Adams is best known as a social media personality who brands himself an “alpha male,” with commentary on culture and politics that has drawn plenty of attention and criticism. At times, it almost feels like a parody. He was born in Australia and became a U.S. citizen in 2021, an interesting backdrop for a role centered on “American exceptionalism.”

The role, at least on paper, is to promote the U.S. ahead of major global events like the World Cup and the Olympics. Tourism as diplomacy. Cultural exchange.

At a time when the industry is already working to counter perceptions that the U.S. is difficult to enter or less welcoming, this is… a choice.

You can’t make this stuff up.

Read More
Nick Adams X Account

Why Your AI Might Be Making You Dumber

Two studies have been rattling around in my head lately, and together they tell a somewhat unsettling story.

The first, from Harvard Business Review, looked at how people actually use AI. Most treat it like an answer machine: ask a question, get a clean response, move on. Fast, efficient, and a little dangerous, especially when the answer is wrong, which happens more than people realize. The smaller group using it as a thinking partner, pushing back, asking it to challenge assumptions, forcing some friction into the process, catches those mistakes, and gets a lot more out of it.

The second story adds another layer. MIT published a paper earlier this year showing that even a perfectly rational person can develop strong confidence in a wrong belief just by chatting with an agreeable AI long enough. They called it “delusional spiraling” (sounds a bit like a new owner’s forecast model). Stanford followed up with a study in Science, testing 11 major models, including ChatGPT, Claude, and Gemini. Every single one was more agreeable than a human, nearly 50% more, even when users described behavior that was flat-out wrong. People who got flattering responses walked away more convinced they were right and less willing to reconsider.

Put those together, and the picture gets uncomfortable fast. If you’re using AI to do your thinking for you, and the tool is designed to keep you happy, you’re not just saving time; you’re reinforcing your own assumptions while getting more confident in the process.

I keep telling everyone to start using these tools, and I stand by that. But the caveat matters: don’t use it as an answer machine. Use it as a sounding board. Correct it. Disagree with it. Ask it where you’re wrong. Have it argue the other side. If you’re not pushing back, you’re probably just reinforcing what you already think.

Same tool. Two very different outcomes.

Read the HBR piece | Read the MIT paper | Read the Stanford study

The End of Booking Engine Fees
-Sponsored-

For years, booking engine fees have quietly chipped away at hotel profits. Tambourine One puts an end to that.

When Tambourine powers your website and booking engine, you eliminate transaction fees and replace costly third-party vendors with one streamlined solution.

Lower costs. Better performance. More revenue that actually stays yours.

Industry Events

Ask Me Anything: Leadership Secrets Behind Hawaii's Top Hospitality Leaders

Join HSMAI Hawaiʻi for a candid “Ask Me Anything” session with Hawai‘i’s top hospitality leaders as they share real-world insights on leading and succeeding in today’s market.

Date: Thursday, April 23rd, 2026 Location: Prince Waikiki Time: 9:30–11:45 AM

• Tourism Day at the Capitol, April 10, 2026 (Oahu)

• 2026 Travel Weekly Hawaiʻi Leadership Forum - April 21, 2026 (Oahu)

• Visitor Industry Charity Walk - May 2, 2026 (Oahu)

• Visitor Industry Charity Walk - May 2, 2026 (Kaua‘i)

• Visitor Industry Charity Walk - May 9, 2026 (Maui)

• The 6th Annual Hawai‘i Hotel & Restaurant Show - June 17-18th, 2026 (Oahu)

Full list of 2026 Hawaiʻi Events 

*If you have industry events to share, please email me at Dan@hawaiihotelhui.com.

Spotlight on Hawai‘i Hospitality Opportunities

• Remote Hawaii Complex Group Sales Manager - Alohilani Resort Waikiki Beach (Honolulu)

• General Manager - Grand Wailea, A Waldorf Astoria Resort (Wailea)

• General Manager - Mauna Lani, Auberge Collection (Hawaiʻi Island)

• Area Marketing Manager - Outrigger Hospitality Group (Hawaiʻi Island)

*If you happen to have any job openings, let us know. We will be glad to include them in the newsletter, space permitting; send the job link to Dan@hawaiihotelhui.com.

Every issue, I tell myself I’ll skip this section if nothing is interesting. And every issue, you all prove that wrong.

I read every single note that comes in, even the ones that call me out. Mahalo for the support, the reality checks, and the occasional stroll down memory lane.

Here is what is landing in the inbox lately.

Praise (The fuel that keeps us going)

• “Aloha Dan, didn’t realize you were behind Hotel Hui. Not surprised [you're] quite the [entrepreneur]. Will definitely follow; keep up the good content!”

• “The podcast is finally happening! Congrats on the first episode.”

• “I always look forward to your newsletters! 🤙🌺”

Strong Opinions & Industry Takes

• “Real shifts are happening in the industry. Local operators need to stay adaptable as these ownership changes unfold. 🌴”

• “Interesting that [a] software company [Mews] in the hotel space is getting this funding and valuation… at the same time, publicly traded software companies… are getting slaughtered in the stock market…”

• “What is the top-line the company [Mews] is realizing? It's probably based on room count or users. Hard to see the margins justifying the valuation… But great for the company, if they can raise that much cash.”

• “This will be an interesting case testing the limits of AI in many different forms. Collusion used to be two or more executives discussing rates and setting a strategy.”

From the Ops Trenches (This One Hit Home)

• “When [a Hotel I worked at] opened in 2010, payroll and staffing were… calculated based on rooms sold… I still remember the graph showing daily occupancy and payroll expense… sent to ownership on a weekly basis.”

• “It took some time for owners to understand why Housekeeping labor lagged peak occupancy by a day… but the relationship between business levels and hourly labor was an absolute focus.”

Agree? Disagree? Have a hot take of your own? Fire back at dan@hawaiihotelhui.com, and your response might be featured anonymously in the next edition.

About Us

Hawaiʻi Hotel Hui was started by hotel industry veteran Dan Wacksman, CEO of Sassato, a Hawaiʻi-based consultancy that combines deep local expertise with a global perspective.

Our team brings decades of experience across operations, marketing, revenue, tech, and finance, all aimed at helping hotels and travel companies make smarter decisions and move faster. Whether you need additional expertise, extra horsepower, or just someone who thinks like you and moves things forward, we’ve got you. From local independents to global brands, we show up with a no-nonsense, results-focused mindset. To be blunt: we get sh*t done.

Recent projects include brand transitions, system selection (PMS, CRS, CMS — all the acronym soup), implementations, project management, feasibility studies, training, audits, and everything in between.

A lot of organizations deal with stretched teams, siloed processes, and messy tech stacks that quietly stall important work. We fix that. Happy to chat if this hits close to home.

Aloha {{first name |}}!

Welcome to the latest edition of the Hawaiʻi Hotel Hui Insider.

Whether we are watching the legislative wrangling or tracking the relentless multiplication of hotel brands, one thing is clear: the industry never sits still.

Before we dive in, a big mahalo to our quarterly title sponsor, Allana Buick & Bers (ABB). While we talk strategy, ABB ensures your HVAC and mechanical systems don’t fail. They help Hawaiʻi owners shift from "fixing what’s broken" to proactive engineering, allowing your team to stay focused on the guest experience.

We are also incredibly excited to launch our new podcast, "Three Questions." It’s a short video series where we talk with the people actually working on the ground in Hawaiʻi’s hotel and tourism industry: no panels, no talking points, just three direct questions and a real perspective.

In our inaugural episode, we sit down with Jerry Dolak, Director of Safety and Security at Hilton Hawaiian Village Waikiki Beach Resort. We dive into the biggest issues facing the local industry, how to prepare for unexpected crises (especially for independent hotels), and some wild highlights from his 20-plus-year career. If there is someone you think we should talk to, let us know!

This issue is packed with industry news and a few reality checks. We break down Castle’s quiet strategy of stacking “singles and doubles” to move the scoreboard and look at the ongoing Maui Bill 9 saga. We also explore the possibility of Hawaiʻi losing its hotel tax crown and ask why the big hotel companies suddenly need so many dang brands.

Want to get in front of Hawaiʻi’s hotel decision-makers? We have a handful of sponsorship spots opening up. Click below to see if we're a match.

Good intel is better when shared. Forward this to someone who needs to see it.

Relying on a forward for your news is a risky strategy. Join the Hui directly and get the signal sent straight to your inbox.

Mahalo for coming along for the ride!

Let’s dive in.

Mahalo,

Dan Wacksman
Hawaiʻi Hotel Hui Insider Editor-in-Chief 😄

Castle Stacking Singles and Doubles

For a company that tends to fly under the radar, Castle Resorts & Hotels has been quietly stacking wins lately.

In recent years, the company has leaned more into vacation condos and rentals, but lately it’s been stringing together a series of notable moves in the hotel space. You might recall that we recently reported that two of their managed properties, ISO in Kauaʻi (~79 rooms) and the Hilo Hawaiian (~286 rooms), were converted into Wyndham’s Trademark Collection soft brand, gaining global distribution while still operating as independent-style hotels. Whether joining a soft brand ultimately moves the performance needle or simply adds a layer of brand fees is a calculation every owner has to make, but it certainly raises visibility.

As we previously reported, Castle also recently picked up the management contract for the Waikiki Circle Hotel (104 rooms) and has now added two more Oʻahu properties owned by Hawaiʻi developer Peter Savio: Bishop Suites at the Executive Centre (~ 30 rooms) in downtown Honolulu and the Waikiki Heritage Hotel (~ 60 rooms) on Beach Walk.

While others chase trophy assets, Castle is stacking solid singles and doubles that move the scoreboard, while leaning into its position as the local alternative.

Intent vs. Execution

As we discussed in previous issues, Maui’s Bill 9 phases out more than 6,000 short-term rentals on Maui over the next several years, on the premise that those units should return to the long-term housing market.

In late February, the Maui Planning Commission rejected a proposal that could have preserved about 4,500 of those units as short-term rentals by creating new hotel zoning categories for properties that function more like visitor accommodations than housing.

That does not kill the proposal to create these “carve-outs”, but it makes the path harder because the County Council would now need a two-thirds vote to move it forward.

Bottom line: the housing goal is still colliding with the reality that many of these units have long operated as visitor lodging, and may not even be suitable for long-term housing. While Bill 9 is now law, the outcome is far from settled, and the next major moves will likely come from the courts.

Like much legislation, the intent is good, but the execution is flawed.

The End of Booking Engine Fees
-Sponsored-

For years, booking engine fees have quietly chipped away at hotel profits. Tambourine One puts an end to that.

When Tambourine powers your website and booking engine, you eliminate transaction fees and replace costly third-party vendors with one streamlined solution.

Lower costs. Better performance. More revenue that actually stays yours.

Right Pocket, Left Pocket, Slow Progress

The Green Fee Advisory Council has released its recommended package of 75-project recommendation package totaling $126.4 million, focused on resilience, stewardship, and tourism management. The list runs the gamut from native species restoration and cesspool conversions to beach restoration.

The current fight (and yes, there is a current fight) is not really about the projects, but about how the first round will be funded. Lawmakers are pushing back on the administration’s plan to fund the projects with $42.2 million in bonds instead of paying directly from the new Green Fee revenue. In other words, the same projects, a different pocket, and suddenly everyone has concerns. Nothing like a good bureaucratic fight to slow things down.

There is also a transparency issue. HB1949 was introduced to create a Green Fee transparency program and public dashboard, which is a polite way of saying lawmakers want a better handle on where the money is going. Theoretically, this is a great idea, but we wonder how much the transparency will cost.

Read More

Deep Dish, Wrigley Field, and Highest Hotel Taxes

Chicago hotels are backing a proposal to raise their room taxes by 1.5 percentage points, from 17.5% to 19%, which would make them the highest in the U.S. (for comparison, Hawaiʻi’s combined Transient Accommodations Tax is about 14%, though the state’s General Excise Tax pushes the effective burden closer to 20%). The increase would generate about $40 million a year, earmarked for marketing and convention sales.

They might want to take a lesson from Hawaiʻi, where the original Transient Accommodations Tax (TAT) was created to fund tourism marketing. Over time, however, that revenue began flowing into the state’s general fund instead of being reinvested in promoting the destination.

In a bit of irony here in Hawaiʻi, lawmakers are now considering a bill (HB1950) that would earmark a portion of TAT back to marketing. Amazing how twisted things can get.

The bigger question is why cities even need to do this. Tourism marketing should already be funded by the taxes visitors are paying today. What other industry sees its product taxed at nearly 20% and still has to ask for funding to promote the very demand those taxes depend on?

Read More

The Regulators are Sniffing Around Our Comp Sets

Competitive benchmarking is under the regulatory microscope, even if the legal theory feels like a stretch to anyone who has actually run a hotel.

In the U.S., the major class-action suit against the big brands and STR (CoStar’s hotel benchmarking platform that compares metrics like price and occupancy across a set of competing hotels) was dismissed last August because, as most operators know, looking at anonymized historical data is not exactly a criminal conspiracy.

Across the pond, however, the UK’s CMA (Competition and Markets Authority, Europe’s version of the U.S. antitrust regulators) has just launched its own investigation, eyeing Hilton, IHG, and Marriott for "reducing competitive uncertainty."

While in the US, the DOJ is still riding high from its RealPage settlement in the rental housing market, these hotel cases are struggling because benchmarking is what we have done since the days of mystery shopping and manual phone trees. If analyzing last night’s ADR is a crime, then a lot of revenue managers in Hawaiʻi are going to need very expensive lawyers. Then again, STR is pretty basic and is also backward-looking. When AI pricing algorithms can do far more, will those tools start to look closer to price fixing or collusion?

Want to dive deeper? Check out the CMA’s official launch notice for the UK perspective.

Drive Direct Bookings from High-Intent Hawaiʻi Travelers
-Sponsored-

Travelers come to Hawaii.com when they’re actively planning their trip, researching islands, building itineraries, and deciding where to stay. That’s the perfect moment to introduce them to your property. Our platform blends inspiring travel content with integrated ads, helping hotels connect with high-intent visitors before they ever land on an OTA.

Through premium advertorials, sponsored itineraries, native placements, and display opportunities, your hotel can be featured directly within the content travelers trust while they plan their Hawaiʻi vacation. It’s a powerful way to tell your story, stand out from competitors, and guide travelers toward booking your property.

If you want more visibility with qualified travelers and more direct bookings, Hawaii.com can help.

Another day, another brand

IHG just added Noted Collection, bringing its brand count to 21, and adding 11 new brands in 11 years. Which got us wondering: how many brands do the big boys need before someone stages an intervention?

• Accor: 53

• Marriott: 38

• Hyatt: 33

• Hilton: 25

• IHG: 21

• Wyndham: 18

Note: We actually went to the websites and counted!

Corporate headquarters will tell you this is about “consumer choice.” Supposedly, today’s traveler demands a hyper-specific brand for every mood, moment, and mattress preference.

But if you’re a little skeptical (and we are), the story may be less about guests and more about the math.

By launching more brands, companies like Marriott and Hilton can sign additional hotels in the same market without running afoul of territory protections. In other words, they get to compete with themselves, just under different labels. And if you’re wondering why all these soft-brand “collections” keep popping up, it’s because they let companies sign more hotels without enforcing strict brand standards that are expensive and often kill a property’s character.

So is this really about consumer choice, or market share, franchise fees, and keeping owners in the system?

The Adara–Sojern “Two Brand” Strategy Didn’t Last Long

RateGain has been busy shopping lately. In 2024, the company acquired Adara, a travel data cooperative that aggregates booking and intent data from airlines, hotels, and OTAs to power targeted programmatic advertising. Then, in 2025, it went bigger, buying Sojern for about $250 million, one of the travel industry’s largest digital advertising platforms.

At the time, the press releases promised the usual corporate comfort food: no changes, two brands, complementary platforms, etc. But anyone who has watched tech acquisitions before could read the writing on the wall.

Sure enough, RateGain is now folding Adara into Sojern, combining traveler intent data with the ad platform that turns that data into bookings. Strategically, it makes sense. If you own the data on who’s planning a trip and the engine that serves the ads, you control a pretty powerful piece of the travel marketing funnel.

Now comes the interesting part: watching how well RateGain digests the meal.

Claude is Having a Moment

Anthropic’s Claude is having a moment. Downloads jumped, web traffic spiked, and it briefly knocked ChatGPT off the top free spot in the U.S. App Store after Anthropic’s very public clash with the Pentagon. ChatGPT is still much bigger, but Claude is drawing fresh attention from developers, enterprise buyers, and users who liked Anthropic’s refusal to go along quietly.

Why is Claude getting more love? The product is part of it. Claude has built a strong reputation in coding and agent-style workflows, and Anthropic’s business-first model is resonating with companies that care more about output than chatbot fame. Anthropic is positioning Claude less as a chatbot and more as a work layer, with Cowork, Excel integrations, and plugins that sit directly inside business workflows.

You can even see the ripple effects in hardware. Developers experimenting with Claude’s coding agents and workflow tools have reportedly been scooping up Apple Mac minis as affordable local AI workstations (a safety precaution in case the AI goes crazy on your main workstation). When people start buying hardware to build around your platform, it’s usually a sign that it has moved beyond novelty.

I have not spent enough time on Claude yet. Most of my recent experimentation has been split between Gemini and ChatGPT. But over the next month, I plan to dig deeper into Claude, especially the workflow side.

Note: Amazon does not own Claude, but it is a major investor in Anthropic and its primary cloud and training partner through AWS.

AI Will Replace OTAs… Eventually

For the past year, there’s been plenty of chatter about AI agents bypassing OTAs and booking travel directly inside tools like ChatGPT. Turns out that it may take a little longer than expected.

OpenAI is reportedly backing away from building checkout directly into ChatGPT and will instead focus on discovery and search, leaving transactions to third-party apps. In other words, AI may help travelers plan trips, but actually completing the booking is still someone else’s problem (sound familiar, Google?)

Investors in Booking and Expedia seemed relieved. Both stocks jumped after the news, and Booking’s CFO recently noted that traffic from large language models remains “very small.”

So for now, OTAs are still in the driver’s seat. The AI revolution may start with trip inspiration, but the checkout page isn’t going anywhere just yet.

Read More

Industry Events

• Hawai‘i Tourism Authority's - 2026 Spring Update - April 1, 2026 (Oahu)

• 2026 Travel Weekly Hawaiʻi Leadership Forum - April 21, 2026 (Oahu)

• Visitor Industry Charity Walk - May 2, 2026 (Oahu)

• Visitor Industry Charity Walk - May 2, 2026 (Kaua‘i)

• Visitor Industry Charity Walk - May 9, 2026 (Maui)

• The 6th Annual Hawai‘i Hotel & Restaurant Show - June 17-18th, 2026 (Oahu)

Full list of 2026 Hawaiʻi Events 

*If you have industry events to share, please email me at Dan@hawaiihotelhui.com.

Spotlight on Hawai‘i Hospitality Opportunities

• General Manager - Grand Wailea, A Waldorf Astoria Resort (Wailea)

• Assistant Director of Housekeeping - Marriott International (Lahaina)

• General Manager - Mauna Lani, Auberge Collection (Hawaiʻi Island)

• Area Marketing Manager - Outrigger Hospitality Group (Hawaiʻi Island)

*If you happen to have any job openings, let us know. We will be glad to include them in the newsletter, space permitting; send the job link to Dan@hawaiihotelhui.com.

I’ve said it before, and I’ll say it again: this is my favorite part of the newsletter. Not because it saves me from writing a few paragraphs, but because it proves you all are actually paying attention.

The inbox was particularly lively after our recent deep dives into the Classic Vacations legacy and the ongoing Michelin debate. It seems everyone has a perspective on whether we are buying prestige or building a brand, and whether AI is our new best friend or just the latest gatekeeper.

Here is a look at what has been landing in the inbox lately: the praise, the reality checks, and the strong opinions. As always, these are kept anonymous so you can speak your mind without checking with HR first.

Praise (The fuel that keeps the lights on)

• "Love reading your wonderful newsletter that keeps me informed of all things hospitality."

• "Appreciate the newsletter each month. Thanks."

• "Loved the last issue of HHH, some great stuff in there, you always get me thinking."

The Michelin & "General Fund" Debate

• "The Michelin commentary is interesting. There’s always something better to spend it on, but the reality is that $1 million into the general fund equates to $.01 of value to all of us normal people. 90% is wasted by government inefficiency, and the remaining 10% doesn’t do anything to help our businesses."

• "Michelin … would be another marketing tool to bring people to Hawaiʻi.”

On the "Classic" Evolution

We were a bit taken aback by the response to the Classic Vacations/Ron Letterman story. We received comments from all corners of the industry, ranging from past employees to two CEOs.

• "[The analysis of Classic Vacations is] all true, but I think a bit over simplistic...there was a play in the Expedia construct, to combine technology, travel advisors, and high-end consumers; we just never got the chance to play it out."

• "What Classic under Ron's direction did for Expedia in Hawaiʻi was a turning point for how hotels were sold. I still remember the presentation as to why Expedia should be given the same wholesale terms."

• "[TBO] bought Classic Vacations because it's a beloved brand both amongst luxury suppliers and travel advisors alike... If we can combine Classic's brand equity and reach with new tools that help travel advisors leverage AI... we can truly make a difference."

• "Luxury has never been plug and play: it demands precision, service excellence, and human expertise. Together, we are elevating the standard... the future of luxury travel is advisor-centric."

Strong Opinions and Reality Checks

• “When you consider the damage our elected officials do in just 60 days, think how much better we’d be if they just met for a long weekend…“

• "AI is not becoming a new intermediary by default. It becomes one only when hotels do not control the introduction and identity upstream... AI interfaces will do the same thing [as OTAs] if demand still originates outside hotel ownership. The issue is not AI. The issue is who owns the guest relationship before comparison begins."

• "Older travelers and even travel agents still need personalized help and a brand they can trust and depend on. Combining high touch with high tech is a niche that will set you apart."

Agree? Disagree? Have a hot take of your own? Fire back at dan@hawaiihotelhui.com, and your response might be featured anonymously in the next edition.

About Us

Hawaiʻi Hotel Hui was started by hotel industry veteran Dan Wacksman, CEO of Sassato, a Hawaiʻi-based consultancy that combines deep local expertise with a global perspective.

Our team brings decades of experience across operations, marketing, revenue, tech, and finance, all aimed at helping hotels and travel companies make smarter decisions and move faster. Whether you need additional expertise, extra horsepower, or just someone who thinks like you and moves things forward, we’ve got you. From local independents to global brands, we show up with a no-nonsense, results-focused mindset. To be blunt: we get sh*t done.

Recent projects include brand transitions, system selection (PMS, CRS, CMS — all the acronym soup), implementations, project management, feasibility studies, training, audits, and everything in between.

A lot of organizations deal with stretched teams, siloed processes, and messy tech stacks that quietly stall important work. We fix that. Happy to chat if this hits close to home.

Aloha {{first name |}}!

Welcome to the latest edition of HHH. This issue, we have a lot in store for the hui.

The legislative sprint is officially on, and while we are watching the clock at the Capitol, some of our industry’s biggest players are quietly packing their bags for the continent.

Before we dive in, a big mahalo to our quarterly title sponsor, Allana Buick & Bers (ABB). While we talk strategy, ABB ensures your HVAC and mechanical systems don't fail you. They help Hawaiʻi owners shift from "fixing what's broken" to proactive CAPEX engineering, allowing your team to stay focused on the guest experience.

In this issue, we look at Trinity’s quiet exit to Florida, cover the 60-day sprint at the Capitol, and the results of our Michelin Guide debate. We also explore a $2.5 billion tech valuation that could reshape hotel operations (or just the math in pitch decks) and why 85 million people are suddenly panicking about AI.

Enjoy HHH? We’re opening a limited number of sponsorship slots. If you feel your brand is a good fit, click the link below, and we will reach out to you.

If you are getting value out of these updates, help us spread the word and forward this to a colleague!

Did someone forward this email to you? Don't leave your industry intel to chance. Join the Hui directly to make sure you never miss an update.

Mahalo for coming along for the ride!

Let’s dive in.

Mahalo,

Dan Wacksman
Hawaiʻi Hotel Hui Insider Editor-in-Chief 😄

Trinity Says “Aloha”… From Miami

Honolulu-founded private equity real estate firm Trinity Investments has relocated its headquarters to Miami, calling it a strategic move to position the firm closer to capital, partners, and key hospitality markets.

Founded in 1996, Trinity grew from a small three-partner shop into a global hospitality investor that has deployed more than $10 billion. Over the years, it owned marquee Hawaiʻi properties including The Ritz-Carlton Kapalua, Hyatt Regency Waikīkī, Fairmont Kea Lani, and The Kahala. Today, its only remaining Hawaiʻi hotel is The Westin Maui, acquired in 2017, while recent transactions have focused on Europe and the U.S. Sun Belt.

Trinity operates under a classic private equity model: raise institutional capital, acquire hotels to increase profitability, and eventually sell them for a return. Other PE companies active in the islands include KSL Capital, Blackstone, etc.

The firm says it remains interested in Hawaiʻi and will maintain a local presence. Fair enough. But zoom out, and the pattern is hard to miss: Hawaiʻi still hosts the hotels. Increasingly, the capital allocation and strategic decisions are made somewhere else.

Read More

Speed Lawmaking, Hawaiʻi Style

Before we dive into this year’s bills, a quick refresher on how the game works.

Hawaiʻi’s Legislature doesn’t sit year-round. It’s constitutionally capped at 60 “working days,” which stretches from mid-January to early May. That puts us on the shorter end nationally. A few states meet most of the year. Most others compress their lawmaking into 30 to 120 days.

We’re in the compressed window now. Hundreds of bills. Hard deadlines. Limited runway.

Plenty touch on hospitality and tourism. Here are a few worth watching:

• TAT Marketing Dedication (HB 1950) – Earmarks funding specifically for marketing.

• $25 per comp room (SB 241) – Would charge hotels for complimentary nights.

• Vacation Rental Enforcement (HB 1590) – Expands tools targeting illegal operators.

• Destination Management Restructure (HB 1947 / SB 2807) – Shifts tourism governance again.

• Michelin Guide Support (SB 2072) – Backs payment to bring Michelin recognition to Hawaiʻi.

If you feel strongly about any of these bills, or even just have a perspective, you can submit testimony directly through the links provided. Look for the orange “Submit Testimony” button.

At a recent conference, Tourism Committee Chairs Senator Lynn DeCoite and Representative Adrian Tam both noted how closely testimony is read and how it can influence discussion and amendments. It’s not symbolic. It’s part of the record, and in a 60-day sprint, it is a real way to have influence.

👉 List of Hotel and Tourism Bills to Watch

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Sheraton Waikīkī Says A Hui Hou to Tom Calame

After more than 30 years with Marriott International, Sheraton Waikīkī Beach Resort is bidding farewell to General Manager Tom Calame as he retires.

Tom’s career began in 1988 and took him through leadership roles across Latin America, Europe, the Caribbean, and Hawaiʻi. Since 2018, he has led not only Sheraton Waikīkī but the full Kyo-ya portfolio, including The Royal Hawaiian, Moana Surfrider, Sheraton Princess Kaiulani, and Sheraton Maui. He guided the group through COVID, major repositionings, and some of the most turbulent years our industry has faced.

Thirty-plus years. Five iconic Hawaiʻi resorts at the finish line. Not a bad run. A Hui hou, Tom.

Hotel Performance

Quick Summary (So You Sound Smart in Meetings): Demand is slightly up statewide, with the rate flat. Maui filled more rooms by cutting the rate. Hawaiʻi Island pushed rate and won (7.4% rev par growth!) Oʻahu is steady but uninspiring. Net result: modest RevPAR growth (2.5%), no breakout story.

Hotel performance data will be published in the first issue of each month.

Click here for the full DBEDT breakdown: Seats, stays, and then some.

Cartels, Conflict, and the Domestic Advantage

You’ve all seen the news out of Mexico. Following cartel violence, travel advisories were issued, and headlines moved quickly. Officials say order is being restored and major resort areas remain operational.

First and foremost, we hope for safety and stability for residents, visitors, and industry colleagues. No destination benefits from instability, and neither does our industry.

Tourism demand is highly sensitive to perception, but recovery depends on how contained and how prolonged the disruption is. In prior Mexico advisory spikes, where incidents were not directed at tourists, resort markets often saw short-term softness that stabilized within a booking cycle.

Closer to home, the Maui wildfires showed how quickly headlines can disrupt demand, even when impacts are geographically concentrated.

Mexico remains Hawaiʻi’s biggest West Coast leisure competitor. If coverage lingers, perception alone can influence booking behavior. Layer in U.S. involvement in Iran and rising global tension, and the travel picture gets murkier.

Historically, when Americans feel uncertain about the world, they don’t stop traveling. They adjust. International trips may get deferred. Familiar domestic destinations often benefit.

Hawaiʻi sits in that space. We are far, but we are still home.

This isn’t about rooting for instability elsewhere. It’s about understanding how sentiment shifts and working to our strengths.

Not so fun fact:

• The annual risk of being murdered in the United States is roughly 1 in 15,000.

• The annual chance of an American being killed in a terrorist attack abroad is approximately 1 in 2–4 million.

There’s a name for this: dread risk. We overreact to dramatic, unlikely threats and underreact to familiar ones. Think fear of shark attack vs. car accident.

Payroll as a Percent of Revenue? That’s Cute.

A recent hotel industry white paper made a point we’ve been circling for a while: The old staffing model is gone.

A few highlights that stood out:

• Wage elevation is permanent, not cyclical.

• Turnover is now a predictable operating expense.

• Luxury properties face the biggest mismatch between service expectations and available talent.

• Extended-stay models are outperforming in part because weekly housekeeping aligns better with workforce realities.

• Forward-looking operators are shifting from payroll as a percent of revenue to payroll per occupied room.

None of this should shock anyone operating in Hawaiʻi. We’ve already talked about hotel wages and benefits and an aging workforce pipeline.

The takeaway isn’t that labor is expensive. It’s that the operating model many of us built around abundant labor no longer exists.

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Ron Reads Hawai’i Hotel Hui

If you read the last issue of HHH, you may have seen my piece on Classic Vacations and its founder, Ron Letterman.

I was amazed that one of our readers forwarded it to Ron… and he replied!

I didn't expect he would remember our conversation (which he didn't), but it was definitely a good reminder of the impact you can have, even if you are not aware of it. Below is his email to me. (Published with Ron’s permission.)

Aloha Dan ,

A former employee of mine… sent me the article you wrote about our meeting so many years ago. I appreciate being remembered after all this time, and also appreciate the compliment, even though I do not really remember the specifics of our exchange. At the time of our meeting, the hotels were trying to adjust to the entrance of online booking agencies like Expedia and Priceline, and the traditional travel agency community was paranoid with fear, with many in the industry predicting the end of brick-and-mortar agencies. Now, companies like Expedia and Priceline are trying to adjust to the entrance of AI into their industry, and many are predicting their demise.

Click To Read The Whole Email.

Hotel Tech Bubble or PMS Revolution?

Hotel tech money is flowing again, this time it landed squarely on Mews. The cloud-based PMS (property management system - AKA brains of the hotel) just raised another $300 million, valuing the company at $2.5 billion. For context, that’s more than double what Sabre sold its entire hospitality business for.

The investor story is polished. Mews is positioning itself as a full hospitality operating system, not just a PMS, leaning hard into AI-native, agent-driven workflows. The press release cites 15,000 customers across 85 countries. If my back-of-the-envelope PMS math is even close, it’s hard to justify a $2.5 billion valuation on topline alone, never mind the bottom line.

PMS companies don’t win on funding rounds or vision decks. They win on reliability, integrations, and how rarely the front desk has to make an angry call at 2 a.m. 

Maybe Mews really is building the future of hotel operations. Or maybe this is venture math getting ahead of hotel reality. 

Either way, the valuation bar has officially been raised.

Why 85 Million People Stopped Scrolling

A recent AI essay titled Something Big Is Happening exploded online, pulling over 85 million views. It didn’t come from a household name. It came from a startup founder arguing that AI is moving faster than most people realize and that white-collar disruption may arrive sooner than expected.

This is not a new sentiment, but it went viral because it captured a real and growing anxiety. A sense that something is accelerating, and most people aren’t fully participating yet, and are getting left behind. The essay went on to give real and specific examples that people can relate to (and freak out about). 

The takeaway isn’t panic. It’s participation. 

Start using it! Draft an owner update. Analyze a STR trend. Build a sales outline. Test prompts with your revenue team. Play with it now, before your manager quietly replaces you with a prompt. (Half joking).

You don’t need a strategy deck. You just need to start.

Industry Events

• HSMAI Hawaii Networking Event - March 11, 2026 (Oahu)

• Tourism Day at the Capital - March 13th, 2026 (Oahu)

• Hawai‘i Tourism Authority's -2026 Spring Update - April 1, 2026 (Hold the Date)

• 2026 Travel Weekly Hawaii Leadership Forum - April 21, 2026 (Oahu)

• Visitor Industry Charity Walk - May 2, 2026 (Oahu)

• Visitor Industry Charity Walk - May 2, 2026 (Kaua‘i)

• Visitor Industry Charity Walk - May 9, 2026 (Maui)

Full list of 2026 Hawaiʻi Events 

*If you have industry events to share, please email me at Dan@hawaiihotelhui.com.

Spotlight on Hawai‘i Hospitality Opportunities

• National Sales Director / VP (Remote) – Hawaiʻi travel platform with surging traffic is hiring a senior ad sales leader to build partnerships across hospitality and tourism. Independent contractor role with uncapped earning potential and real runway.

  • Confidential retained search. Qualified candidates can email dan@sassato.com for more information.

• Hotel Assistant Manager - Prince Waikiki (Honolulu)

• General Manager - Grand Wailea, A Waldorf Astoria Resort (Wailea)

*If you happen to have any job openings, let us know. We will be glad to include them in the newsletter, space permitting; send the job link to Dan@hawaiihotelhui.com.

Last issue, reported on Senate Bill 2072, the proposal to use state general funds to pay for a Michelin Guide. We asked if Hawaiʻi should be footing the bill, and the results from our LinkedIn and newsletter survey are in.

The “Yes” camp edged it out at 52%, with 40% opposed and 8% on the fence. The vote was close. The commentary? Not even a little. Many of you made it clear that while our culinary scene may deserve the spotlight, taxpayer dollars might have higher priorities.

Here is what the Hui had to say this week:

The Michelin Drama

• "Just an update that the bill [Michelin Guide (SB 2072)] was deferred, and most likely will die. The oral testimony [was] embarrassing."

  • HHH Note: After reading this comment, it piqued our curiosity. We found the testimony online and quickly understood the reader’s concern. The presenter appeared unfamiliar with how Michelin actually operates. I suppose the old expression about two things you never want to see made, sausages and laws, still holds.

• "I don’t see the need for an investment (bribe) to bring the Michelin Guide to Oʻahu. There are far more important things for the legislature to spend money on. Visitors are generally not looking for haute cuisine, and locals know where to go. Your list should suffice for most people!"

• "There are some great chefs in the Hilo area, and striving to earn a Michelin star would only up the competitive game in my opinion."

The "Hui Approved" Must-Eat List
Since some of you think my list is better than a tire guide anyway (your words, not mine), here are a few more local spots recommended by the hui:

• "Regarding your restaurant list, I would include Mitch’s and Kats Sushi in the sushi section."

• "If you haven't tried Izakaya Tenkichi on King Street, you should. It's fun. And delicious."

Classic Memories: Ron Letterman
Our piece on Ron Letterman and Classic Vacations brought back some serious nostalgia, and some reminders that Ron usually knew what was coming.

• "I recall sitting in meetings when Ron said, 'The internet will never completely replace travel advisors.' That was in the late 90’s; crazy, right?"

• "Loved your article on Ron Letterman/Classic. After working with Ron... for several years, one thing I learned: Ron was always right. Always. It paid to listen to him. I was so fortunate to have him as a mentor for so many years."

Strong Opinions & Industry Notes

• On the AI Threat

  • "Very interesting; Hilton and Marriott view AI Chatbots as [a] potential threat to direct bookings. At the same time, many experts claim that these AI agents will open opportunities for hotels to increase direct business at the expense of the OTAs. If these bots don't book with the large brands and also don't book on OTAs... will there be new middlemen, which currently don't exist?"

• On the North Shore Dilemma

  • "The folks on the north shore need to decide if they want to be Lanaʻi or Molokaʻi. Few places are more rural than either island, but one supports an affluent population, and on the other, close to 35% are on public assistance."

The Virtual High-Five

• "Another great newsletter, thanks for the updates."

• "As always super!"

• "I have to say I was impressed with the quality of [the] articles and would enjoy continuing to receive them even though I am happily retired..."

• "Great newsletter, again!"

Agree? Disagree? Have a hot take of your own? Fire back at dan@hawaiihotelhui.com, and your response might be featured anonymously in the next edition.

About Us

Hawaiʻi Hotel Hui was started by hotel industry veteran Dan Wacksman, CEO of Sassato, a Hawaiʻi-based consultancy that combines deep local expertise with a global perspective.

Our team brings decades of experience across operations, marketing, revenue, tech, and finance, all aimed at helping hotels and travel companies make smarter decisions and move faster. Whether you need additional expertise, extra horsepower, or just someone who thinks like you and moves things forward, we’ve got you. From local independents to global brands, we show up with a no-nonsense, results-focused mindset. To be blunt: we get sh*t done.

Recent projects include brand transitions, system selection (PMS, CRS, CMS — all the acronym soup), implementations, project management, feasibility studies, training, audits, and everything in between.

A lot of organizations deal with stretched teams, siloed processes, and messy tech stacks that quietly stall important work. We fix that. Happy to chat if this hits close to home.

Aloha {{first name |}}!

Sue Kanoho broke the internet. Well, at least our corner of it. Our LinkedIn post on her retirement received 250+ reactions and 60+ comments (and counting), easily our most engaged post to date. That kind of response only happens when someone earns deep respect through decades of great work in Hawaiʻi’s visitor industry. Mahalo, Sue.

A big mahalo to our quarterly title sponsor, Allana Buick & Bers (ABB). While we obsess over the guest experience, ABB makes sure the hard systems actually work. They specialize in mechanical and HVAC CAPEX, helping owners move from reactive fixes to proactive engineering so you can focus on the guests.

In this issue, we look at Hawaiʻi’s growing cost pressures and what the latest numbers are really signaling. We cover the push to bring Michelin to the islands, the legal fight over Turtle Bay’s expansion, and a $227 million Kauaʻi resort now heading to auction. We also explore a shift that could reshape how guests discover and book hotels in the years ahead.

Special for our Subscribers! Our friends at Hawaii.com are relaunching and hosting a free cocktail event, and they are inviting subscribers to attend. It’s at ‘Alohilani on Feb 26! It will be a great time, and spots are limited, so RSVP before it fills.

If you find this useful, please forward it to a friend or colleague. We are building this community one reader at a time.

First time reading? Stop relying on forwarded emails and join the Hui directly. It’s free, and we promise no fluff.

Mahalo for sticking with us!

Let’s dive in.

Mahalo,

Dan Wacksman
Hawaiʻi Hotel Hui Insider Editor-in-Chief 😄

Two Rooms, One Message: The Math Isn’t Mathing

Governor Green preparing to scrap with Dan when asking him to subscribe to HHH  (Just joking, he could not have been nicer). 

Since the last newsletter, I attended PATA’s Annual Outlook and the AHLA Hospitality Show. Two rooms, different badges, same uncomfortable math.

At PATA, DBEDT’s forecast showed flat arrivals but stronger spending, largely driven by higher-income U.S. travelers. As previously discussed, the recovery is “K-shaped,” with affluent households driving premium travel while middle-income consumers pull back.

Japan remains challenged, and although total air seats are projected to inch up, virtually all of that growth is mainland-driven as international lift continues to erode. 2026 looks more like a holding pattern than a recovery, with any meaningful rebound not expected until 2027 or 2028.

At AHLA, the conversation turned to labor and affordability. We heard that hotel bartenders with tips can make $180K and housekeepers $72K, among the highest in the country, yet still not enough to comfortably live in Hawaiʻi. And for every $1 in wages, operators are layering on another $0.78 in benefits. Only luxury properties are meaningfully outperforming pre-2019 real ADR levels, reinforcing that same “K-shaped” divide we previously covered and also covered at PATA.

Jerry Gibson, Mayor Bissen (Maui), Mayor Kawakami (Kauaʻi), and Governor Green all discussed the housing crisis and doubled down on cracking down on illegal vacation rentals. The number floating around? 30,000 illegal units, with roughly 52 percent with out-of-state owners.

I also learned a new acronym, and I love my acronyms! ALICE, Asset Limited, Income Constrained, Employed. In other words, working, but still struggling.

We can’t just keep raising wages and hope the math works itself out. At some point, affordability, housing, and structural cost pressures have to be addressed. Governor Green acknowledged that directly and said it remains the key focus of his administration.

We love blaming one side or the other. Labor wants too much. Owners are too greedy. The government regulates too much. But hospitality still runs on a three-legged stool: fair wages for employees, fair returns for owners, fair rates for guests.

Often, the problem isn’t the legs. It’s the weight. Housing costs. Tax policy. Insurance. Airlift. When those pressures stack up, the stool doesn’t wobble because one leg failed. It wobbles because the load became too heavy.

You can raise wages. You can push rates. You can trim margins. But if the math keeps deteriorating, something has to give.

BTW - We have a lot of great associations here in Hawaii focused on Hotels and Tourism, the two mentioned in this article are the Hawaii Hotel Alliance (HHA) and Pacific Asia Travel Association (PATA). To see a list of industry-relevant associations, click here.

A Star Is Born… If We Write the Check

Ever wonder why some cities don’t have Michelin-starred restaurants? It’s usually not about talent. It’s about who’s willing to write the check.

Senate Bill 2072 proposes using state general funds to pay Michelin to create a Hawaiʻi restaurant guide. That’s how this works in most markets. Tourism boards or governments fund the guide, Michelin sends inspectors, and suddenly a destination is deemed “world-class.”

Supporters argue it boosts prestige and visitor spending. Critics question whether taxpayer dollars should support a private rating system owned by a French tire company. (Backstory: the Michelin Guide was started by a French tire company in 1900 to encourage people to drive more, travel farther, and quite literally wear down their tires.)  

Florida reportedly put up more than $1.5 million to bring Michelin in. Atlanta’s CVB paid around $1 million. Hawaiʻi’s bill leaves the dollar amount blank for now, but the funds would come from the state general fund and be handled by DBEDT. The Hawaiʻi Tourism Authority is supporting the measure.

The real question isn’t whether Hawaiʻi has world-class restaurants. We do.

The question is whether we should be paying for validation.

What do you think? 

BTW - If you want to check out my personal Michelin Guide of Oahu, you can find it here, wonder if the legislature will pay me a cool mill for it ;-). If you think I missed any great ones, or have neighbor island recommendations, please let me know! 

Read More

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The problem isn’t your dislike for digital marketing. Its lack of a clear, easy-to-implement strategy and a closed tracking loop that clearly shows MoM improvement, as well as what is and isn’t working.

Talk Agency is ready to roll up its sleeves and dig into your business to build an action plan that delivers results, not promises.

Book your free digital marketing clarity workshop with our founder, Cooper Jitts, to unlock new growth today.

Keep The Country, Waikiki?

When Host Hotels & Resorts bought Turtle Bay for $680 million in 2024, they weren’t just acquiring a trophy resort; they were buying expansion rights. Host reportedly paid an extra $50 million for a 49-acre parcel of “entitled” land approved for a few hundred additional rooms. Adding that many luxury keys would be a massive financial win for the REIT, but building in 2026 based on a 2013 environmental study is a bold strategy. The City determined the 375-room proposal fit within the scope of a larger 530-unit build-out analyzed in the 2013 EIS (Environmental Impact Statement) and concluded no further review was required. This month, community group Kūpaʻa Kuilima filed to stop the expansion. That $50 million “entitlement” may prove more complicated than originally bargained for.

Utah-based Arete Collective snagged a separate 65-acre parcel nearby for $43 million. They are already moving forward with The North Shore Club, a low-rise resort residential development with roughly 100 units in the early phases and plans for a 250-unit condo hotel down the road.

Since we love back-of-the-envelope math, here it is: the previous owners, Blackstone, purchased the property in 2018 for $332 million and poured a massive $250 million into renovations. Even after that quarter-billion-dollar spend, they exited in 2024 with approximately $768 million in total proceeds, roughly $186 million in profit. Not a bad payday, especially considering they passed the inevitable legal wrangling to the new buyers.

Blackstone did the heavy lifting on the renovations and timed the exit well. Now Host and Arete have to convince a North Shore community that “Keep the Country, Country” can coexist with a few hundred new keys.

A $227 Million Plan. Now at Auction.

A planned $227 million resort project on Kauaʻi’s South Shore is heading to auction before a single room is built.

Kupono Resort LLC bought 25 acres in Kukuiʻula in 2021 for $24.24 million, with plans for The ʻŌhia, an 85-room hotel and 65 residential units in phase one, followed by another 150 residences. The 2023 debut never happened. After filing Chapter 11 in July, the property is now up for bankruptcy auction, with bids due in April.

Read More

The (Maybe Not So) Slow Death of Metasearch

A benefit of aggregating and curating stories every month is that you start to see the throughlines. And here’s one that’s getting harder to ignore: the demise of metasearch may be accelerating.

Trivago, once powered by wall-to-wall TV ads and the creepy “Trivago Guy,” is now pivoting hard into streaming, podcasts, and AI-driven search. Revenue grew 27% in Q4, but EBITDA barely moved. Advertising spend was up 31%. Translation: Growth is expensive. Trivago is now trading at $2.90, way off its peak of $118.

TripAdvisor is fighting a different battle. SEO traffic is declining thanks to Google’s AI Overviews, and even management admits visitors are fading. The company is exploring “strategic alternatives,” which is corporate code for “we’re looking at options.” The stock dropped 18% on earnings and now trades under $10, a far cry from its peak of $110. Not exactly a vote of confidence.

And then there’s Kayak. Founder Steve Hafner is out as CEO after 22 years, ostensibly moving into an AI-focused role at Booking Holdings. Booking already took a $457 million writedown on Kayak, citing lower future cash flows and higher acquisition costs as Google’s AI products reshape search.

Notice the pattern?

Metasearch was built for a world where consumers typed in “hotels in Waikiki” and compared blue links. Today, travelers ask ChatGPT, Gemini, or Claude to build an itinerary, suggest neighborhoods, and summarize reviews. A grid of pay-for-play rates feels like showing up to an AI fight with a flip phone.

Metasearch still drives serious traffic and bookings. But if AI becomes the new front door to travel discovery, the old comparison engine may start to look like a very unsophisticated, very expensive middle layer.

Turns Out Ron Was Right

Skift recently referenced Classic Vacations in an earnings story about its new owner. I somehow missed that the company had been acquired (again) in late 2025, and seeing the name sent me down memory lane.

One of the first acquisition projects I was ever involved in was Classic Vacations (then known as Classic Custom Vacations). It was the early days of online travel, when everyone was trying to figure out how to bring traditional travel companies into the digital world.

It was my first real exposure to acquisition due diligence. On day one, all the VPs, SVPs, and C-suite folks from the potential acquiring company I worked for were on site. After a couple of days, they disappeared. And there I was, a lowly manager, rolling up my sleeves to actually understand how the business operated.

The legendary Ron Letterman, founder and CEO of Classic Custom Vacations, spotted me in the office and invited me to lunch. He skipped the pleasantries. He questioned the deal, the strategy, and whether the folks circling the company really understood what they were buying. He unloaded. I was shell-shocked, but I never forgot that conversation.

We passed on the deal. Expedia didn’t. Continue reading

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Stayntouch PMS helps hotels unlock revenue across the full guest journey, before arrival, at check-in, and throughout the stay, without adding complexity for staff or guests.

Here’s how hotels drive more revenue with Stayntouch:

• Convert more guests to direct: Digital registration cards and pre-check-in convert up to 15% of OTA guests to direct while creating new pre-arrival upsell opportunities.

• Monetize every stay: Mobile, kiosk, and staff mobility enable 3-way check-in plus automated upsells for early check-in, late checkout, upgrades, F&B, and add-ons.

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• Flexible booking, proven ROI: Hourly bookings and dynamic rates monetize unused inventory, with hotels achieving up to 253% ROI in months.

Expedia is at it again, layoffs that is

While hotels struggle to find labor, the OTAs are moving in the opposite direction. Expedia Group is starting 2026 with a familiar move: cutting staff in the name of “operating efficiency.”

Back in April, we reported on Expedia’s 500+ layoffs. A new WARN filing now confirms another 162 layoffs in Seattle. The cuts included numerous senior-level positions.

The message is clear. The platform has been consolidated. Now the focus is efficiency, automation, and fewer layers of expensive “human infrastructure.”

The reductions appear to be Seattle-based, so here’s hoping our crew on the islands remains unaffected.

AI Just Made Marriott and Hilton’s Risk List

For more than twenty years, Marriott and Hilton warned investors about OTAs. This month, they added a new risk: AI.

In their latest annual filings, both brands flagged large language models like ChatGPT as potential new intermediaries that could divert bookings away from direct channels and increase distribution costs. No AI platform is charging commissions today, but we all see where this is heading.

Hilton warned that major tech platforms entering the booking business could push demand away from direct channels. Marriott said AI-powered intermediaries could disrupt how guests plan, book, and pay, potentially eroding brand loyalty and raising costs.

Meanwhile, Google says AI-mode searches are already three times longer and increasingly conversational. More follow-up questions. Fewer clicks. The booking tools are not fully live yet, but discovery is already shifting inside the AI interface.

OpenAI has also begun testing sponsored placements inside ChatGPT trip-planning conversations, allowing travel brands to advertise directly inside the chat before a guest ever reaches a website.

Looks like we have some new, and old but reimagined, gatekeepers. And as my good friend Tim Peter wrote in Digital Reset, gatekeepers are gonna gate.

We spent two decades negotiating with Expedia and Booking.

The next negotiation might be with a chatbot.

Read More

Website + Booking Engine. One Seamless Experience.
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Some call it a website with a booking engine built in. Some call it a booking engine with a website built in. At Tambourine, they just call it one.

In a market as competitive as Hawaiʻi, every click counts. When a guest leaves your site and enters a disconnected booking path, you lose trust (and revenue).

Tambourine eliminates friction by merging the site and the engine into a single, high-converting organism. No confusion, just a direct path to a confirmed stay.

Industry Events

Help celebrate the relaunch of Hawaii.com
-Sponsored-

The team behind Hawaii.com is hosting an evening of food and cocktails to celebrate their recent relaunch. Learn more about their vision as they continue building a trusted platform for travelers and local partners.

Date: Thursday, February 26th Location: ‘Alohilani Resort Waikīkī Beach - SWELL Pool and Bar Time: 5:00–7:00 PM

Space is limited; if capacity is reached, you will be added to a waitlist and kept informed as the event approaches.

• 2026 Travel Weekly Hawaii Leadership Forum - April 21, 2026 (Oahu)

• MHLA 47th Annual Visitor Industry Charity Walk - May 9, 2026 (Maui)

Full list of 2026 Hawaiʻi Events 

*If you have industry events to share, please email me at Dan@hawaiihotelhui.com.

Spotlight on Hawai‘i Hospitality Opportunities

• National Sales Director / VP (Remote) – Hawaiʻi travel platform with surging traffic is hiring a senior ad sales leader to build partnerships across hospitality and tourism. Independent contractor role with uncapped earning potential and real runway.

  • Confidential retained search. Qualified candidates can email dan@sassato.com with a resume and relevant experience.

• Chief Brand and Narrative Officer - HVCB (Honolulu)

• General Manager - Highgate (Maui)

• General Manager, Sheraton Waikiki Beach Resort - Marriott International (Honolulu)

• Director of Revenue Management - Renaissance Honolulu Hotel & Spa (Honolulu)

• Resort General Manager - Westgate Resorts (Lahaina)

*If you happen to have any job openings, let us know. We will be glad to include them in the newsletter, space permitting; send the job link to Dan@hawaiihotelhui.com.

We are a few weeks into the year, and the inbox is already humming. I say it every issue, but the best part of this project is hearing from all of you. Whether you are correcting my math or schooling me on the nuances of condo boards, your feedback is what makes this a Hui.

Here is a look at what has been landing in the inbox lately.

Praise (The fuel that keeps us going)

• "Excellent information, Dan, and I love that you share your own feelings and opinions as well. Regardless of whether or not the audience agrees, it’s refreshing to have a perspective, and yours is respected and comes with credentials to back it up."

• "Just started reading your newsletter and am really enjoying it."

• "Another great newsletter. Thank you."

• "Love your synopsis. Thank you."

The Strategic Pulse

• "The hiring patterns reveal everything. While most companies debate AI strategy, the real players are investing in teams that can actually execute and deliver at scale."

• "World Cup may be the reason for hotels in several host cities knowing that they will miss full year 2026 budgets by the end of June [or] mid-July."

• "This Airbnb thing is getting more and more interesting: hotel acquisition... AI... Mahalo for keeping us informed."

Complexity and Reality Checks

• "Land: they usually don't make more of it. Except in the Maldives, where you see huge landfill projects being developed."

• "Another complicating factor in condo operations is the presence of rental boards, which often dictate to operators on how rentals should be managed."

• "Navigating the intricacies of hospitality law is no small feat: it's a true endeavor in understanding complex relationships."

• "Complexity can lead to confusion, especially in the hospitality industry. Clarity is essential."

Agree? Disagree? Have a hot take of your own? Fire back at dan@hawaiihotelhui.com, and your response might be featured anonymously in the next edition.

About Us

Hawaiʻi Hotel Hui was started by hotel industry veteran Dan Wacksman, CEO of Sassato, a Hawaiʻi-based consultancy that combines deep local expertise with a global perspective.

Our team brings decades of experience across operations, marketing, revenue, tech, and finance, all aimed at helping hotels and travel companies make smarter decisions and move faster. Whether you need additional expertise, extra horsepower, or just someone who thinks like you and moves things forward, we’ve got you. From local independents to global brands, we show up with a no-nonsense, results-focused mindset. To be blunt: we get sh*t done.

Recent projects include brand transitions, system selection (PMS, CRS, CMS — all the acronym soup), implementations, project management, feasibility studies, training, audits, and everything in between.

A lot of organizations deal with stretched teams, siloed processes, and messy tech stacks that quietly stall important work. We fix that. Happy to chat if this hits close to home.

Aloha!

We are officially settling into the rhythm of 2026, and if the inbox is any indication, the industry is already moving fast. The feedback on the last few issues has been incredible! Mahalo to everyone who has taken the time to read, reply, and challenge us. It’s exactly why we built this Hui.

A big mahalo as well to our quarterly title sponsor, Allana Buick & Bers (ABB). We talk a lot about "guest experience" in this industry, but nothing kills a guest experience faster than a broken chiller or a pipe burst in the lobby. ABB are the pros who keep that from happening. They specialize in the critical side of hotel ownership: mechanical and HVAC CAPEX. Instead of waiting for a crisis, they help owners assess, plan, and engineer fixes before the panic sets in.

In this issue: Wyndham Hotels tiptoes onto Kauaʻi, condo-hotel liability blows up in a very real and very litigious way, and we ask the obvious question about the Green Fee: Where’s the actual plan? We also break down what 2025’s numbers are really telling us, why New York’s so-called “junk fee ban” is mostly political theater, and a hotel tech rebrand that is signaling a new standalone chapter for a very familiar platform.

If you find this useful, please forward it to a friend or colleague. We are building this community one reader at a time.

New here? Join the hui below. It’s free.

Mahalo for sticking with us!

Let’s dive in.

Mahalo,

Dan Wacksman
Hawaiʻi Hotel Hui Insider Editor-in-Chief 😄

Wyndham Quietly Grows on Kaua’i

When Castle Resorts managed Hilo Hawaiian, which joined Wyndham’s Trademark Collection last year, it felt like a one-off. A soft brand landing on the Big Island, modest distribution upside, nothing seismic (Kilauea pun intended). But it turns out that may have been the opening move.

Castle has quietly added another one of its managed properties to the Wyndham Trademark Collection, The ISO (Island, Sky, Ocean). This is the first Wyndham hotel on Kauai. This does not include the 5 Kauai Wyndham Vacation Ownership inventory on Kauai, which, as we’ve noted before, is a separate publicly traded company, though it can be booked on the Wyndham website. 

Wyndham’s hotel presence in Hawaiʻi has always been light, especially compared to its sizable timeshare portfolio. Trademark Collection (a soft brand) offers a low-friction way in: keep the property’s identity, plug into Wyndham’s distribution and loyalty engine, and avoid the heavy brand standards that can be tough to justify.

For Castle, this looks like a pragmatic play, distribution without reinvention. For Wyndham, it’s another small step toward relevance in the Hawai’i market.

When Liability Explodes: The Messy Reality of Condo Management

We’ve spent a lot of time lately deconstructing the “who’s on first” puzzle of Hawaiʻi hotel ownership, branding, and management. From trusts that own the dirt to brands that don’t actually run the building. But if you think hotels are complicated, step into the world of condotels and vacation rentals, where a single property can involve multiple layers. That complexity turned very real and very litigious after last year’s horrific grill explosion at The Whaler on Kāʻanapali Beach, which injured more than a dozen people.

The resulting lawsuit reads like a masterclass in impleading, a legal term for suing everyone tied to the property. Plaintiffs have filed negligence and liability claims against the AOAO, Aqua-Aston, Marriott Vacations Worldwide, HEI Hotels & Resorts, Destination Maui, Inc., along with equipment manufacturers and the gas company. The allegation is that the “resort” failed to implement basic safety protocols. But zoom out, and the broader issue is hard to ignore: who actually is the “Resort”?

When a guest books a stay at a “branded” vacation rental, they reasonably assume a single entity is responsible. In reality, responsibility is spread across a tangled web of ownership structures, management agreements, and vendors that only becomes visible after something goes wrong.

Reality Check: Most condo properties with significant vacation rental activity involve multiple parties, since individual owners usually control how their units are rented. Those roles are often blurred, but here’s how they typically break down.

• Association of Apartment Owners (AOAO): The condo owners’ association that controls common areas, building systems, and shared operations.

• Front Desk / Common Area Operator: A company hired by the AOAO to operate the front desk, typically a management company that also markets and may brand the property. These operators often run their own on-site rental pool, and in some cases even own the front desk and some common areas outright. (In this case, HEI Hotels and Resorts)

• Branded Management Companies: Brand-affiliated operators that manage and market multiple units in a property for unit owners. (In this case, AquaAston and Marriott Vacations are examples).

• Unbranded Management Companies: Independent companies that manage and rent units on behalf of owners without a brand. (Think local real estate companies and small management companies).

• Self-Managed Units: Owners who operate and market their units directly, typically via Airbnb or VRBO.

I am exhausted just writing that, and that’s the simple version. The real one requires a whiteboard, a few lawyers, and a stiff drink

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Why hotels are switching:

• Save up to 80 hours a month by reducing manual tasks with intuitive workflows and built-in automation.

• Manage multi-property portfolios up to 70% faster with real-time visibility and control across locations from a single platform.

• Train new staff in under two days, so onboarding is faster, and consistency is easier to maintain, even with lean teams.

• Stay flexible and mobile, with a system that adapts to how your hotel operates.

Easy to use, built for operators, and focused on keeping teams efficient while delivering exceptional guest experiences.

Sue Kanoho Stepping Down After Three Decades

I had the chance to attend HVCB’s annual membership meeting last week at the Royal Hawaiian Hotel, which covered market updates, the new “Hawaiʻi Stays With You” campaign, and changes to the HVCB management structure. It was a solid, informative session and, as always, great to reconnect with industry friends old and new. 

A special and well-earned mahalo was given to Sue Kanoho, who is retiring after 29 years as Managing Director of Island Chapters and Executive Director of the Kauaʻi Visitors Bureau. Sue was sent off in style with a Proclamation from Governor Green and heartfelt words recognizing her lasting impact on Kauaʻi and Hawaiʻi’s visitor industry.  

Mahalo nui loa, Sue, for all you have done for Kauaʻi and Hawaiʻi’s visitor industry. Wishing you all the best in your next chapter.  

Green Fee: Still Waiting for the Plan

We’ve written before about the state’s new “green fee,” a 0.75 percent TAT increase projected to raise about $100 million a year and push Hawaiʻi’s tourism taxes to among the highest in the country. The pitch was clear: climate resilience, environmental protection, and more sustainable tourism. The concern was just as clear: whether the money actually stays dedicated, or eventually drifts into the general fund.

That question came up again in a recent NPR interview with Jeff Mikulina, chair of the Green Fee Advisory Council. According to Mikulina, the council reviewed more than 600 project proposals totaling over $2 billion in requests and has now sent a first-year funding portfolio to the governor. The focus is on ready-to-go projects with visible impact, particularly around wildfire mitigation, climate risk, and heavily impacted areas.

All of that sounds right. Hawaiʻi has heard similar promises before. Dedicated funds tend to be “dedicated” until budgets get tight. Cruise ship contributions are still tied up in court, federal funding has been pulled back, the Hawaiʻi economy is staring at a softer 2026, and the temptation to repurpose dollars never really goes away.

The green fee may be the right idea. But the real test is whether residents can actually point to meaningful projects and say, “That’s where the money went.”

Hotel Performance

Hotel performance data will be published in the first issue of each month.

Click here for the full DBEDT breakdown: Seats, stays, and then some.

Resort Fees Banned! - Don’t Believe the Headlines… Except Ours.

New York City Mayor Zohran Mamdani made headlines a couple of weeks ago by “banning” resort fees and junk fees. Look past the headline, and it is really no more than a PR event than a meaningful policy shift. To be clear, the new rule does not ban these fees. It simply requires that the total cost be disclosed upfront.

That requirement already exists. The FTC rule now in effect requires hotels to display total prices clearly, and most operators have been complying since earlier this year. In that sense, New York is largely reinforcing a federal standard rather than breaking new ground.

The real story here is time. Resort fees are not banned, but their days may be numbered. Once fees are fully baked into the advertised price everywhere, the economic advantage fades fast. No hidden margin. No OTA arbitrage. No “looks cheaper until checkout” trick.

So no, resort fees didn’t die this week. But the clock is clearly running. And like many bad industry habits, they probably won’t disappear in a dramatic headline moment. They’ll quietly wither away once they stop working, or morph into something else. Attribution-based selling, anyone? 

I’ve written before about booking fees and why they’re a problem. You can read that here.

It’s time to go all-in on direct.
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When destination resorts package with air, they can offer more competitive pricing, giving travelers another reason to book direct. Tambourine is helping hoteliers bring the convenience of “one-stop shopping” to hotel websites without handing the relationship (or margin) to an OTA.

• Create an OTA experience on your hotel site, smooth shopping, fewer clicks, less friction

• Offer a lower overall price through bundled air + stay

• Less than 5% cancellation on packaged bookings (because people commit when flights are involved)

2025 Was a Step Back. 2026 Looks Like a Grind

For the first time since 2020, U.S. hotel performance moved backward. CoStar’s final 2025 data shows occupancy down 1.2 percent to 62.3 percent and RevPAR slipping 0.3 percent. ADR rose slightly, but mostly just enough to keep up with inflation.

This slowdown was telegraphed months ago. CoStar, Tourism Economics, and PwC all downgraded their outlooks, and 2026 isn’t shaping up as a rebound year. Supply is growing faster than demand, costs remain elevated, and margins are tightening. Growth now has to be earned.

The market split is widening. New York City continues to outperform with strong rate-driven growth. San Francisco is finally showing life after a long recovery. Las Vegas, meanwhile, saw ADR drop 4.3 percent and RevPAR fall nearly 11 percent. Hawaiʻi landed somewhere in the middle: 2025 ended with modest statewide gains, with occupancy up slightly to 73.9 percent and RevPAR higher by 1.5 percent. Performance remained uneven across islands, as Oʻahu's RevPAR softened by 1.3 percent while Maui, the Island of Hawaiʻi, and Kauaʻi all saw gains, led by a 7.5 percent RevPAR jump on the Big Island.

Add some macro noise, and the picture gets shakier. A 43-day federal government shutdown in late 2025 wiped out more than $1 billion in hotel revenue. And with the 2026 World Cup approaching, even the talk of a potential boycott tied to geopolitical tensions is a reminder of how fragile international demand can be. So much for mega-events being a silver bullet, even after a FIFA “peace prize.”

New Logo, New Name, Same Synxis

As we reported earlier, Sabre Hospitality was carved out from Sabre Corporation and sold, temporarily living under the placeholder name “Hospitality Solutions.” Last week, it finally got its permanent rebrand: Aven Hospitality.

I’ll admit, I was quietly rooting for a return to something closer to its roots. SynXis, for all its quirks, is still one of the most recognizable core platforms in hotel tech. But alas, leave it to us clever marketing folks to decide the future is best signaled with a brand-new name that means… something aspirational?

New email domain, new community portal, renamed products, and a rebranded learning platform are all part of the Sabre separation. URLs stay the same, but plenty of back-end plumbing is getting reworked.

New name. New logo. Same mission. The real test isn’t the rebrand. It’s what they ship next. If you are a user of the company formerly known as Sabre Hospitality, some good information can be found here.

Digital marketing bumming you out?
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Digital marketing can be a headache, even the experts at Talk Agency agree.

But the topline revenue growth and bottom-line profit improvement you can get from it definitely do not suck, especially in a soft market.

The problem isn’t your dislike for digital marketing. Its lack of a clear, easy-to-implement strategy and a closed tracking loop that clearly shows MoM improvement, as well as what is and isn’t working. 

Talk Agency is ready to roll up their sleeves and dig into your business to build an action plan that delivers results, not promises.

Book your free digital marketing clarity workshop with our founder, Cooper Jitts, to unlock new growth today. 

Industry Events

Help celebrate the relaunch of Hawaii.com
-Sponsored-

The team behind Hawaii.com is hosting an evening of food and cocktails to celebrate their recent relaunch. Learn more about their vision as they continue building a trusted platform for travelers and local partners.

Date: Thursday, February 26th Location: ‘Alohilani Resort Waikīkī Beach - SWELL Pool and Bar Time: 5:00–7:00 PM

Space is limited; if capacity is reached, you will be added to a waitlist and kept informed as the event approaches.

• PATA 2026 Annual Outlook & Economic Forecast Forum - February 6, 2026 (Oahu)

• HLTA 2026 Na Po‘e Pa‘ahana Awards – February 11, 2026 (Oahu)

• The Hospitality Show (AHLA and HHA) - February 12, 2026

Full list of 2026 Hawaiʻi Events 

*If you have industry events to share, please email me at Dan@hawaiihotelhui.com.

Spotlight on Hawai‘i Hospitality Opportunities

• Hotel Assistant Manager - Prince Waikiki (Honolulu)

• Director of Revenue Management - Renaissance Honolulu (Honolulu)

• Vice President, Operations The Americas - OUTRIGGER Hospitality Group (Honolulu)

• Area Marketing Manager - OUTRIGGER Hospitality Group (Kailua-Kona)

• Vice President, Hawaii Revenue Strategy - OUTRIGGER Hospitality Group (Honolulu)

*If you happen to have any job openings, let us know. We will be glad to include them in the newsletter, space permitting; send the job link to Dan@hawaiihotelhui.com.

The inbox was active this week, which is exactly what we want. This newsletter is meant to be a conversation, not a monologue, and the Hui definitely had plenty to say, especially regarding the shift in tourism messaging.

We love the feedback, whether it’s a pat on the back or a reality check. Here is what you had to say.

Praise from the Peanut Gallery

• “Loving your Hawaiʻi Hotel Hui emails! Mahalo nui for the insight and mana'o.”

• “Nice newsletter! I've just forwarded [to] brand partnerships.”

• “Good job on this newsletter. Very informative and great in sharing about NYC, Waikiki, and AI trends... Agree messaging is better, moving away from the teaching to what Hawaiʻi is.”

  • Editor’s Note: Mahalo for the forwards. It is the highest compliment we can get (and helps us keep the lights on).

The HTA / HVCB Messaging Debate

• “As for the messaging and Japan communications, I bet Malama did not encourage one Japanese visitor to come or return to Hawaiʻi.”

• “The message isn’t ‘finally right’... It’s right for the current time. It shifted to themes like Mālama in 2021 when the first wave of tourists was arriving post-pandemic. Many were coming in with the wrong mindset... People needed to be invited to experience Hawaiʻi from that mindset... Is it time for something new? Sure, but it doesn’t mean that wasn’t right five years ago.”

• “I wouldn’t say ‘the message is finally right’ because it might imply that the previous message was wrong, which, in my opinion, is not wrong. Maybe from a marketing perspective it was, but it was what Hawaiʻi needed at that time, especially Maui.”

On Development & Closures

• “Another iconic business closing [Paradise Cove]... soon only memories will remain of these institutions that shaped the experience for residents and visitors alike in the 1980s and 1990s.”

• “I am a bit concerned ... for sure it will affect Maui’s economy ... I used to work with a Real Estate developer on Maui with a mission to provide affordable homes... until they had to let us all go because we were not able to get the approval on the last proposed affordable housing subdivision. It’s not simple... it’s all quite complicated... so many things to consider...”

• “Maui seems a little bit busier… but it’s high season, so it’s usually busier… It’s hard to tell, but praying we are on our way to recovery.”

Agree? Disagree? Have a hot take on the "Green Fee" rollout? Fire back at Dan@hawaiihotelhui.com. We read every single one.

About Us

Hawaiʻi Hotel Hui was started by hotel industry veteran Dan Wacksman, CEO of Sassato, a Hawaiʻi-based consultancy that combines deep local expertise with a global perspective.

Our team brings decades of experience across operations, marketing, revenue, tech, and finance, all aimed at helping hotels and travel companies make smarter decisions and move faster. Whether you need additional expertise, extra horsepower, or just someone who thinks like you and moves things forward, we’ve got you. From local independents to global brands, we show up with a no-nonsense, results-focused mindset. To be blunt: we get sh*t done.

Recent projects include brand transitions, system selection (PMS, CRS, CMS — all the acronym soup), implementations, project management, feasibility studies, training, audits, and everything in between.

A lot of organizations deal with stretched teams, siloed processes, and messy tech stacks that quietly stall important work. We fix that. Happy to chat if this hits close to home.

Aloha!

Mahalo for being here, and welcome to this month’s Hawaiʻi Hotel Hui Insider.

Big mahalo to our quarterly title sponsor, Allana Buick & Bers. I’ll be honest, before we connected, I only had a rough idea of what they did. After learning more, it’s clear they’re focused on a problem most owners deal with, usually the hard way. In plain English, ABB helps hotels get ahead of mechanical and HVAC issues before they turn into expensive, guest-facing disasters. Their architects and engineers assess what’s actually broken, or about to be, then design and manage the fix. Less firefighting, more planning, fewer surprises.

This month, we’re covering Hawaiʻi’s friendlier tourism reset, a closer look at increased surveillance in Waikīkī, and whether the destination is quietly picking up a fourth “S”: Sun, Sand, Surf, and Surveillance. We also take a close look at Airbnb’s latest swing at the hotel business, which feels familiar, but this time it might be for real.

We often have a point of view with our stories, and we know not everyone will agree. That is why we welcome people to comment publicly on our posts on LinkedIn or send us feedback directly. Who knows, you might end up in our Anonymous Comments to the Editor section.

As a small gift to the Hui, we put together a short, no-fluff AI guide. It’s meant to help you stop rewriting SOPs from scratch, cut through bloated docs, and get something actually useful out of AI. Inside are the prompts and workflows we use to save time.

Do you know we have a website where you can find previous issues and other resources? Check us out at HawaiiHotelHui.com.

If this newsletter is useful to you, share it with someone who might appreciate it! The more perspectives we have, the better. 😉

New here? Join the hui below. It’s free.

Mahalo for sticking with us!

Let’s dive in.

Mahalo,

Dan Wacksman
Hawaiʻi Hotel Hui Insider Editor-in-Chief 😄

Heads in Beds, Hands in Cuffs

One of the more interesting parts of my hotel days was reading the daily security reports. Sometimes amusing, sometimes terrifying, always written in Pentagon-style. I still recall a line that appeared more than once: “Security assisted the individual to the ground for their safety.” Hotel security teams are a distinct breed. I was reminded of that at the recent Visitor Public Safety Conference, put on by HLTA earlier this month.

While I usually focus on heads in beds, not hands in cuffs, the range of topics was eye-opening, from natural disaster preparedness to assisting visitors who are victims of crime (if you’re not familiar with VASH, you should be). But the discussion that really stuck with me was surveillance.

The pitch around drones and security cameras was compelling. The idea is that in a dense, fast-moving environment, a drone could be on scene in roughly 45 seconds, capturing footage well before officers arrive. Layer that on top of calls for more fixed security cameras, more monitoring, and AI, and you start to see a broader shift taking shape. This isn’t just about one tool; it’s about building a much more visible, always-on security and surveillance environment.

I understand why this is attractive. Faster response times, better situational awareness, and safer outcomes for visitors, residents, and officers alike are all legitimate goals. Director Mike Lambert addressed privacy concerns directly, joking that he wasn’t interested in what you had for lunch. I believe him, and I don’t question the professionalism or intentions of the people currently tasked with using these tools. But the harder question isn’t about today’s intentions; it’s about tomorrow’s reach. As cameras, drones, and data collection expand, we should at least pause to ask whether the balance between safety and personal privacy is shifting, and if so, how far we’re comfortable letting it move.

Technology has a habit of moving faster than legislation, and rarely pauses to think through mission creep or unintended consequences. The definition of “appropriate use” slowly expands. More data is stored. More access is granted. While we may all agree with the current intent, that doesn’t mean we’ll always agree with how it’s used. I want safer streets and safer guests in Waikīkī. I’m just not sure I’m comfortable with a more pervasive surveillance environment becoming the price of admission.

The conversation gave me a small-kine chill down my spine.

We Finally Stop Lecturing and Start Selling

After years of "Mālama" and "Kuleana" messaging that occasionally felt like a mandatory homework assignment for visitors, the HTA and HVCB have pivoted with "Hawaiʻi Stays With You." While I am all about Mālama and Kuleana, the sentiment was often lost on visitors. The new campaign, developed by the HVCB, debuted at a Los Angeles Rams game on January 4th.

This campaign signals a move toward high-def imagery and 'Instagrammable' moments and feels less like teaching and more like inviting. It is a pragmatic shift acknowledging that while travelers want a transformational connection, most prefer to find it through swimming, hiking, and eating rather than planting taro. The challenge now is how to amplify this message on a limited budget.

Watch the video that launches the campaign here. What do you think?

NOTE: Since people are often confused by this, here’s a quick clarification. HTA is a state agency now housed within DBEDT and does not do destination marketing itself. That work is contracted out. For the U.S. market, marketing is handled by the Hawaiʻi Visitors and Convention Bureau (HVCB), a private nonprofit.

Locally Rooted Hospitality
-Sponsored-

MacNaughton Hospitality is a full-service owner and operator with a growing portfolio including Waikiki Malia, Lotus Honolulu, Hotel Renew, and Arden Waikiki. Rooted in the MacNaughton family legacy, the platform is built on long-term ownership and hands-on stewardship, prioritizing performance without losing sight of people or place.

Working closely with partners, the team delivers hospitality that is financially sound, operationally efficient, and culturally grounded. Rather than a one-size-fits-all model, they tailor deep expertise in asset management and operations to the unique character of each property. From brand development to daily execution, the focus remains clear: building resilient assets, empowered teams, and guest experiences that stand the test of time.

Airbnb and Hotels: We’ve Heard This Before. This Time Might Be Different.

Airbnb’s hotel ambitions are nothing new. The HotelTonight acquisition in 2019 was widely seen as the turning point, before the pandemic put everything on pause. Now the company is back at it, with a pilot program and senior talent in place. Call me cynical, but the timing doesn’t feel accidental. Short-term rental regulations are tightening across major cities, and Airbnb’s sellable inventory is shrinking.

In test markets like Madrid, Los Angeles, and New York, Airbnb is more aggressively contracting and presenting hotel inventory. The platform appears to be moving toward a more unified accommodations experience. In short-term-rental-starved New York, hotel listings now show up front and center alongside traditional Airbnb inventory.

Airbnb has quietly formalized hotels as a real vertical. Jesse Stein, previously focused on real estate, has taken on a newly created Head of Hotels role, signaling this is now an owned business line, not a side project. Add in Jim Alderman, former CEO of Radisson Hotel Group Americas, now working on hotel supply and growth.

The clearest signal, at least to me, is the hiring of Lou Zameryka, a friend to many in this industry and a loyal Hawaiʻi Hotel Hui subscriber 😁. Lou helped build Booking.com’s hotel business and announced just last week that he is putting aside his entrepreneurial pursuits to focus on growing Airbnb’s hotel business as their new Head of Global Hotels.

Layer in the hiring of CTO Ahmad Al-Dahle, formerly of Apple and Meta, and the AI angle sharpens. Beyond improving Airbnb’s core business, AI could help the company leapfrog the legacy systems that continue to slow hotel distribution.

Recent reports also suggest Airbnb is offering lower commission rates than Expedia and Booking and is not bidding against hotels on Google or metasearch, at least for now😉.

Good luck, Lou, and please keep those commissions low and the marketing organic.

Different Cities, Same Math: NYC vs. Hawai’i

I grew up in New York City. I haven’t lived there in decades, but I still follow the news, and lately some of the tourism headlines feel very familiar in Hawaiʻi.

New York City’s effective ban on most short-term rentals isn’t changing anytime soon. A City Council bill that would have loosened the rules never made it to a vote in 2025. Current rules still prohibit most entire-home/apartment rentals under 30 days. The stated goal is housing protection. The observable impact so far has been a steep drop in legal STR supply, fewer options for visitors, and upward pressure on hotel rates. There is still little evidence that the policy has materially increased long-term housing supply or lowered rents, though supporters would argue it is early or that the effects are difficult to isolate. Sound familiar?

Another Hawaiʻi-adjacent moment caught my eye, too: the recent sale of the land beneath the Lotte New York Palace. Affiliates of Lotte paid $490 million to buy roughly 35,700 square feet of Midtown Manhattan dirt, converting a long-term ground lease into full ownership. That pencils out to about $13,700 per square foot. I’ll admit it, I didn’t even realize leasehold was a thing in New York City. Apparently, it’s not common, but ground leases do exist, mostly tied to long-held commercial and hotel properties in Manhattan. Unfortunately, none of them trace back to the Lenape, who were famously on the wrong side of Manhattan’s original land deal.

Which immediately brought me back to Waikiki.

The land beneath the Royal Hawaiian was traded for $510 million and covers roughly 10.3 acres, or about 449,000 square feet, putting it at about $1,135 per square foot. In other words, Lotte land in NYC traded at 12X Royal Hawaiian Land.

In supply-constrained markets, STR policy will continue to be a debated issue. The long-term value, though, stays with the land.

New York City and Waikīkī don’t have much in common on paper, but scarcity has a way of producing similar results.

It’s time to go all-in on direct.
-Sponsored-

When destination resorts package with air, they can offer more competitive pricing, giving travelers another reason to book direct. Tambourine is helping hoteliers bring the convenience of "one-stop shopping" to hotel websites without handing the relationship (or margin) to an OTA.

• Create an OTA experience on your hotel site, smooth shopping, fewer clicks, less friction

• Offer a lower overall price through bundled air + stay

• Less than 5% cancellation on packaged bookings (because people commit when flights are involved)

The Passport Gap: Easy Out, Hard In.

Did you know there’s a report that ranks passports by how useful they actually are for traveling to other countries? It’s called the Henley Passport Index, and for 20 years, it has tracked the number of destinations to which passport holders can travel visa-free. Singapore tops the list with visa-free access to 192 destinations, while Afghanistan remains last with just 24.

The U.S. passport is still strong, with access to 179 countries. But on the other end, the United States allows just 46 nationalities to enter visa-free, ranking 78th globally for openness. That’s one of the widest gaps between outbound mobility and inbound access anywhere in the world.

Meanwhile, China has quietly moved in the opposite direction, adding visa-free access for more than 40 countries in the past two years and now allowing entry to 77 nationalities. Call it diplomacy, call it economics, or call it demand generation, but openness is increasingly being used as a competitive lever in global travel.

And while the U.S. has not reduced the number of Visa Waiver countries, as we’ve reported in previous issues, it has continued to layer on new requirements that make entry more onerous, even for travelers from Visa Waiver countries (see our December article). 

Want to dive deeper? Check out the full 2026 Henley Global Mobility Report at Henley & Partners.

The Netscape Moment: Is ChatGPT Losing the Room?

In the early 1990s, Netscape ruled the browser world until Microsoft bundled Internet Explorer and pulled the market out from under it. Are we starting to see something similar play out in generative AI?

OpenAI’s ChatGPT popularized the category and deserves credit for it. But for those of us using it daily for research, analysis, coding, and document creation, the experience is starting to feel worn. The tool still works, but it increasingly feels like an employee who needs constant supervision.

If I had to correct a human staff member as often as I find myself correcting ChatGPT lately, they would not have made it through probation. Between model drift, inconsistent outputs, and frequent re-prompting, some of the early magic has faded. Meanwhile, Google Gemini has quietly evolved. The interface is cleaner, and in many use cases, the results now feel on par with, or better than, the competition.

Like Microsoft in the 1990s, Google’s real advantage is distribution and integration. By embedding Gemini directly into tools many of us already live in, Gmail, Drive, Sheets, Docs, and Analytics, Google is building a moat that is hard to replicate. And unlike most of its competitors, Google can self-fund this rather than relying on perpetual fundraising and massive losses.

Two recent developments suggest this shift may be solidifying.

• First, Apple has confirmed that Google Gemini will be one of the model providers integrated into the next generation of Siri, expected in 2026. Read More.

• Second, Google recently introduced its Universal Commerce Protocol (UCP), partnering with Walmart, Shopify, and Target to enable purchasing directly inside Gemini. Read More.

None of this means OpenAI is finished. But if performance issues and user friction persist, history suggests early category leaders are not guaranteed to stay on top. Without meaningful improvements or deeper strategic partnerships, OpenAI risks ending up in the same tech graveyard as Netscape Navigator.

BTW- If you are interested in the Browser Wars, here is a fantastic podcast about it.

Free Resource: Making AI Work for You

Speaking of AI utility, we created a practical resource to help you get more out of these tools right now. We’ve compiled a straightforward, no-nonsense AI guide designed to streamline your workflow; whether that's generating SOPs from scratch or summarizing complex documentation. It includes the actual prompts and strategies we use internally to save time and cut through the noise.

Industry Events

• PATA 2026 Annual Outlook & Economic Forecast Forum - February 6, 2026 (Oahu)

• HLTA 2026 Na Po‘e Pa‘ahana Awards – February 11, 2026 (Oahu)

• The Hospitality Show (AHLA and HHA) - February 12, 2026

Full list of 2026 Hawaii Events 

*If you have industry events to share, please email me at dan@hawaiihotelhui.com.

Spotlight on Hawai‘i Hospitality Opportunities

• Vice President Operations, Outrigger (Honolulu)

• Regional Director of Marketing & E-commerce – ʻAlohilani Resort Waikīkī Beach (Honolulu)

• Area General Manager - Aqua Aston Maui Kaanapali Villas (Maui)

• Director, Social Media – OUTRIGGER Hospitality Group (Honolulu)

• Vice President, Sales and Marketing – Travel + Leisure Co. (Honolulu)

*If you happen to have any job openings, let us know. We will be glad to include them in the newsletter, space permitting; send the job link to dan@hawaiihotelhui.com.

A little lighter on feedback this time, but I’m still happy to get it, praise, complaints, corrections, all of it. We always appreciate hearing what’s landing, what’s not, and what’s making people uneasy.

Praise (We’ll take it!)

• “So good. Happy New Year and congrats!”

• “Insightful and thought-provoking. 🤔”

On AI, Borders, and the Welcome Mat

• “If my experience is representative of a generation age 50 or older, there will be social media accounts that have been dormant for years and where people don’t remember handles or passwords… Will people be denied entry when they don’t list an account and the AI review process kicks in? There is no way humans can review the amount of data.””

• “Overall, it will reduce the number of inbound tourists, for Hawaiʻi and for the USA overall.”

• “Wondering how accurate AI is in reviewing social media content in foreign languages and different alphabets…”

On the Green Fee and Real-World Impact

• “Probably will not see any impact on this so-called ‘green.’”

• “My home is turning more expensive and unaffordable.”

On Japan, Pricing, and What the Data Actually Says

• “Looking at the development of the USD to Yen exchange rate, from 109 in December 2019 to 155 in December 2025, it is actually surprising to see the Japanese visitor market having recovered as much as it did.”

• “Hawaiʻi has to realize that other countries have built competitive products in the last 20 years, which are easier to reach.”

• “The closing of DFS stores indicates that businesses are not having a very optimistic outlook.”

Agree? Disagree? Think we’re missing the plot entirely?
Fire back at dan@hawaiihotelhui.com, and your take might show up here next issue, anonymously.

About Us

Hawaiʻi Hotel Hui was started by hotel industry veteran Dan Wacksman, CEO of Sassato, a Hawaiʻi-based consultancy that combines deep local expertise with a global perspective.

Our team brings decades of experience across operations, marketing, revenue, tech, and finance, all aimed at helping hotels and travel companies make smarter decisions and move faster. Whether you need additional expertise, extra horsepower, or just someone who thinks like you and moves things forward, we’ve got you. From local independents to global brands, we show up with a no-nonsense, results-focused mindset. To be blunt: we get sh*t done.

Recent projects include brand transitions, system selection (PMS, CRS, CMS — all the acronym soup), implementations, project management, feasibility studies, training, audits, and everything in between.

A lot of organizations deal with stretched teams, siloed processes, and messy tech stacks that quietly stall important work. We fix that. Happy to chat if this hits close to home.

Aloha and Happy New Year!

Mahalo for the support, the forwards, the replies, and the feedback. We’re kicking off 2026 the same way we ended last year: no fluff, no PR spin, no nonsense. Just the stuff that actually matters in Hawaiʻi hotels and tourism, plus a generous side of opinion and the occasional side-eye.

Big mahalo to our sponsors, Allana Buick & Bers’ (ABB) Mechanical CAPEX Services, which help property owners stay ahead of aging HVAC and mechanical systems through strategic, data-driven capital planning. Their in-house architects and engineers deliver a turnkey solution, assessing needs, designing improvements, and managing projects, so your team can stay focused on operating the building.

In this issue, the Green Fee arrives, Hilo lands a mainland route, we revisit the Minatoya List and who Minatoya actually was, break down some asset-light math, introduce a new AI acronym, and much more!

If you’ve been finding these updates helpful (or at least entertaining), please share them with a colleague or friend. The more folks we bring in, the stronger this hui becomes.

Not on the list yet? Join the hui below. It’s free.

Thanks for sticking with us. The Hui’s just getting started!

Let’s dive in.

Mahalo,

Dan Wacksman
Hawaiʻi Hotel Hui Insider Editor-in-Chief 😄

The Green Fee Arrives. Accountability Pending.

As of January 1, 2026, Hawaiʻi’s Green Fee is officially live, increasing the state TAT rate by 0.75 percentage points, from 10.25% to 11%. Hotels and vacation rentals are collecting, while the cruise ship tax is on hold after the Ninth Circuit Court temporarily blocked enforcement during the appeal.

For hotels, this effectively raises the cost of every stay and puts operators back in the familiar position of explaining tax policy at checkout, right alongside everyone’s favorite - resort fees, don’t get me started. BTW- Did you know resort fees get taxed also 🤦‍♂️.

The idea is well-intentioned: approximately $100 million a year for climate resilience, conservation, and “sustainable tourism,” guided by a new advisory council. The process is what’s concerning. The money flows through the general fund, and allocation requires legislative approval. Project-by-project details are still TBD, and allocations will be decided later through the recommendation budget process. What could go wrong?

We’ve seen this movie before with the TAT, which started as an earmarked fund for specific use, until it wasn’t. Without named projects, real dollar commitments, and hard guardrails, we are skeptical that the Green Fee won’t be redirected to uses beyond its stated intent.

So how do guests see these (and other) fees? Here’s an actual rate display from an Oʻahu hotel. No HHH commentary needed. 😲

Hawaiʻi Tops On-Time Flights List. In Other News: The Ocean Is Wet.

I always get a chuckle when Hawaiʻi is ranked the best state for on-time flights. As Guy Hagi says, we have the best weather on the planet. No snowstorms, rare major weather events, and most long-haul flights only operate once a day. Once the plane gets here, it usually parks overnight and behaves itself.

The study found just 12.7% of flights to, from, and within Hawaiʻi were delayed or canceled between July 2024 and June 2025, best in the nation. Weather aside, that kind of consistency still takes coordination, so kudos to the airport teams and airline ops for keeping things moving. For contrast, the worst airport in the study was Orlando International, where a brutal 32.4% of flights were delayed or canceled. Turns out a lot of people may leave the “Happiest Place on Earth” only to finish their vacation somewhere far less cheerful. 😉

Read More

New Visitors or Uncles and Aunties on their way to the California Hotel?

In other airline-related news, Southwest is giving Hilo its first nonstop to/from the continental U.S. in more than three years, launching Las Vegas to Hilo service on August 6, three times a week. Hilo hasn’t had a direct mainland flight since United ended its LAX service in early 2023, so this is a meaningful win for the Hilo side. That said, I have a feeling this route may see more locals in slippahs and board shorts trying their luck in Vegas than sun-starved tourists filling up Hilo hotels.

It’s time to go all-in on direct.
-Sponsored-

When destination resorts package with air, they can offer more competitive pricing, giving travelers another reason to book direct. Tambourine is helping hoteliers bring the convenience of "one-stop shopping" to hotel websites without handing the relationship (or margin) to an OTA.

• Create an OTA experience on your hotel site, smooth shopping, fewer clicks, less friction

• Offer a lower overall price through bundled air + stay

• Less than 5% cancellation on packaged bookings (because people commit when flights are involved)

Who Was Minatoya, and Why Does It Matter?

Last issue’s Bill 9 discussion (Maui County’s attempt to roll back certain legacy short-term rental rights) got me thinking about something basic but important: who exactly was Minatoya, and why is his list so important? 

The Minatoya List traces back to Richard Minatoya, a former Maui County deputy corporation counsel. In the early 2000s, his legal opinion, later upheld by the Hawaiʻi Supreme Court, allowed vacation rentals that were legally operating before zoning changes to continue as lawful, nonconforming uses. In short, the county tried to shut them down, lost in court, and the Minatoya List was born.

That ruling is the backbone of today’s issue; the list covers thousands (~6,000) of condominium units whose short-term rental use was explicitly protected by the courts. 

Minatoya himself passed away in 2018, but his legal legacy is very much alive. That’s why Bill 9 is different from past regulatory battles, as this is an attempt to unwind court-recognized property rights through legislation.

And those once “quiet conversations” about carve-outs are not so quiet anymore. Proposals circulating at the county level could exempt as many as 4,500 units from Bill 9’s reach (nearly 70% of the list!).  While Bill 9 has passed, clearly, nothing is settled, and the first court cases have already been filed.

Just when he thought he was out…

In what is probably the shortest retirement since Tom Brady, Dave Erdman is back. The founder and longtime CEO of PacRim Marketing Group, who sold the company to Vector in 2017 and stayed on to run it through the pandemic, and years of growth before moving into an advisory role and stepping down last year, has been named interim president and CEO of the Retail Merchants of Hawaiʻi, effective January 7. 

Given his Japan ties, we offered an otsukaresama deshita not long ago. That didn’t last long. So I guess now we are we have to continue the trend and say Okaerinasai, Dave.

Paradise Cove Closes. Making Room for Dukes and Mixed Feelings.

Editor-in-Chief Dan and family, including future Hawaiʻi Hotel Hui Project Manager Dylan enjoying his beverage.

After more than 40 years in Ko Olina, Paradise Cove Lū‘au is officially closing. The site is being cleared for redevelopment with plans for a new cultural and entertainment complex called Waianiani at the Cove. 

Before it’s gone for good, Paradise Cove is auctioning off just about everything. Tiki statues, canoes, furniture, golf carts, and more. A true end-of-an-era fire sale.

Duke’s at the Cove will anchor the new project. I love Duke’s and Hula Pie on the west side is winner. No argument there. But I still can’t help feeling a little nostalgic. It was kitschy, sure, but in a good way. It knew exactly what it was, and the location couldn’t have been better. It delivered memories, not just a show. Here’s hoping whatever replaces it remembers that part matters too.

Hotel Performance

Hotel performance data will be published in the first issue of each month.

Click here for the full DBEDT breakdown: Seats, stays, and then some.

Hyatt, Playa, and the Asset-Light Playbook

Hyatt acquired Playa Hotels & Resorts in early 2025 for $2.6 billion, then quickly sold most of the underlying real estate. The $2 billion sale of 14 resort assets to a KSL Capital Partners–backed group closed last week, with Hyatt retaining the long-term management contracts. If KSL sounds familiar, it should. The firm owns Outrigger Resorts and Hotels, the Sheraton Kauaʻi Coconut Beach Resort, and a long list of other properties worldwide.

In other words, Hyatt no longer owns the buildings, but it still runs the hotels, controls the brands, and collects the fees.

This is where it gets interesting.
Ownership vs. management, asset-light math, and why Hyatt walks away smiling.
→ Continue reading

Local Ownership. Long-Term Stewardship.
-Sponsored-

MacNaughton Hospitality is a locally owned and operated Hawaiʻi hospitality group built on relationships between people, places, and the communities it serves. The team owns and manages a growing portfolio of award-winning hotels and dining experiences, guided by the same stewardship and attention to detail that has defined MacNaughton’s work across the islands, from Park Lane Ala Moana to thoughtfully developed neighborhood retail.

Their approach is hands-on and grounded in respect for local culture. They believe hospitality works best when it feels personal: guests feel invited in, teams feel supported, and properties are cared for with intention. Day to day and long term, the focus is simple: create places that are welcoming, well-run, and true to where they belong.

New York Times Story That Should Get the Industry’s Attention

There was a really interesting article in The New York Times last month, How Much More Can the U.S. Travel Industry Take?, that cut through the usual tourism chatter and surfaced some uncomfortable realities about where U.S. travel actually stands heading into 2026.

The headline takeaway is simple: international travel to the U.S. is going backward. Industry estimates cited by the Times project 4.5 million fewer foreign visits in 2025 compared with 2024, the first post-pandemic decline. Canada has led the pullback, with arrivals down nearly 26% year to date, followed by declines from Germany at almost 12%, France at 7%, and South Korea at roughly 6%.

That matters because international visitors punch above their weight. They stay longer, spend more, and last year still accounted for nearly $179 billion in U.S. travel spending. That figure is expected to fall by about $6 billion in 2025, even as domestic travel volumes remain strong. In other words, domestic demand is filling rooms, but it is not fully replacing lost international dollars.

And here’s the part worth paying attention to.
What’s driving the downturn, why the U.S. is the outlier globally, and why Hawaiʻi is extra exposed.
→ Continue reading

Another Acronym Enters the Chat: MCP

Just when you finally figured out what an API was, or let’s be honest, you just nodded along, it’s time for a new acronym.

If you haven’t heard of MCP yet, you probably will in 2026.

MCP stands for Model Context Protocol. The easiest way to think about it is this: APIs were built so systems could talk to each other. MCP is built so systems can talk to AI. In hotel distribution terms, it’s the plumbing that lets an AI agent see real data, live rates, availability, and rules, and eventually handle things like booking and customer service.

This isn’t a travel-only thing. MCP is popping up across finance, retail, and healthcare. Travel just happens to be a great use case because it’s data-heavy, highly transactional, and built on real-time pricing and availability, exactly the kind of environment AI agents thrive in.

I keep reading articles about how hotels need to start learning and building MCPs, but let’s be real. Most hotels don’t build technology. They rent it. That means MCP connections won’t be created by hotels; they’ll be created by vendors like PMS, CRS, and other platforms. 

Meanwhile, OTAs already have clean data, massive scale, and direct connections (MCPs) into the major AI models. AI companies want the easy button. Travel is just one vertical, and OTAs make it far easier to plug in once than to wire up thousands of individual hotels.

MCP gets pitched as a way for hotels to bypass intermediaries. Maybe someday. In the near term, it’s more likely to make the biggest pipes even bigger.

Glossary for our non-hotel tech geeks

• LLM – Large Language Model. The AI brains behind tools like ChatGPT, Claude, and Gemini.

• PMS – Property Management System. The system that runs your hotel day to day: rooms, guests, rates, folios, the works.

• CRS – Central Reservation System. Where inventory and rates are managed and pushed to distribution channels.

• CRM – Customer Relationship Management system. Guest profiles, history, preferences, and marketing data.

• API – Application Programming Interface. The thing that lets one piece of software talk to another without humans getting involved.

If you are interested in Hotel terminology, we have a glossary on our website. 

Industry Events

• Visitor Public Safety Conference - January 7, 2026 (Oahu)

• PATA 2026 Annual Outlook & Economic Forecast Forum - February 6, 2026 (Oahu)

• The Hospitality Show (AHLA and HHA) - February 12, 2026

*If you have industry events to share, please email me at dan@hawaiihotelhui.com.

Spotlight on Hawai‘i Hospitality Opportunities

• Managing Director – Hilton Hawaiian Village (Oʻahu)

• Area Director of Marketing – PM Hotel Group (Hybrid)

• Area Marketing Manager – OUTRIGGER Hospitality Group (Kailua-Kona)

*If you happen to have any job openings, let me know. I will be glad to include them in the newsletter; send the job link to dan@hawaiihotelhui.com.

Pluribus Is Weird. I’m in.

I’m not entirely sure how to describe Pluribus, which is probably why I like it. It’s eerie and unsettling in the same slow-burn, vaguely disorienting way as Severance. The plot drifts, the tone is strange, and it is oddly addictive. I can’t help but think that this is an allegory for AI. 

It comes from Vince Gilligan, the creator of Breaking Bad, which immediately brought credibility. You can feel that DNA: patient pacing, quiet menace, and the sense that small moments are setting up something darker. I don’t fully know where it’s going yet, but I’m in.

It’s on Apple TV, which means I now have another streaming subscription. This whole unbundling thing is really working out well for us! They are currently dropping one episode a week (very old school), so you might want to wait until the full season drops so you can binge (and then cancel your subscription ☺️.)

On the bright side, Chief of War, also on Apple TV, is already queued up next, so at least I’m getting my money’s worth.

A new year, and I am genuinely glad we get to keep this section going. It is still one of my favorite parts of the newsletter. Disagreements, corrections, praise, and the occasional well-placed jab are all welcome. At the very least, it confirms people are actually reading. Mahalo for that, Hui.

Praise (Always Appreciated)

• “Insightful Newsletter -- Kudos to you!”

• “Congrats on your successful launch of the newsletter, how very exciting for you and your growing team.”

Corrections Department (Mahalo, eagle eyes)
Our readers continue to prove two things: they know their Hawaiʻi hotels, and they check the math.

• We made the mistake of using a stock photo listed as Maui for our story on Bill 9. An eagle-eyed reader pointed out that this was actually the Kona Tiki Hotel in Kona, Hawai’i Island.

• Another eagle-eyed reader noted that our math was off on the Maui numbers, and they were correct! We said 23,600 for Hotel+VR, but the math didn’t add up, it should be 22,600. See the correction below. BTW- Regardless, the numbers are a bit squishy depending on what source you are using.

  • By the numbers (again)

    • Maui hotel rooms: ~9,600

    • Maui legal vacation rentals today: ~13,000

    • Total visitor Hotel + VR today: ~22,600

    • Vacation rentals targeted by Bill 9: ~6,000

    • Hotel and Vacation Rental accommodations after full implementation: ~16,600

    • What that means

      • Roughly a 26.5% percent reduction in Maui’s total Hotel + VR supply

      • Roughly a 40 -45 percent reduction in the vacation rental inventory

• BTW- You do know we make these errors to see who is reading, right?  All part of the master plan ;-) 

On Bill 9 and what comes next

• “While my emotions agree with the bill and the intent to make housing more affordable (aside from the fact whether this measure will actually accomplish it), the legal question will center on whether the government can restrict the use of property that was legal when purchased. Owners will claim that the government is using de facto eminent domain without just compensation. The issue will go through courts for years.”

2026 Economy Check: Flat Is the New Optimistic
In the last issue, we asked how you are feeling about the 2026 economy. Nobody is popping champagne.

• 40.9% expect a flat, grind-it-out year

• 27% see modest growth

• 18% are bracing for a downturn

• 14% are already assuming a rough year ahead
  

Not bullish, but not panicked either. Cautious realism feels about right.

Agentic AI, Doing Actual Things

• “It's close... I booked a Turo for 2 weeks in Orlando yesterday. About 90% done by ChatGPT 5.2 agent. It picked the ride. I had to log it into Turo & I had to confirm the payment (at the agent’s request).”

Agree? Disagree? Either way, mahalo for thinking, responding, and being part of the conversation. Hit reply or send yours to dan@hawaiihotelhui.com: you might end up here next year.

About Us

Hawaiʻi Hotel Hui was started by hotel industry veteran Dan Wacksman, CEO of Sassato, a Hawaiʻi-based consultancy that combines deep local expertise with a global perspective.

Our team brings decades of experience across operations, marketing, revenue, tech, and finance, all aimed at helping hotels and travel companies make smarter decisions and move faster. Whether you need additional expertise, extra horsepower, or just someone who thinks like you and moves things forward, we’ve got you. From local independents to global brands, we show up with a no-nonsense, results-focused mindset. To be blunt: we get sh*t done.

Recent projects include brand transitions, system selection (PMS, CRS, CMS — all the acronym soup), implementations, project management, feasibility studies, training, audits, and everything in between.

A lot of organizations deal with stretched teams, siloed processes, and messy tech stacks that quietly stall important work. We fix that. Happy to chat if this hits close to home.

Aloha {{first name |}}!

In January, I made a deal with myself: publish one Hawaiʻi Hotel Hui Insider every month for the entire year. Twelve issues. No excuses.

I did not keep that commitment.

Because we didn’t publish 12. We published 16!

Somewhere between Issue 1 and Issue 6, a few thousand of you showed up. Engagement levels most publishers rarely see followed, the feedback was incredible, and companies started asking how they could sponsor (definitely not on our bingo card). We had to upgrade the tech, hire Dylan, learn a lot about newsletters the hard way, and figure out sponsorships without making it feel like a billboard. It’s been a blast.

But the most meaningful part has been the community that formed around it.

We want to thank our community, our Hui, for their continued support throughout the process. We’re looking forward to putting out more honest, useful, occasionally opinionated content in 2026 and seeing what else grows out of this along the way.

None of this would have been possible without you. So Mahalo, Mahalo, Mahalo.

We also want to wish you all an amazing holiday season and a fantastic New Year!

But wait…there’s more… we still have one more issue for you before the year ends. In this issue, we’re digging into why Waikīkī’s shoreline is starting to feel uncomfortably close; the confusing economic headlines (up, down, or panic mode); how the U.S. keeps adding friction for international travelers; and why AI search is quietly reshaping who shows up in the booking funnel. And more.

Before we dive in, a big mahalo to this issue’s sponsor, Lights On, our local hotel marketing and revenue experts, and the team that built the new Hawaiʻi Hotel Hui website. Lights On understands that marketing and revenue management only work when they work together. Their integrated approach helps hotels drive direct bookings through modern channels like AI search, optimize ADR through seasonal shifts, and navigate Hawaiʻi’s uniquely complex market without operating in silos.

Not on the list yet? You can join the hui below, no spam, no cost, just real talk.

Thanks for sticking with us. The Hui’s just getting started!

Let’s dive in.

Mahalo,

Dan Wacksman
Hawaiʻi Hotel Hui Insider Editor-in-Chief 😄

Maui’s Bill 9 Promises Homes for Locals, Critics Predict Economic Apocalypse

We first flagged Bill 9 in an earlier issue as a potential game changer for Maui’s housing and tourism mix. The bill, which seeks to phase out short-term vacation rentals in apartment-zoned districts affecting roughly 6,000 grandfathered units, cleared the County Council on second and final reading yesterday, December 15, by a 5–3 vote.

The bill now advances to Mayor Bissen, who introduced it in May 2024 and has said he will sign it. As passed, Bill 9 phases out these short-term rentals, with implementation beginning January 1, 2029, in West Maui and January 1, 2031, for the rest of the county. The delayed rollout is intended to give owners time to transition their properties.

Supporters continue to frame Bill 9 as a long-overdue housing correction. Opponents point to the administration’s own financial analysis and UHERO modeling, which suggest millions in losses in visitor spending, tax revenue, and jobs, at a time when Maui’s economy is still recovering.

The bill’s passage is unlikely to be the end of the story, with legal challenges expected and parallel discussions already underway about carving out certain properties from the phase-out through future zoning changes.

By the numbers

• Maui hotel rooms: ~9,600

• Maui legal vacation rentals today: ~13,000

• Total visitor Hotel + VR today: ~23,600

• Vacation rentals targeted by Bill 9: ~6,000

• Hotel and Vacation Rental accommodations after full implementation: ~17,600

What that means

• Roughly a 25 percent reduction in Maui’s total Hotel + VR accommodation supply

• Roughly a 40 -45 percent reduction in the vacation rental inventory

Data sources: UHERO, HTA 

One line from the debate captured the emotional core of the issue. As Council Member Keani Rawlins-Fernandez put it, “Profits are replaceable. Generational communities are not.”

Whether this creates housing for locals, reshapes the visitor economy, or gets rewritten in court remains an open question. This story is certainly not over.

Read More

Back on Oʻahu, the 90-day rule is still stuck. Nothing has changed since we reported back in August. A federal court has ruled it can’t be enforced until the city builds a process for legally existing rentals. That hasn’t happened, so 30-day rentals remain the standard in residential and apartment-zoned areas.

Big Slippahs to fill at Hilton Hawaiian Village

According to a recent Hawaii Hotel Alliance newsletter, Hilton is losing a major leader with the retirement of Debi Bishop, the Managing Director of Hilton Hawaiian Village. We didn’t know her personally, but her strong reputation across Hawaiʻi’s hotel community made it clear she set a high bar. Congratulations on an amazing career, and wishing Debi a fantastic retirement.

Now, Hilton is searching for a new Managing Director with proven large-scale resort experience, commercial sharpness, and the ability to lead a huge union workforce while staying grounded in Hawaiʻi’s culture and community. It’s one of the biggest roles in Hawaiʻi hospitality, and the next leader will be stepping into some very big slippahs. If you think you have what it takes, you can check out the job description here.

How The Kahala Hotel & Resort Achieved 106% Revenue Growth
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The Kahala Hotel & Resort just proved what's possible when hotels stop operating in silos. Working with Lights On, the luxury property achieved 106% direct revenue growth since 2023 through integrated marketing and revenue management.

The results? A 35.97x Google Ads ROAS → nearly double the typical industry benchmark of 10-20x. 89% direct revenue growth in year one, sustained with 9% growth in year two. Revenue per user up 81%. Exceptional performance across paid search, Facebook/Instagram, organic, and direct traffic.

Hawaiʻi-based with decades of hotel experience, Lights On knows what it takes to drive direct bookings while protecting ADR. Because the best marketing strategy means nothing if your revenue strategy isn't in sync.

Ready to stop leaving money on the table?

When the Waves Reach the Hotel Walls

Hightide at Outrigger Reef

A recent PBN article made me stop and think. It also brought to mind a few recent walks through Waikīkī, where watching waves lap directly against the sides of hotels felt less like a beachfront resort and more like standing on the deck of a cruise ship. In the PBN piece, attorney Norman Cheng noted that one trend popping up more often in Hawaiʻi real estate deals has nothing to do with interest rates or RevPAR. Sea level rise concerns are now impacting transactions for oceanfront assets.

This concern is not unique to Hawaiʻi. Coastal hotel markets around the world are grappling with similar questions, from rising insurance costs in parts of South Florida to tighter setback and retreat rules in Europe and island destinations that now factor long-term shoreline stability into underwriting.

What makes this more than a theoretical discussion is the growing reliance on intervention. Waikīkī’s last major beach replenishment wrapped up in 2021, when sand was dredged offshore and placed along Waikiki Beach to restore lost shoreline. The roughly three and a half million dollar project was funded through a public-private partnership between the state and Waikīkī hotels. That effort followed a similar effort in 2012; it is clear that Waikīkī’s beachfront now depends on recurring intervention rather than natural recovery.

You might recall that shoreline protection and beach replenishment were cited as potential uses for the recently approved Green Fee. So far, things have been relatively quiet on how those funds will actually be deployed, even as the need becomes more obvious. And this is not just a Waikīkī issue. Kā‘anapali, Kahana, and many other beaches continue to wrestle with erosion and beaches that are literally disappearing.

This isn’t climate modeling or long-term speculation. It is underwriting, capital planning, and real money. And it is beginning to influence how buyers value some of the world’s most desirable oceanfront hotel assets, Hawaiʻi very much included.

Growth, Flat, or Mild Recession? Pick Your Headline.

If you skim the headlines, Hawaiʻi’s economy looks like it is warming up. DBEDT just raised its 2025 growth forecast to 1.6 percent, visitor spending in October jumped seven percent, and Japanese arrivals were up sixteen percent year over year (though still about 45 percent below 2019). All seemingly good news.

Step away from the headlines and look at the data, and the picture becomes clearer. Year-to-date hotel performance is essentially flat statewide. Occupancy and ADR are largely flat, and RevPAR only looks healthy if you happen to own a luxury resort. Maui’s room revenue remains seventeen percent below 2022 levels, Oʻahu is down three percent, and midscale and upscale properties are taking the brunt of it.

Forecasts split. DBEDT sees modest growth, while UHERO is calling for a mild recession in 2026, driven by softer tourism, rising prices, and a weakening job market. Visitor arrivals are expected to dip again before conditions improve later next year.

So which version is real? Both? Hawaiʻi is getting a lift from higher spending and a slowly recovering Japan market, but the broader outlook still points to modest to flat growth, not a surge. Add rising insurance, utilities, shipping, and labor costs, loans that may need to be refinanced at higher rates, and it is easy to see why some are worried.

America Continues to Pull in the Welcome Mat

In previous issues, we’ve talked about the growing friction involved in visiting the United States. Higher fees. More paperwork. Longer waits. Stories about interrogations at entry points and even being refused entry. Now there’s a new one on the table. Hand over your social media.

A recent proposal from U.S. Customs and Border Protection (CPB) would require travelers from visa waiver countries like the U.K., France, Germany, and Japan to submit up to five years of social media history as part of their travel authorization. Not optional. The proposal would also expand the personal data required, including email addresses going back a decade and detailed family information. This proposal is now accepting pubic comment. Read the bill and learn how to comment here.

Here’s what international visitors are already facing, or soon may be:

In effect now:
• ESTA fee increased to $40, up from $21
• Land entry fee increased to $30, up from $6

Approved, rolling out soon:
• $100 surcharge for non-U.S. residents entering 11 major national parks

Passed but not yet implemented:
• $250 visa “integrity fee” for many non-visa-waiver travelers

Proposed:
• Mandatory disclosure of social media history for visa waiver travelers, as well as detailed biographical data (email addresses, family members, etc.)

U.S. Travel Association now projects a 6.3 percent decline in international visitation for 2025, the first drop since the pandemic. National Travel and Tourism Office data shows overseas arrivals have now fallen year over year for seven straight months, with November visitation still running at roughly 85 percent of pre-pandemic levels. Western Europe travel is down sharply, and Canada, historically the most reliable inbound market, continues to slide.

Visiting the U.S. is becoming more expensive, more complicated, and more intrusive, at a time when destinations around the world are competing aggressively for international travelers.

Which raises a simple question. If you were planning a vacation and another country asked for higher fees, more paperwork, and years of your online history, would you still want to go?

2026 Hawai’i Hotel Hui Predictions

As we close out 2026 and our first year of producing HHH, we couldn’t resist but to give our top 10 Predictions for 2026. It will be fun to look back at the end of 2026 to see how we did. If you have any predictions, please email them to us, and we will include them in the next issue! 

2026 prediction list

1. Flat is the new up, and holding ground is now considered a win for non-luxury properties.

2. Luxury holds, widening the gap between properties that can push rate and those that cannot.

3. Green Fee dollars become the most discussed pool of money, with very little actually allocated to their intended use.

4. Japan continues a slow recovery, but the old 2019 baseline is gone and should no longer be used as a comparison metric. 

5. Maui’s Bill 9 limiting short-term rentals is far from settled and likely headed for the courts.

6. AI hype cools, but AI search gets real as hotel visibility, click costs, and direct bookings are increasingly set by opaque, AI-driven ranking and ad systems, with Google regaining its crown.

7. Hotel debt, refinancing pressure, and slightly better terms than 2025 drive more deal activity, expect a few big ones!

8. HTA finally lands a permanent CEO and more funding, but remains well below peak levels, limiting how aggressive statewide marketing can be in 2026.

9. The Mandarin Oriental Ala Moana project gets scrapped.

10. The Lost City of Atlantis will still be lost with no movement and/or potential announcement of a different use for the land on the west side.

Holiday Cheer, Executive Edition

And finally, as you wrap up the year and wrap up your Christmas presents, you might not want to give one to the CEO. Reported hotel CEO compensation jumped again this year, rising from roughly $9.8 million to $11.9 million on average, driven largely by long-term incentives, while the average hospitality salary stalled just under $58,000. I included OTA CEOs as well, so you can see where your commission is going ;-).

1. Glenn Fogel, Booking Holdings: ~$44.8M

2. Anthony Capuano, Marriott International: ~$29M

3. Chris Nassetta, Hilton: ~$22M

4. Mark Hoplamazian, Hyatt: ~$18M

5. Geoff Ballotti, Wyndham Hotels & Resorts: ~$13–14M

6. Ariane Gorin, Expedia Group: ~$13–14M

7. Elie Malouf, IHG: ~$8–9M

8. Sébastien Bazin, Accor: ~$7–8M

Read More

Everyone Loves New Acronyms! And AI Just Added a Few More

Not that long ago, driving organic traffic was mostly about one thing: making sure your website was optimized for search (which mostly meant Google). We called it Search Engine Optimization (SEO).

Get the keywords right, clean up the site, earn some links, and hope you showed up on page one.

AI has quietly rewritten those rules.

Today, travelers aren’t just searching, they’re asking. Tools like Google’s AI results, ChatGPT, Perplexity, and Bing are answering questions directly. That shift has spawned a new batch of acronyms. You’ll hear GEO (Generative Engine Optimization), meaning whether your hotel shows up in an AI-generated response at all. You’ll hear AEO (Answer Engine Optimization), which is about how that response describes your hotel and whether it nudges someone toward booking.

These terms are very new and are still being defined and redefined as things evolve. The bottom line is simple: you want your hotel to show up in AI search, and you want it to show up in a positive, accurate way.

It’s no longer just about ranking well. It’s about whether the AI understands your property correctly or includes you at all. These systems pull from everything already out there: your website, OTAs, reviews, press coverage, online chatter, and so on. If your story is inconsistent, the AI fills in the blanks for you.

This is an emerging field, and anyone claiming to have a magic bullet is probably overselling it. What we do know right now is that these things help:

• Search for your hotel in AI tools and see how you’re described.

• Align descriptions, amenities, and positioning across your website and OTAs.

• Pay attention to reviews, press, and third-party content that shape perception.

• Create one clear version of your brand story and use it everywhere.

• Track AI-driven traffic separately. These guests tend to arrive closer to a decision.

And here’s the kicker: once you do show up and the searcher falls in love with your property, how will they actually book? Unless we’re very deliberate about what comes next, you can probably guess where that booking goes. And yes, that path has its own familiar three-letter acronym.

Industry Events

• Visitor Public Safety Conference - January 7, 2026 (Oahu)

• PATA 2026 Annual Outlook & Economic Forecast Forum - February 6, 2026 (Oahu)

*If you have industry events to share, please email me at dan@hawaiihotelhui.com.

Spotlight on Hawai‘i Hospitality Opportunities

• Managing Director – Hilton Hawaiian Village (Oahu)

• Director of Sales & Marketing – Kaimana Beach Hotel (Oahu)

• Reservations Manager – Rosewood (Big Island)

• Area Director of Sales – Hilton Hawaiian Village (Oahu)

• Sales Manager – Royal Lahaina Resort (Maui)

*If you happen to have any job openings, let me know. I will be glad to include them in the newsletter; send the job link to dan@hawaiihotelhui.com.

As we close out the year, it feels right to pause on this section for a moment.

When we launched Hawaiʻi Hotel Hui Insider, this wasn’t even part of the plan. After the first issue was released, emails started coming in with opinions. Pushback. Corrections. Praise. Strong disagreement. We quickly realized two things: people were reading, and whatever this was, it couldn’t stay just between us.

Flash forward 11 months, and this has become one of my favorite parts of the newsletter.

The original goal of HHH was never consensus. It was meaningful discourse. Whether we agree or disagree with what’s below is beside the point. What matters is that people are thinking critically, challenging assumptions, and engaging with ideas that impact our industry and Hawaiʻi more broadly. We’re not always going to land in the same place, and that’s okay. The important part is not shutting the conversation down.

With that in mind, here are a few year-end thoughts from the Hui.

Fun Stuff

• “I read the Don Don Donki in the tune of the song in my head. The Donki song is stuck in my head now… thank you. 😊”

  • Editor’s note: You’re welcome.

Praise

• “Mic drop for sure in this issue. Well done.”

• “I liked all the comments at the end from people. Good to know that people are paying attention.”

• “Just want to reiterate my thanks and appreciation for writing about basic truths and honest perspectives beyond the government-approved slop that doesn’t go through the sterilizing editorial processes of other ‘journalistic’ outfits.”

Strong Opinions (Not Mine!)

• “Lost in all the headlines about increased spend is the continued have and have not between luxury and everything else, with the ‘everything else’ down double digits and in desperate need for something positive… Airbnb enforcement (have we given up?), real marketing, some direction from HTA?”

• “The ‘Right Kind of Tourist’ doesn’t even sound good on a panel and is just stupid. We’re painting ourselves into a very narrow corner when the only successful kind of tourist is luxury, even though we aren’t really a luxury market.”

Reality Checks

• “I’ve often heard ‘don’t lower rates because we don’t want that kind of guest.’”

• “The most damage I’ve ever seen done to a room was by a famous pop star paying a really high rate… cigarettes on sofas, a crystal bowl through an 80-inch TV, and heels scratching wood floors.”

Constructive Criticism

• “Looking for the ‘right kid’ in school is laziness. In tourism, it’s also an attempt to sound smart without really saying anything.”

• “If you provide essentially the same experience as any other beach destination, you will never get the ‘right’ tourist. Differentiate the product and create a real sense of place.”

• “Becoming a playground for billionaires might not attract visitors who are mindful of the land, ocean, and local residents.”

Agree? Disagree? Either way, mahalo for thinking, responding, and being part of the conversation. Hit reply or send yours to dan@hawaiihotelhui.com: you might end up here next year.

About Us

Hawaiʻi Hotel Hui was started by hotel industry veteran Dan Wacksman, the CEO of Sassato, a Hawaiʻi-based consultancy that combines deep local expertise with a global perspective.

Our team brings decades of experience across operations, marketing, revenue, tech, and finance, all aimed at helping hotels and travel companies make smarter decisions and move faster. Whether you need additional expertise, extra horsepower, or just someone who thinks like you and moves things forward, we’ve got you. From local independents to global brands, we show up with a no-nonsense, results-focused mindset. To be blunt: we get sh*t done.

Recent projects include brand transitions, system selection (PMS, CRS, CMS — all the acronym soup), implementations, project management, feasibility studies, training, audits, and everything in between.

Aloha {{first name |}}!

Welcome to this month’s Hawaiʻi Hotel Hui Insider. We hope everyone had a fantastic Thanksgiving! 

A big mahalo to this issue's sponsor, Lights On, our local hotel marketing and revenue experts, who also built the new Hawaiʻi Hotel Hui website. They know hotels need marketing and revenue management working together, not in silos. Lights On's integrated strategies drive direct bookings through modern channels like AI search, optimize ADR through seasonal shifts, and provide strategic revenue guidance for hotels across the islands.

We just launched the new site and would love it if the Hui took a look. Kick the tires, test it out, break it if you can. Seriously. Let us know what works, what doesn’t, and what’s missing. Just hit reply and share your thoughts: HawaiiHotelHui.com.

Do you know we read and respond to every email we receive? Ok, this is not quite a herculean task, as we only receive a few each issue. But we love receiving them, and rest assured, we read and respond to them, so don’t be shy in giving us feedback

Here’s what we’re covering this issue: the messy truth behind “the right kind of tourist,” cruise lines outpacing hotels, plus: a long-stalled Kona parcel finally gets new life, Hopper quietly drifts toward the exit, and we separate agentic AI hype from reality.

Know someone in Hawaiʻi hospitality who should be reading this? Forward it their way. Sharing helps us grow the Hui!

Not on the list yet? You can join the hui below, no spam, no cost, just real talk.

Thanks for sticking with us. The Hui’s just getting started!

Let’s dive in.

Mahalo,

Dan Wacksman
Hawaiʻi Hotel Hui Insider Editor-in-Chief 😄

“The Right Kind of Tourist”

OK, we may get flak for this, but here goes…

When I lived in Hong Kong, we were touring schools for my kids. I vividly remember an admissions officer saying, with a straight face, “We only want the right kind of children.” I probably should’ve smiled politely and moved on. But I couldn’t help myself. I told him, “All children are the right kind of children,” and asked, “What exactly does a ‘wrong’ six-year-old look like?”

Shockingly, we didn’t get in.

But that phrase - “the right kind of child”- has stuck with me. And while it’s not quite the same, I get that same pit-in-the-stomach feeling every time someone in tourism talks about attracting “the right kind of tourist”, or whatever the buzzword of the month is: mindful, high-spending, low-impact, values-aligned, pre-screened by karma.

It’s one of those lines that sounds smart on a panel and looks good in a PowerPoint, but crumbles the second you try to define it. The truth is, we don’t get to custom-order tourists from a catalog. And when we start categorizing people like inventory, we’ve missed the point.

Instead of gatekeeping, we should be focused on managing the experience: educating visitors, investing in infrastructure, reinforcing local values, and supporting the communities that host them. That’s not about filtering people, it’s about raising the bar for how we host, and how we ask to be treated in return.

I get the intent behind phrases like “mindful” or “high-value” visitor; there’s real pressure to ease strain and protect what makes Hawaiʻi special. But when we start sorting people by worthiness, even subtly, we lose the plot.

Because just like with kids, maybe it’s not about finding the “right kind” of tourist, but creating the right kind of environment.

P.S. An article in SFGATE just last week highlighted how rising travel costs are already reshaping who visits Hawaiʻi. Maybe that’s a good thing, fewer people, more spending. But it does raise a question: at what point does price start to shape not just how many people come, but who feels welcome?

Read more here

New Role, Same Values

If you’ve worked in Hawaiʻi tourism for more than a minute, you know Kainoa Daines. Thoughtful, funny, and deeply rooted in place. So it makes sense that his next chapter puts values front and center.

After 14 years at the Hawaiʻi Visitors & Convention Bureau (HVCB), Kainoa is now Director of ESG & Culture at Kyo-ya and Marriott. As he said in his LinkedIn post, he’s trading six islands for six landmark hotels: Moana Surfrider, The Royal Hawaiian, Sheraton Waikīkī, Princess Kaiulani, Sheraton Maui, and the Palace Hotel in San Francisco.

He’ll be leading efforts across sustainability, governance, community impact, and cultural integrity, core areas that define how hospitality shows up for people and place.

Congrats, Kainoa. Looking forward to seeing how you shape what comes next and hoping we can still talk you into emceeing some industry events!

Note: If you’re wondering about the Marriott/Kyo-ya reference above, Kyo-ya, a Japanese company, owns the hotels listed above. They are branded and managed by Marriott.

The Future of Hotel Childcare Starts Here
-Featured Partner-

Are you ready for parents to fall in love with your hotel? Tutti Vacation's "Trust at First Sight" program is your fast pass to elevating the guest experience. Our babysitters arrive with a nanny camera to give parents total peace of mind. We offer transparent local pricing and low booking fees, no more overcharging guests.

With excellent customer service, easy booking, quick AI search tools, the ability for parents to choose their sitter, and a rapid-response button for last-minute care, Tutti Vacation Childcare is the leading, community-focused childcare solution. Rooted in Hawai‘i hospitality, Tutti blends genuine care with innovation. 

Partner with Tutti today and give your guests the very best!

New Life for an Old Eyesore in Kona

After sitting idle (and ugly) for years, a 1.75-acre lot in the heart of Kailua-Kona is finally getting a makeover. Hilton Grand Vacations just sold the parcel, once slated for a timeshare, to Maryland-based Baywood Hotels for $4.65M. Their plan? A $45M Residence Inn by Marriott, with 100 extended-stay rooms. That is a hefty $496K per key!

The site, next to Kona Reef Resort, had been stuck in permitting purgatory since 2023. With approvals finally in place, construction is now slated for 2027. Between this project, the Uncle Billy’s to Hampton Inn conversion, and the Pacific 19 refresh of the old Seaside Hotel, Kona is finally seeing some long-overdue investment.

Read More

Cruise Ships Are Winning. Hotels Should Take Notes.

I recently received a note from my friend and industry consulting legend, John Burns, pointing out something we’d rather not admit: the cruise industry is eating our lunch. While hotel occupancy has been flat or declining, cruise lines have surged ahead with aggressive marketing, sharp messaging, and a clear value prop. They’re filling ships through 2026 and already selling 2027. Meanwhile, we’re still blaming vacation rentals and other externalities.

Hotels and destinations would do well to take notes. This isn’t luck, it’s strategy. Cruise lines have stayed focused: consistent branding, big ad buys, and simple messaging that converts.

Meanwhile, Hawaii, as a destination, is still playing catch-up. As we noted last issue, many are practically begging the state and HTA for more marketing dollars, and that plea got louder last week. In a letter to the Governor, major wholesalers (Pleasant Holidays, Delta Vacations, ALG, Classic) warned that Hawaiʻi’s brand has “grown quiet” while other destinations outspend and outmaneuver us.

And in a somewhat related note, just as the cruise sector gains momentum, we’re also finding ways to dampen it. The state’s new “green fee” (which extends TAT to cruise passengers) is now facing a federal lawsuit, backed by the DOJ, arguing it violates maritime law. Cruise lines are also raising concerns over new emissions rules, saying the state lacks the infrastructure to comply.

It’s not that regulations don’t matter; they do. But while cruise lines move forward with a unified strategy and full ships, we’re sending mixed signals: underfunded marketing, muddled messaging (see: “the right tourists”), and policies that suggest we’re not sure we even want the business.

Without serious investment and alignment, we’re not just losing share, we’re handing it over.

Read more

Hotel Performance

Hotel performance data will be published in the first issue of each month.

Click here for the full DBEDT breakdown: Seats, stays, and then some.

Hopper: One Last Hop Before Exit?

Hopper was once the darling of travel tech. It launched as a mobile-first OTA aimed at younger travelers, blending slick design with gamified booking and “fintech” tools like price freeze and cancel-for-any-reason. They expanded into B2B with private-label travel portals and loyalty partnerships, powering companies like Capital One and Uber, while also selling their fintech tools to airlines and others.

But now, according to Skift, Capital One is acquiring the very software Hopper built to run its travel portal, and quietly hiring away Hopper’s hotel and engineering teams. For a company whose consumer app now accounts for just 10% of revenue, this seems more like an exit than a pivot.

Hopper’s app is still live, with 100 million+ downloads and millions of active users. But its future looks increasingly murky: no breakout growth in recent years, and now its biggest partner is pulling the tech (at least some of it) in-house. Capital One, like Chase (which bought cxLoyalty in 2020) and Amex, is moving past white-label deals and into owning the stack.

I’m no champion of OTAs, but it was nice to think there might be a viable foil to the Expedia/Booking duopoly. Hopper had a shot, but it doesn’t look like they’ll be the ones. Maybe Airbnb’s slow-played OTA ambitions will land better. Or will it all be replaced by Agentic AI? (See below)

Skift: Capital One Plans to Buy Hopper’s Travel Software and Hire Teams

It’s Baaack: Vacasa Gets Rewired

I’ve been out of the vacation rental platform weeds for a while, but a headline last week pulled me back in: Casago offloaded around 1,000 contracted VR units to Evolve. At first, I figured it was a pullback. Turns out, it’s a pivot. Those contracts came from Vacasa’s self-managed business, and Casago wants to focus on its core model: franchising.

You might have missed it, but earlier this year, Casago scooped up the smoldering remains of Vacasa for $130 million in cash. That’s gotta be a humbling moment for a company once valued at $4 billion (and even more humbling for their investors). But Casago didn’t buy it to keep the Vacasa machine running. They’re dismantling it and rebuilding it in their own image.

The Casago model is franchise-first. Local operators manage the homes, handle the guest experience, and maintain owner relationships. Casago provides the tech, marketing, training, and booking infrastructure. From a hotel perspective, it’s like a hotel franchise — Casago, or the “new” Vacasa, supplies the tools and brand. Local franchisees run the show.

A quick scan of the Casago and Vacasa websites shows just over 300 listings in Hawaiʻi. That’s a steep drop from Vacasa’s estimated peak of more than 1,100 listings statewide. But Casago is promoting franchise opportunities in Hawai’i on their website.

But will the math, math? Owner-manager splits these days often hover around 80/20 in favor of the property owner. That doesn’t leave much to be split between the franchisee and Casago/Vacasa. Then again, if the franchisees are lean, boots-on-the-ground operators with limited overhead, maybe it pencils out.

Do you think this model could work here? Should local VR management players be concerned?

P.S. Casago started as a small, family-run rental business in Mexico that Steve Schwab took over and grew into a national franchise brand managing over 40K properties. Now based in Scottsdale, Casago is privately held with significant institutional backing.

When Marketing and Revenue Work Together, Everything Changes
-Featured Partner-

That's especially true in softer markets like we're seeing now. Hotels that integrate marketing and revenue management protect ADR and maintain RevPAR while others struggle with siloed strategies.

Lights On unifies both disciplines to:

• Drive direct demand from AI search and digital channels while pricing strategically to maximize yield

• Optimize your channel mix so every booking strengthens your bottom line, not just fills rooms

• Navigate shoulder seasons and compression with campaigns and pricing that work in sync

Hawaiʻi-based with decades of combined hotel experience, Lights On knows what it takes to win in this market.

Ready to stop operating in silos?

Brand USA Funding Might Finally Catch a Break

Back in June, we flagged that federal funding for Brand USA had been slashed from $100 million to $20 million, and this is right before the U.S. is set to host the World Cup, America’s 250th, and the 2028 Olympics.

Now, a bipartisan group in Congress is trying to fix it. The VISIT USA Act would fully restore funding for fiscal years 2026 and 2027 using surplus visa fee revenue (not taxpayer dollars). The bill has support from both parties, multiple states, and a tourism industry that knows global demand doesn’t generate itself. Right now, the U.S. is coming across as unwelcoming: confusing entry rules, rising fees, increased border scrutiny, and even worse. If we want to stay competitive, we need to actively counter that perception and make it easier for international visitors to choose us.

Agentic Booking Is Not Here. But the Claims Are.

If your LinkedIn feed looks anything like mine, you’ve probably seen the headline: “Agentic booking is here.” It usually tops a press release or breathless post claiming that AI can now plan your trip, book it for you, and in the process, wipe out all your direct bookings, no clicks, no effort, just doom.

Except, it can’t. Not yet.

Real agentic booking means the AI actually makes the purchase, selects the room, enters your info, and charges your card. What we’re seeing instead (at best) is assisted booking: AI narrows your choices, maybe pre-fills a form, but the process for the most part is still old school internet shopping.

Google recently confirmed it’s developing an agentic hotel and flight tool inside AI Mode. They’re working with OTAs like Booking and Expedia, and the large brands like Marriott and IHG. But even Google admits this is early-stage stuff.

Google says it’ll be an “open ecosystem” with no preference for OTAs vs. direct (we’ll see), and CEO Sundar Pichai says full agentic capability is likely “within 12 months.” Translation: this is roadmap material, not real-world functionality.

So yes, agentic booking is coming, and yes, you should be making sure your hotels are findable on AI platforms and paying attention to how this evolves. But let’s not confuse roadmap slides with reality. Until AI can actually book a room while you’re in a meeting, the headline isn’t “Agentic Booking Is Here.” It’s: Agentic Booking Isn’t Here. Yet.

Industry Events

HSMAI Holiday Ho’olaule’a - December 11, 2025

Celebrate the spirit of the season with HSMAI Hawai‘i at their Holiday Ho’olaule’a, an evening dedicated to connection, community, and a look back at a fantastic year together. We invite you to join us for a festive night filled with camaraderie, cheer, and plenty of aloha.

• PATA Hawai‘i & TTRA Hawai‘i 2025 Industry Holiday Breakfast - December 5, 2025 (Honolulu)

• Maui Hotel & Lodging Association, Winter Mixer with Lahaina Brewery - December 10, 2025 (Lahaina)

*If you have industry events to share, please email me at dan@hawaiihotelhui.com.

Spotlight on Hawai‘i Hospitality Opportunities

• Director of Sales & Marketing – Kaimana Beach Hotel (Oahu)

• Reservations Manager – Rosewood (Big Island)

• Area Director of Sales – Hilton Hawaiian Village (Oahu)

• Marketing Manager – Alohilani Resort Waikiki Beach (Oahu)

• Sales Manager – Royal Lahaina Resort (Maui)

• Director of Sales – Royal Lahaina Resort (Maui)

*If you happen to have any job openings, let me know. I will be glad to include them in the newsletter; send the job link to dan@hawaiihotelhui.com.

You Don’t Need a Passport To Go To Kapolei

It’s been a while since I had an entertainment tip. Not for lack of trying. I’ve watched plenty of plane movies, but nothing was worth recommending. Until now.

My wife and I decided to break out of our usual loop in town and head west to Kapolei. And contrary to rumor, you do not need your passport when you exit H1. We made a day of it with a stop at the new Don Don Donki, a little shopping, dinner, and a movie. We caught Rental Family, starring Brendan Fraser.

Fraser plays an out-of-work actor in Tokyo who takes a gig pretending to be people’s family members. It’s based on a real service in Japan, and the movie leans into that bizarre-but-believable space with a lot of heart. The cinematography is fantastic, the supporting cast is outstanding, and as someone who speaks Japanese, it was refreshing to hear natural dialogue from actual Japanese actors, many of whom are stars in Japan. Fraser’s performance is fantastic and believable, and he even does a solid job with the Japanese. (The movie is mostly in English, with occasional Japanese and subtitles.)

The movie walks the line between drama and comedy, enough to be emotional and funny without tipping into sentimentality or slapstick. It doesn’t try to solve the big questions, but it sits with them. And more importantly, it leaves you feeling.

BTW – While Rental Family might make you tear up a bit, if you’re looking for full-blown waterworks, watch Brendan Fraser’s Oscar-winning performance in The Whale. Just... maybe not on a plane. Let’s just say my seatmate was less than thrilled with the grown man quietly losing it at 35,000 feet.

I always say I’ll cut this section if no one writes in... and yet, every month, the inbox proves otherwise. Mahalo for the notes, praise, gripes, and daydreams; they keep this project sharp!

🔥 Praise, with a Kick

• “I love your acerbic flair in weighing in on the hot topics of our industry… You say things that most people think but hold their tongue.” Editor’s Note: I’d say clever not acerbic.. tomato, tomahato, I guess 🤣.

• “Another riveting issue!”

• “Mahalo… you get a great open rate cuz we love ya!”

• “My boss and I love your page. And the tea LOL and the truths!”

🧠 Observations Worth Chewing On

• “We plan on visiting Maui in January 2026, but we are done after this year. You guys win—tired of being taxed—not feeling the Aloha spirit.”

• “From what I hear in the SoCal leisure market, Hawaiʻi prices are among the highest in their history… just saying.”

• “Been warning about this for months. I suspect the state government’s low spending on advertising is partly to blame… High prices and a waning, over-commercialized Spirit of Aloha are also contributing… January’s minimum wage hike won’t help any.”

• “Sure would be nice to have more affordable hotel rooms just steps away from the Hawaiʻi Convention Center. Throw in some parking, additional meeting space, and a pedestrian skybridge to HCC (sorry, just daydreaming over here!)”

As always, I’ve kept comments anonymous and only trimmed for length. Don’t agree? Have something to add? Hit reply or send yours to dan@hawaiihotelhui.com: you might end up here next month.

About Us

Hawaiʻi Hotel Hui was started by hotel industry veteran Dan Wacksman, the CEO of Sassato, a Hawaiʻi-based consultancy that combines deep local expertise with a global perspective.

Our team brings decades of experience across operations, marketing, revenue, tech, and finance, all aimed at helping hotels and travel companies make smarter decisions and move faster. Whether you need additional expertise, extra horsepower, or just someone who thinks like you and moves things forward, we’ve got you. From local independents to global brands, we show up with a no-nonsense, results-focused mindset. To be blunt: we get sh*t done.

Recent projects include brand transitions, system selection (PMS, CRS, CMS — all the acronym soup), implementations, project management, feasibility studies, training, audits, and everything in between.

Aloha {{first name |}}!

Welcome to this month’s Hawaiʻi Hotel Hui Insider.

First, a big mahalo to this issue’s sponsor, Tambourine, the hotel marketing tech pros behind some of the industry’s cleanest, sharpest websites. From full-service marketing to their new hotel-and-air booking engine, they’re helping hotels rethink digital from top to bottom.

In this issue: KS cashes out of Waikīkī’s most iconic ʻāina. Debt bubbles up beneath the surface on Oʻahu and Maui. Sonder flames out. TripAdvisor fumbles again. And Google’s cracking down on meta pricing shenanigans.

BTW- Our last issue pulled over a 60% open rate. That’s practically unheard of! If you’re reading this (and I think you are), and you’re enjoying it, please spread the joy and pass it along to your friends and colleagues.

The Hui doesn’t grow through algorithms or ads. It grows because you forward, share, and talk story. Mahalo for that.

Not on the list yet? You can join the hui below, no spam, no cost, just real talk.

Thanks for sticking with us. The Hui’s just getting started!

Let’s dive in.

Mahalo,

Dan Wacksman
Hawaiʻi Hotel Hui Insider Editor-in-Chief 😄

Crown Jewel, Sold. Legacy, TBD.

We’ve covered a few big land deals recently, but this one hit different. Kamehameha Schools (KS) has sold the land beneath the Royal Hawaiian Hotel, arguably the most iconic piece of real estate in Waikīki. The 10.3 acres of oceanfront land was sold to Japan-based Daisho Co. for $510 million. The hotel’s still operated by Kyo-ya under a long-term lease (locked in until 2076), but the underlying ʻāina has changed hands. Compare this to the recent KS sale of Hualālai land of $400 million for 31 acres.  

KS says the deal aligns with their 2030 strategic plan and helps them better manage their portfolio. I get it: a pile of cash can fund scholarships, infrastructure, be invested in higher-yielding vehicles, and cover liabilities. But still, this one surprised me. Land is permanent. Cash is transitory. The Royal Hawaiian is more than a hotel; it sits on land once home to the aliʻi with deep history.  

It’s also worth noting that the sale comes on the heels of some heavy financial and legal headwinds for KS, including an $872 million settlement tied to the 2023 Maui wildfires and a new federal lawsuit challenging its admissions policy.

According to KS, Daisho understands the significance of the land and intends to honor it, but let’s be honest, intentions are nice, but ownership is power. Daisho is a real estate investment and development firm, headquartered in Fukuoka with properties across the Asia-Pacific, but this is its first commercial acquisition in Hawaiʻi. 

I’m not usually shocked. This one shocked me.

Read More

Beach Front Waikīkī

Did you know there are only nine truly beachfront hotels in Waikīkī, where you can step outside the hotel and your toes are in the sand (or sometimes the water, thanks to erosion)? Here is the list, inorder, from Ewa to Diamond Head.

• Hilton Hawaiian Village – Fee Simple (Park Hotels & Resorts)

• Hale Koa – Fee Simple (Military Hotel - Federal Government)

• Outrigger Reef – Fee Simple (KSL Capital)

• Halekulani – Both: 1/6 leasehold (Robinson Trust); 5/6 fee simple (Mitsui Fudosan)

• Sheraton Waikīkī – Both: 1/4 leasehold (Robinson Trust); 3/4 fee simple (Kyo-ya)

• The Royal Hawaiian – Leasehold (Kamehameha Schools, soon to be Daisho)

• Outrigger Waikīkī – Leasehold (Queen Emma)

• Moana Surfrider – Fee Simple (Kyo-ya)

• Kaimana Beach Hotel – Fee Simple (BlackSand Capital and Tsukada Global)

Mahalo to our friends at Powell & Aucello for helping us unravel this, they track who owns what, and what’s really going on with Hawaii Hotels.

Revenue Strategy Only Matters if It Moves NOI - Everything Else Is Noise
-Featured Partner-

Owners don’t measure performance in rate changes - they measure it in margin, flow-through, and long-term value. And in Hawai‘i, consistent demand can hide the gaps that matter most for NOI. These are the levers that actually shift profitability for hotels:

1. Understand demand quality, not just pace.
Hawai‘i hotels often fill with the wrong mix because pace masks demand quality. Understanding which segments deliver true flow-through (not just revenue) is the difference between running busy and running profitable.  

2. Know your true cost of acquisition.
Contribution shifts once you factor in commissions, loyalty costs, rebates, and upsell potential. In Hawai‘i’s high-cost environment, misjudging channel cost erodes margin faster than a pricing mistake.

3. Prioritize demand that strengthens the asset.
The most valuable guests aren’t just the highest-rated; they’re the ones who retain, spend more, and cost less to acquire. Long-term value beats short-term occupancy spikes.

Debt Surfacing Like an Iceberg

A person in the know recently pinged me with a cryptic heads-up: “Start watching the debt at a lot of the Oʻahu and Maui hotels.” No details, no follow-up, just a subtle, ominous message. I felt like Woodward and Bernstein in the garage talking to Deep Throat. 

Here’s the subtext: A chunk of hotels, especially those that refi’d during the easy-money years (think 2020–2022), are now staring down maturities in a higher-rate world. Combine that with Maui’s sluggish recovery and softening international demand, and you’ve got properties where the math may no longer work. Even on Oʻahu, RevPAR gains are being chipped away by higher operating costs, rising insurance, and taxes that are not going down.

We’ve seen signs. The Fairmont Orchid just locked a $136M refi mid-reno, and the Grand Wailea pulled a $1B refi. Meanwhile, smaller Waikīkī hotels are quietly hitting the market, fee simple and unencumbered, aka “buy now, bring your own rescue plan.”

Keep an eye on loan maturities, capital calls, and ownership changes. Distress won’t scream, it’ll whisper, just like my source.

Is Hawaiʻi Tourism Sliding Into a Slow Burn?

Panelists Jerry Gibson, Danieal Bernard, and Jim Bramer felt they were seeing some “green shoots” for 2026.

After a sluggish summer and soft fall, Hawaiʻi’s visitor economy is flashing yellow. Arrivals dropped for three straight months (down 4.4% in July, 2.6% in August, 2.5% in September), and operators are reacting: cutting hours and forecasting layoffs.

Visitor spending is up. But it’s not enough to offset rising costs or weaker demand. UHERO reports stalled job growth and contraction in tourism-driven sectors. Some industry leaders say this is the worst economic-driven downturn since 2008.

Meanwhile, Expedia just posted stellar Q3 gains, driven by, among other things, U.S. travel demand. So why isn’t Hawaiʻi feeling the lift?

The lack of a statewide marketing strategy doesn’t help. HTA’s plans remain in limbo, the budget’s been cut, and the convention center closure looms. Japan’s comeback is slow, and Canadians are skipping U.S. trips altogether.

At the Aloha AHICE conference earlier this month, some speakers expressed cautious optimism that 2026 might bring relief once the market adjusts to a new administration and economic jitters settle. The expression used was “we are starting to see green shoots.” We hope they are right. But hope is not a strategy.

The message I keep hearing at industry events and in discussions with Hawaii hotel and toursim leaders, is that Hawai‘i is being outspent and outmarketed. Competing destinations are louder, clearer, and more aggressive. Meanwhile, we are sending mixed signals. Some visitors are wondering if they are even welcome. It is time to fix the optics and the outreach.

Springboard New Marketing Head

We mentioned in the June issue that Jason Pirock left his role as VP of Marketing at Springboard Hospitality to take on the global brand gig at Outrigger. That left a high-profile seat open, and now it’s been filled.

Eve Tronson, a longtime industry friend, has stepped into the role as VP of Marketing at Springboard, which, as you know from past issues, is now part of Hotel Equities. Eve will lead brand, digital, CRM, and field marketing strategy across the company’s portfolio of lifestyle and independent hotels, with over 50 properties, including 12 in Hawaiʻi.

Eve brings deep hospitality experience, including senior leadership roles at Viceroy Hotels & Resorts. Aloha and welcome, Eve. We look forward to seeing you in the islands.

Sonder Went Bust. Marriott Went Missing

We Were Shocked by the Royal Hawaiian Deal. Sonder Collapse? Not So Much.

Once hyped as the future of hospitality, Sonder took on long-term leases to operate apartment-style hotel rooms, that is, until the cash ran out. It’s now part of the not-so-exclusive club of overhyped SPACs that flamed out, joining the likes of WeWork and Vacasa.

Let’s be honest: the collapse of Sonder wasn’t shocking. The red flags were everywhere: mounting losses, desperate pivots, and a licensing deal with Marriott that smelled more like desperation than a long-term play. What was surprising? Just how poorly Marriott handled the whole thing, from due diligence on the deal to guest experience on dissolution.

After cutting ties with Sonder just days before it filed for bankruptcy, Marriott left guests scrambling, many mid-stay, with little more than a vague “we're here to help” email. Some were told to leave immediately, with no rebooking support, no credit, and no clear answers. A few guests didn’t even realize they’d booked with a Sonder property, because they booked through Marriott. So much for brand promise.

For a company that prides itself on consistency and guest trust, this was an unforced error. Licensing 140 properties (7,700 romes) with a partner that couldn't integrate properly, couldn’t sustain operations, and clearly didn’t have a solid runway? That’s not just a Sonder problem; that’s a lapse in Marriott’s strategic judgment.

And the signs weren’t subtle. Weeks before the collapse, Sonder disclosed in SEC filings that it was at risk of delisting, lacked enough liquidity to operate for the next 12 months, and had ongoing legal issues, including an investor lawsuit over accounting errors.

Meanwhile, Marriott had just launched “Sonder by Marriott Bonvoy,” a co-branded soft-brand collection built around this shaky foundation. That 20-year agreement lasted about 14 months.

Someone's got some ‘splaining to do?

Read More

TripAdvisor Lost the Plot — and Now 20% of Its Staff

Vintage photo of our Editor-in-Chief working through some Tripadvisor pricing frustration.

TripAdvisor just announced sweeping layoffs of about 20 percent of its staff across its core brand and Viator in a major restructuring that aims to refocus on experiences and AI-driven trip planning.

TripAdvisor had a golden opportunity to become the go-to source for travel advice. Instead, it overmonetized the platform, cluttered the user experience, and watched its trust erode. Sponsored placements crowded out authenticity. The very thing that made it valuable, credible user reviews, got buried under paid content and ads. Google soon surpassed them as the go-to site for reviews, and generative AI, such as ChatGPT, will likely take the lead as the new trip advisor (pun intended).

Now the company says it will narrow its focus, manage its core legacy business for profitability, and chase growth in experiences and AI. (When you start calling your main business “legacy,” I’d say the writing’s already on the wall.)

Our read:  The ship may have sailed. Travel discovery and trust have already shifted elsewhere. Cutting staff and reorganizing operations may buy time, but probably not relevance. Even with modest earnings growth in Q3, the company’s latest pivot feels more like survival mode than a bold reinvention. The platform that once helped travelers navigate the world now seems lost.

Google Cracks Down on Misleading Hotel Prices (Finally!)

As of early November, Google is now enforcing a major update to its Meta Price Accuracy Policy to clean up the hotel metasearch space. The message is clear: if the rate isn’t bookable and clearly shown and available on the booking website, it doesn’t belong.

The new rules require that the rate displayed on Google must match the most prominent, visible, and bookable price on your landing or booking page,  no hidden fees, buried rates, or fine-print surprises. All mandatory taxes and fees must be included in the total price upfront. If not, your ads and free booking links may be penalized, pushed down, or removed entirely.

Google is also banning indirect listings from ineligible or suspended partners and tightening the leash on meta-on-meta redirects, which should reduce rogue OTA activity and create a fairer playing field.

But let’s be clear: it won’t solve rate parity violations or stop gray-market OTAs from undercutting with discounted wholesale inventory. For this, hotels need to take action at the source, which as most revenue managers know, is no easy task. The process to stop bad actors remains the same: tightening distribution contracts, cutting off bad actors, and using rate integrity tools to monitor and enforce compliance.

If you’ve been playing it straight, this is a win. If you’ve been using “rates starting from” that are not actually bookable or do not include fees, it’s time to clean up your feeds.

Bottom Line: If the rate you show isn’t bookable, you won’t be showing up at all.

Industry Events

• PATA Hawai‘i & TTRA Hawai‘i 2025 Industry Holiday Breakfast - December 5, 2025 (Honolulu)

*If you have industry events to share, please email me at dan@hawaiihotelhui.com.

Spotlight on Hawai‘i Hospitality Opportunities

• Area Director of Sales - Hilton Hawaiian Village Waikiki Beach Resort (Oahu)

• Travel Industry Sales Manager - Four Seasons (Oahu)

• Marketing Manager - Highgate (Oahu)

• Sales Manager - Royal Lahaina Resort (Maui)

• Area Marketing Manager - Outrigger Hospitality Group (Big Island)

*If you happen to have any job openings, let me know. I will be glad to include them in the newsletter; send the job link to dan@hawaiihotelhui.com.

Mahalo for all the feedback! Funny, sharp, concerned, and occasionally unprintable. As always, we don’t necessarily agree with everything here, but here at HHH, we always welcome opinions that can strike a deeper conversation. Keep it coming!

Let’s dive in.

Weed Watch: Poll Results Are In
Last issue, we asked whether Hawaiʻi should legalize recreational cannabis. You voted:

• ✅ Support: 69.5%

• ❌ Do Not Support: 30.5%

Nearly 70% of the Hui favor legalization, no word on how many of them voted with one hand in a bag of Maui onion chips.

Quick Comments

• “Quality news & insights, Professor Dan Wacksman!”

• “Start watching the debt at a lot of the Oʻahu and Maui hotels.” (it was in email but felt like a whisper)

• “Hard to hide 2025 full-year results when Q3 has been reported. Obviously, 2026 is being presented as the turnaround, or stock prices would decline. It would be interesting to compare predictions for 2025 in October / November of 2024 and then compare with actual results.🤔”

Industry Memory Lane

• “Nice job with this newsletter. Interesting fact: I was with Host Hotels when Chris Nassetta (now CEO of Hilton) bid on the Four Seasons Maui, and Michael Dell outbid him. He was so upset over it that he ended up making a ridiculous offer to buy the Fairmont next door. They still own it today.”

  • HHH Note: We love a little behind-the-scenes hospitality lore. Also, a reminder: CEOs, they’re just like us. Except with bigger checkbooks and longer grudges.

KS Land Sale – The Reader Response Begins

We mentioned the Royal Hawaiian deal in this issue and previewed it on LinkedIn. Unsurprisingly, a few readers had thoughts.

• “The real question is, where are they going to reinvest the proceeds? Here in Hawaiʻi, or elsewhere? Lots of capable folks at Kamehameha Schools, and lots of needs to be met in the communities they serve. It's a shame that they have to expend resources defending their mission. #Imua”

• “The question is obvious, and I'm sure it's on all of our minds. We have a powerful mission here, but when we're selling land to foreign investors, how does that serve the community here on the islands? More jobs, fewer jobs, fewer opportunities under a different regime? Our island will no longer be ours if we continue to sell our precious commodity piece by piece. The question is why.”

I suspect these won’t be the last thoughts we get on this story.

Got feedback? Fire it off to dan@hawaiihotelhui.com.

About Us

Hawaiʻi Hotel Hui was started by hotel industry veteran Dan Wacksman, the CEO of Sassato, a Hawaiʻi-based consultancy that combines deep local expertise with a global perspective to help hotels and travel businesses overcome challenges and thrive. With a team of seasoned industry professionals who call Hawaiʻi home, Sassato offers an intimate understanding of the market, culture, and key players, paired with decades of experience in technology, marketing, revenue management, operations, finance, and overall strategy.

While Hawaiʻi is our backyard, our global footprint enables us to bring best practices from around the world. At Sassato, we don’t just consult, we deliver results with a no-nonsense approach to getting sh*t done.

Recent engagements include brand transitions, system selection and implementation (e.g., website, booking engine, PMS, CRS, CMS, CDP, F&B, and other acronyms), feasibility studies, competitive analysis, strategic planning, training, meeting facilitation, and audits in marketing, distribution, and technology. If you need help, we’ll either assist you directly or connect you with the right experts. Our ultimate goal is to be a trusted partner and resource for Hawai‘i hotels.

Aloha {{first name |}}!

Welcome to this month’s Hawaiʻi Hotel Hui Insider.

First, a big mahalo to this issue’s sponsor, Tambourine - the hotel marketing technology pros behind some of the industry’s best websites. From full-service marketing to their new hotel and air booking engine, they’re helping hotels rethink digital strategy from top to bottom. If your online game needs a tune-up, give them a look.

In this issue: Hawaiʻi debates recreational cannabis as Japan side-eyes our policy shifts, Mandarin Oriental Honolulu continues its disappearing act, and a shovel-ready hotel site hits the market in ʻEwa. Plus, a look at hotel earnings (spoiler: flat is the new up), and browser wars that might matter more than you think.

And a heads-up: next issue, we’re officially launching the Hawaiʻi Hotel Hui website. More jobs. More news. More no-fluff insights, all in one place. Stay tuned.

Know someone in the industry who should be reading this? Forward it their way. The Hui is growing because of you.

Not on the list yet? You can join the hui below, no spam, no cost, just real talk.

Thanks for sticking with us. The Hui’s just getting started!

Let’s dive in.

Mahalo,

Dan Wacksman
Hawaiʻi Hotel Hui Insider Editor-in-Chief 😄

Pakalōlō Panic: Will Japan Ghost Us Over Ganja?

The Retail Merchants of Hawaiʻi are fired up about recreational cannabis, and not in the celebratory sense. Their big fear? That legal weed could scare off Japanese tourists who still equate cannabis with hard drugs. Tour wholesalers, airlines, and even the Honolulu Prosecutor's Office are echoing concerns.

California legalized it, and its Japanese arrivals didn’t vanish. Neither did Colorado’s.

Let’s be real, Hawaiʻi already allows medical cannabis, and anyone walking through Waikīkī knows enforcement is inconsistent. What if, instead of hiding from it, we treat cannabis like alcohol or cigarettes: legal, taxed, and regulated?

Are we safeguarding culture or just high on our own supply?

Forget Armond, We’ve Got Konrad

Konrad Gstrein has been named regional VP and general manager of the Four Seasons Resort Maui at Wailea, returning to the same property where he began his Four Seasons career back in 2001.

The resort is owned by MSD Capital, Michael Dell’s firm. Sound familiar? It should. MSD also owns Four Seasons Hualālai (the hotel and the land), which we covered in the last issue.

Unlike the GM famously portrayed in The White Lotus, filmed at this very resort, we expect Konrad’s storyline will have less drama and more RevPAR.

Welcome back, Konrad, and best of luck in your new role!

For those who have not seen White Lotus Season 1, you really need to check it out.

The New Amenity Parents Actually Want
-Featured Partner-

Let’s face it, room upgrades are great, but time to relax? That’s priceless. Tutti Vacation Babysitters is redefining hotel childcare by connecting families with verified, background-checked local sitters who go beyond watching the kids. They lend a hand with the real stuff: unpacking suitcases, running errands, giving parents (especially moms) a moment to breathe.

This fair-trade platform gives parents the freedom to choose their own verified, background-checked babysitter. Families enjoy transparent pricing, low booking fees, and fair pay for sitters, creating a better experience for everyone. With Tutti Vacation Babysitters, parents can relax knowing their children are cared for, their needs are supported, and their choice helps empower local communities.

World Class Golf Course, Waterpark, Is a Hotel Next?

A 5.5-acre resort-zoned parcel fronting the lagoon at Wai Kai at Hoakalei is officially on the market. Fully entitled, utilities in, roadways done, ready to go. Asking $25 million, with room for 225–250 keys.

It’s part of the long-in-the-works Hoakalei Resort in ʻEwa Beach, 726 acres with homes, a private Ernie Els golf course, and the recently opened Wai Kai water adventure complex.

Colliers is leading the listing, and they’ve already had a few groups fly out. The pitch? Fee simple, lagoon-front, shovel-ready, Oʻahu. Those don’t come up often.

Read More

*Note to my friends at Wai Kai, I know you are not a waterpark, but a “water adventure” just didn’t work with our clever the headline.😉

Whatever Happened to the Mandarin Oriental Honolulu?

We noticed that Mandarin Oriental Hotels was recently taken private by its majority owner, Jardine Matheson. Which got us thinking: what’s going on with the Mandarin Oriental Honolulu?

There was a flurry of press releases a few years ago, but the last update we could find was back in 2023. Since then, radio silence, and the last time I drove by the site, I didn’t see a whole lot of activity. 

If any of our well-informed readers have intel on the status of this project, we're all ears. Otherwise, we may need to go into Keith Morrison reporting mode: “It was a bold announcement…. Two parcels. Billions of dollars. Five years, they said. But now? Just a concrete slab and questions.”

Hotel Performance

Hotel performance data will be published in the first issue of each month.

Click here for the full DBEDT breakdown: Seats, stays, and then some.

Flat Is the New Up? Q3 hotel earnings are out, and 2025 just got downgraded, again.

Inbound is soft, group is sluggish, and government travel is MIA. Most chains are shifting focus to 2026 and leaning into AI as a lifeline. Here’s the skinny on Q3 earnings calls:

• Hilton: U.S. RevPAR down 2.3%; group business off 4%. AI and loyalty tweaks are the story, but 2025 guidance is now flat.

• IHG: Gov travel dropped 20% in the U.S., pulling Q3 RevPAR to -1.6%. Still clinging to 1.4% growth next year, but it’s mostly hope.

• Wyndham: RevPAR tanked 4.8% in Q3; 2025 outlook now down 2–3%. The AI assistant is live in 7% of hotels, and early results look promising.

• Accor: The lone optimist. Q3 RevPAR up 0.8% (3.2% YTD), holding 2025 forecast at +3–4%, thanks to strong luxury and Middle East growth.

Three Ways Hotels Are Leaving Money on the Table
-Featured Partner-

Revenue leakage doesn’t start when you discount; it starts long before a guest hits the booking button.

First: pricing inconsistency. Even small differences in nightly rates or fees across channels erode trust and shift bookings away from your most profitable path.
Second: content friction. If room types, amenities, or photos don’t align everywhere guests shop, confusion costs you conversions.
Third: unleveraged direct value. If your best offer isn’t the easiest to understand or book, you’ve already lost – they’ll default to whatever feels simplest.

These fixes don’t require major system changes - just clarity, consistency, and planning. These are the quiet alignment fixes that ensure more of the revenue you influence actually reaches the bottom line.

Wyndham Solves Loyalty by Charging for It

Wyndham just launched Wyndham Rewards Insider, a $95/year subscription that feels more like a Costco card for travel than a traditional loyalty tier. Members get hotel discounts, airfare and cruise deals, concierge access, Gold status, and a few extras tossed in.

They’re not alone in the loyalty-for-cash game. IHG has its $200 Ambassador program. And not to be outdone by the global brands, Hawai’i’s own Outrigger offers a $299 Platinum Membership, with upgrades, resort credits, and other perks across its Hawaiʻi and Asia-Pacific portfolio.

Recurring revenue models (aka subscriptions) have been Wall Street’s favorite business model for over a decade, and, as usual, hotels are late to the game but are finally giving it a shot.

What sets Wyndham apart is the scope. This isn’t just about hotel perks; it’s about bundling in non-Wyndham perks. Flights, cruises, events, even a concierge. And notably, Wyndham says it’s absorbing the discount costs, not pushing them to franchisees. I am guessing that is until someone in accounting remembers how franchise math works.

If loyalty is going to evolve, why not turn it into a product people are actually willing to buy?

What do you think?

K-Shaped Recovery Joins the HHH Dictionary
(Like bifurcation, but with better branding)

Another addition to the HHH Dictionary: K-shaped recovery, where companies serving affluent customers thrive, while those targeting low and middle-income consumers fall behind. And in Q4, the travel industry is living it.

Winners: Delta, United, and Southwest are forecasting record holiday quarters, driven by premium international travel and high-spend customers. Amex users are still swiping freely, and luxury travel bookings are up double digits.

Losers: Hilton, IHG, and Wyndham are all reporting soft U.S. demand and falling RevPAR. Wyndham cut its full-year guidance after a rough Q3. Gen Z and millennial travelers are pulling back, and brands like Spirit and Frontier are feeling the squeeze.

The takeaway? If your business depends on volume over margins, this isn’t your recovery. But if you’re selling to the top of the K, things are looking just fine. 

Hope you're taking notes, all these new buzzwords will be showing up on the HHH final exam 😉

The browser wars just got agentic

Browser Wars: The Sequel No One Asked For (But Might Be Worth Watching)

Back in the ’90s, Microsoft steamrolled Netscape and crowned Internet Explorer the king of the internet. That is, until Chrome showed up and took the crown.

Now, the browser wars are back. Only this time, the fight isn’t about speed or tabs. It’s about who can think for you.

We flagged Comet a while ago, it’s Perplexity’s AI-powered browser with a built-in assistant that reads your screen and helps with email, scheduling, and research.

Now OpenAI has entered the ring with Atlas, currently only available for Mac. And it doesn’t feel like a browser at all, it feels like ChatGPT became your browser. There’s no traditional search bar. No frantic tab hopping. Just ask “What’s the latest on HTA governance?” or “Compare hotels across Waikīkī,” and it does the legwork. Add Agent Mode, and the AI doesn’t just find answers; it can complete tasks for you (e.g. make bookings, fill out forms, etc.)

It’s not perfect yet. But it’s clear where things are heading. The browser isn’t just a place to search and manage bookmarks anymore; it’s becoming your assistant. And no one’s going to announce when this shift becomes the norm, so it’s probably worth experimenting now, while you’ve still got the luxury of curiosity over necessity.

Want to dive deeper?
📎 Meet OpenAI Atlas
 📎 Comet by Perplexity

Industry Events

AHICE Aloha: Big Voices, Real Talk
-Vendor Pop-Up-

Over 50 hotel leaders will hit the stage at AHICE Aloha this November: Outrigger, Marriott, Wyndham, Springboard, Colliers, HVS, and, most importantly, Hawaii Hotel Hui! The event will be held at Prince Waikiki on November 7th.

The agenda? Development, operations, investment, tech... and the real-world issues shaping Hawaiʻi hospitality.

• Worthshop9 - November 6th-7th, 2025, (Wailea, Maui)

• Aloha Hotel Industry Conference and Exhibition (AHICE Aloha) - November 7th, 2025 (Oahu) 

• Holomua 2025 Presents the Return of the Ko‘i Awards Gala – The Met Gala of Maui  - November 14, 2025 (Maui)

*If you have industry events to share, please email me at dan@hawaiihotelhui.com.

Spotlight on Hawai‘i Hospitality Opportunities

• Group Sales Manager – ʻAlohilani Resort Waikīkī Beach (Oʻahu)

• Sales Manager – Royal Lahaina Resort (Maui)

• Area Marketing Manager - Outrigger (Big Island)

• Director of Marketing – 'Auana – Resident Shows (Oahu)

• Regional Director Condo Operations - Outrigger (Maui) 

*If you happen to have any job openings, let me know. I will be glad to include them in the newsletter; send the job link to dan@hawaiihotelhui.com.

Mahalo for all the feedback, compliments, corrections, and cautionary tales alike. Whether you’re calling out our typos or calling out $160M roofing budgets, we appreciate that you’re reading. (And firing back.)

Here’s what’s landed in the inbox lately…

Correction Station:
An Akamai reader flagged an error in our last issue. We mistakenly said the Hampton Inn & Suites Kapolei was a new PM Hotel Group project. It’s not. That property's been open since 2016 and is managed by Aqua-Aston. The actual PM project is a different Hampton/Home2 Suites listed as “coming soon” on their site. Mahalo for keeping us honest.

Quick Comments

• “Thanks for the new vocab word ;)”

  • Shoutout to those of you who learned “enshittification” from us.

• “Is it just me, or does that price point seem obscene?”

  • This was about the $160M Convention Center repairs. Our reply: Not just you. That roof better come with solar panels, a heliport, and Beyoncé.

On the international travel slowdown:

• “Once international tourists discover other destinations, their loyalty to the USA or Hawaiʻi may be gone for good.”

• “There are so many factors contributing to soft international demand, and some seem more long-term than the current government shutdown.”

On Cultural Understanding:

These came in after we covered management turnover and hotel leadership dynamics. They speak for themselves:

• “Understanding the intricacies of local and Native Hawaiian values is still paramount to doing business in Hawai‘i. If we begin to think or practice otherwise, then who are we as a destination?”

• “Local understanding is crucial for a hotel operator. Not only to ensure properties hold Hawai‘i's spirit for the guests but also for those who are actively working within it.”

Want to weigh in on something we got wrong, or right? Disagree with our takes? Fire back at dan@hawaiihotelhui.com, and your comment might appear (anonymously) in the next issue.

About Us

Hawaiʻi Hotel Hui was started by hotel industry veteran Dan Wacksman, the CEO of Sassato, a Hawaiʻi-based consultancy that combines deep local expertise with a global perspective to help hotels and travel businesses overcome challenges and thrive. With a team of seasoned industry professionals who call Hawaiʻi home, Sassato offers an intimate understanding of the market, culture, and key players, paired with decades of experience in technology, marketing, revenue management, operations, finance, and overall strategy.

While Hawaiʻi is our backyard, our global footprint enables us to bring best practices from around the world. At Sassato, we don’t just consult, we deliver results with a no-nonsense approach to getting sh*t done.

Recent engagements include brand transitions, system selection and implementation (e.g., website, booking engine, PMS, CRS, CMS, CDP, F&B, and other acronyms), feasibility studies, competitive analysis, strategic planning, training, meeting facilitation, and audits in marketing, distribution, and technology. If you need help, we’ll either assist you directly or connect you with the right experts. Our ultimate goal is to be a trusted partner and resource for Hawai‘i hotels.

Aloha {{first name |}}!

Welcome to this month’s Hawaiʻi Hotel Hui Insider.

A big mahalo to our issue sponsor, Castle Resorts & Hotels. With decades in the game and properties across the islands, Castle continues to shape what hospitality looks like in Hawaiʻi, and we’re stoked to have them as part of the Hui!

In this issue, a historic Kauaʻi hotel hits the market for $26M, the Panda Express empire moves into extended stay, PM Hotel Group keeps expanding, and the OTAs aren’t being disrupted; they’re embedding themselves directly into your guests’ AI-driven planning journey.

We also have a few free tickets to give away for AHICE Aloha. Want in? Repost any HHH story on LinkedIn, tag us, and email a screenshot to dylan@hawaiihotelhui.com. First-come, first-served!

And a quick teaser: next month (if all goes well), we’re launching the Hawaiʻi Hotel Hui website. Think of it as your favorite inbox read, but with more job listings, vendor directories, event info, and deeper stories, all in one place (and still zero fluff). 😉

Know someone in the industry who should be reading this? Forward it their way, growing the Hui helps keep this thing going.

Not on the list yet? You can join the hui below, no spam, no cost, just real talk.

Thanks for sticking with us. The Hui’s just getting started!

Let’s dive in.

Mahalo,

Dan Wacksman
Hawaiʻi Hotel Hui Insider Editor-in-Chief 😄

Historic Kauaʻi Hotel Lists for $26M

Last issue, we talked about the sale of the Manago Hotel, the oldest hotel on the Big Island. Now we’ve learned that the Kauaʻi Inn, the island’s first hotel dating back to 1890, is on the market for $26 million. It’s listed by Sotheby’s, which isn’t your typical hotel brokerage route.

Located on 2.75 acres in Niumalu, the 48-room property pencils out to $437K per key and includes a manager’s house, a resort-style pool, and individual TMKs for each unit (meaning each one has its own deed and could theoretically be sold off condo-style, a rarity in hotels). With Urban-Open zoning and condo status, the playbook is wide open: keep it boutique, reposition it, or redevelop entirely.

If you are interested in the listing and have a cool 26 million lying around, Sotheby’s created a microsite for it; click here to see it.

From Orange Chicken to Extended Stay (sorry, I couldn’t help myself)

The former Pacific Business News building at 1833 Kalākaua (across the Ala Wai from the Convention Center) is being planned for conversion into a Residence Inn by Marriott.

The 10-story building was bought in 2017 for $14.3 million by Panda Express founders Andrew and Peggy Cherng, who are also tied to the planned $2 billion Atlantis resort at Ko Olina. Permits list the renovation value at $53.5 million, but work hasn’t started yet.

I was skeptical when an old Waikīkī office building was turned into the Hyatt Centric, but I’ll admit, they pulled it off. Except for the lack of lanais, it looks great. Just goes to show what a sharp designer can do with the right budget. When I look at this one, I still can’t quite see it... But who knows?

Read More

When AI Plans the Trip, Will It Pick You?
-Featured Partner-

Search isn’t what it used to be. Guests are skipping Google and asking AI what to book, and if your site isn’t structured right, you won’t even make the list.

Most hotel websites were made for human eyes, not machine brains. That’s a problem.

three&six builds brand, web, and content systems that speak both languages, so you’re visible, bookable, and one step ahead.

Built for humans. Structured for AI.

The Crowded Field of Hotel Management Companies

Maryland-based PM Hotel Group, which acquired Sightline Hospitality and its Hawaiʻi portfolio back in 2024, is adding firepower in the islands, naming Rodahl Leong-Lyons as Area Director of Sales & Marketing for Hawaiʻi. A kamaʻāina returning home, she’ll lead sales and revenue strategy across a growing portfolio that includes Queen Kapiʻolani Hotel, Holiday Inn Express Waikiki, and Hyatt Place Waikiki.

With two new Oʻahu projects in the pipeline—Hyatt House Ewa Beach and a Hampton/Home2 Suites listed as “coming soon” on PM’s website—PM is clearly expanding in the market and adding to the ever-growing list of management companies now vying for contracts.

Shutdowns, Sick Days, and a Billion Bucks a Week

According to the U.S. Travel Association, the federal shutdown is costing the U.S. travel economy $1 billion a week. TSA lines are long, and unpaid air traffic controllers are calling out sick.

Here in Hawaiʻi, it’s mostly business as usual, at least for now. HTA reports that state parks, beaches, and airports remain open, and even Pearl Harbor is operating with minimal disruption. Haleakalā and Hawaiʻi Volcanoes also remain open, though services are limited.  

Beyond the shutdown, inbound international travel is projected to drop 6.3% in 2025, according to U.S. Travel’s revised forecast. Canadians, one of our steadier markets, are continuing to cancel trips over political tensions. Air travel from Canada to the U.S. fell a whopping 27% in September! A Longwoods International survey showed 63% of Canadians are less likely to visit the U.S. due to policy and politics. Hawaiʻi is currently tracking 9.4% down for Canadians, and add that to the Japanese who have not returned since the pandemic. HTA, we have a problem!  

At The Lodging Conference in Phoenix earlier this month, economist Bernard Baumohl called this moment “one of the more bizarre” in U.S. economic history, citing inflation, uncertainty, and political chaos as a drag on long-haul leisure demand. 

AHICE Aloha: Big Voices, Real Talk, and Free Tickets (Maybe)
-Featured Partner-

Over 50 hotel leaders will hit the stage at AHICE Aloha this November: Outrigger, Marriott, Wyndham, Springboard, Colliers, HVS, and, most importantly, Hawaii Hotel Hui! The event will be held at Prince Waikiki on November 7th.

The agenda? Development, operations, investment, tech... and the real-world issues shaping Hawaiʻi hospitality.

Want in? We’ve got a few free tickets to give away. Repost any HHH story on LinkedIn, tag us, and email a screenshot to dylan@hawaiihotelhui.com. First-come, first-served!

Save Your Way (AKA Give your customer away)

Hotels.com has launched a new “Save Your Way” feature that lets OneKey loyalty members choose between getting an instant discount now or saving that amount as OneKeyCash to use later on Expedia, Vrbo, or Hotels.com.

If your hotel is part of this program, Hotels.com can offer 15–20% off and call it loyalty. If you offer the same deal directly, get ready to receive a parity violation notice. 

Let's be clear, Hotels fund the discount, but Expedia keeps the loyalty credit, the data, and the relationship. The OTA looks generous; hotels foot the bill.

Plenty of properties will opt in without realizing what they’re giving up. 

For years, I have been preaching, NEVER offer on an OTA what you don’t offer on your own direct channels. 

OTAs Just Took Over the Chat

Just when you thought it couldn’t get more crowded at the top of the funnel, Booking.com and Expedia have found a new way to wedge themselves into your guests’ search journey, inside ChatGPT.

Yep. ChatGPT now pulls live hotel rates, images, and availability directly from OTA inventories via official plug-ins. Ask something like “Show me hotels in Waikīkī next weekend,” and you’ll get real-time listings from Booking.com and Expedia, no browser needed. For now, the actual booking still happens on their platforms.

And it’s not just ChatGPT. Expedia also partnered with Perplexity AI and its new Comet browser, embedding trip planning and OneKey loyalty perks directly into the interface, including Silver status just for downloading. No logins, no switching tabs, just AI-driven discovery, loyalty integration, and frictionless booking in one place.

Results from a Recent ChatGPT Search.

So no, the OTAs aren’t getting disrupted. They’re getting promoted. Everyone assumed LLMs would break the old model. Instead, they’ve become the newest distribution layer, and the OTAs got there first.

Here’s the disintermediation dilemma. OTAs provide clean, structured data from centralized systems. Most hotels run on fragmented tech stacks (CRS, PMS, and IBE, etc), all speaking different dialects. ChatGPT can’t, and won’t, parse all that. But it can pull seamlessly from a few big players who’ve already built for machine readability.

If this feels like Google Hotel Ads déjà vu, you’re not wrong. The funnel is narrowing again, and the OTAs are racing to own the top of it, this time by getting embedded in the AI tools travelers are beginning to trust most.

Have you played with Comet yet? You no longer need an invitation and can download it here.

Industry Events

three&six are on-island
-Vendor Pop-Up-

three&six will be in Hawaiʻi Oct 26–31, visiting partners on Oʻahu, Maui, and Hawaiʻi Island. If you’re exploring new digital support, curious about 2026 trends, or want to see how your property shows up in AI search, let’s start with a quick pre-meeting. From there, we’re happy to stop by or host a pau hana with your team.

Win a Free Ticket to AHICE Aloha
-Vendor Pop-Up-

We’re giving away free tickets to AHICE Aloha (Nov 7, Prince Waikīkī).

Here’s how to claim one:

1. Repost any HHH story on LinkedIn

2. Mention Hawaiʻi Hotel Hui in your caption

3. Email a screenshot to dylan@hawaiihotelhui.com

First-come, first-served.

Join top hotel execs for a full day of real talk, trends, and industry insight.

• MPI Aloha Chapter Kauai Pau Hana - October 24th, 2025 (Lihue, Kauai)

• Worthshop9 - November 6th-7th, 2025, (Wailea, Maui)

• Aloha Hotel Industry Conference and Exhibition (AHICE Aloha) - November 7th, 2025 (Oahu) 

• Holomua 2025 Presents the Return of the Ko‘i Awards Gala – The Met Gala of Maui  - November 14, 2025 (Maui)

*If you have industry events to share, please email me at dan@hawaiihotelhui.com.

Spotlight on Hawai‘i Hospitality Opportunities

• Director of Marketing – 'Auana – Resident Shows (Oahu)

• Guest Services Manager - Marriott (Oahu)

• Regional Director Condo Operations - Outrigger (Maui) 

• Director Sales and Marketing - Highgate (Kauai)

*If you happen to have any job openings, let me know. I will be glad to include them in the newsletter; send the job link to dan@hawaiihotelhui.com.

Let’s be honest: writing this newsletter sometimes feels like yelling into the void. So when your feedback hits the inbox, whether it’s a one-liner, a hot take, or a thoughtful response, it’s a solid reminder that the Hui is real, paying attention, and not afraid to speak up.

Here’s what came in after the last issue…

Quick Takes

• “Fascinating. This is my first time looking at this.”

• “It’s worth maybe half what they’re asking for it.” [regarding the ʻEwa Hotel story]

• “That’s hilarious; I recognize her, great smile!” [about the “Ubiquitous Stock Photo Star”]

• “:) I saw her on a grocery store wall in Arue, Tahiti.” [about the “Ubiquitous Stock Photo Star” 😂]

Stronger Sentiments

• “It’s heartbreaking to see more of Hawai‘i’s land sold off rather than kept in local hands. Losing pieces of its heritage feels like losing a part of its soul.” [in response to the Michael Dell story]

On the Alaska–Hawaiian Merger

We received a thoughtful and personal note from a long-time Hawaiian Airlines employee after our August 20th piece on the Alaska merger. It was too long to include in full, but we hope this excerpt captures the heart of it.

Before we get to that, a quick note from me:
Mergers and acquisitions are messy. I’ve been through a few on both sides, and it’s always more “fun” being the acquirer than the acquired. On paper, it’s all about “synergies” and “scale.” In real life, it usually means hard decisions, with the acquiring company holding most of the cards. Leadership and salaried roles tend to get consolidated, and those positions almost always tilt toward the buyer. That hits especially hard here in Hawaiʻi, when those jobs end up moving to the continent.

Here’s what they shared:

“Thank you for your August 20th article about the Alaska Airlines acquisition of Hawaiian Airlines... As a long-time employee, I appreciated seeing public acknowledgment of what many of us have experienced since the merger. While [Alaska’s] statements are accurate, the reduction in non-contract roles represents a significant and underreported loss to our community.

This loss includes much of Hawaiʻi’s professional workforce—the analysts, marketers, finance, HR, and IT teams who helped build the airline over decades... The remaining jobs in Hawaiʻi are largely frontline roles, which, while critical, typically do not require higher education. The result is a workforce structure that suggests locals are fit only for blue-collar positions, while leadership and professional opportunities move elsewhere.

As someone who grew up in Hawaiʻi and hoped to retire with Hawaiian Airlines, it’s heartbreaking to see so many local careers end and advancement pathways leave our islands.

From a consumer perspective, I have nothing against Alaska Airlines... I actually prefer them over certain competitors.”

Keep the thoughts coming; whether it’s praise, critique, or theories about stock photo models.

Email dan@hawaiihotelhui.com, and your comment might show up here (anonymously, of course).

About Us

Hawaiʻi Hotel Hui was started by hotel industry veteran Dan Wacksman, the CEO of Sassato, a Hawaiʻi-based consultancy that combines deep local expertise with a global perspective to help hotels and travel businesses overcome challenges and thrive. With a team of seasoned industry professionals who call Hawaiʻi home, Sassato offers an intimate understanding of the market, culture, and key players, paired with decades of experience in technology, marketing, revenue management, operations, finance, and overall strategy.

While Hawaiʻi is our backyard, our global footprint enables us to bring best practices from around the world. At Sassato, we don’t just consult, we deliver results with a no-nonsense approach to getting sh*t done.

Recent engagements include brand transitions, system selection and implementation (e.g., website, booking engine, PMS, CRS, CMS, CDP, F&B, and other acronyms), feasibility studies, competitive analysis, strategic planning, training, meeting facilitation, and audits in marketing, distribution, and technology. If you need help, we’ll either assist you directly or connect you with the right experts. Our ultimate goal is to be a trusted partner and resource for Hawai‘i hotels.

Aloha {{first name |}}!

Welcome to this month’s Hawaiʻi Hotel Hui Insider.

First up, congrats to our issue sponsor Castle Resorts & Hotels, who take over management of the Waikīkī Circle Hotel on November 1. It’s the property’s first new operator in 30 years. See what happens when you sponsor the newsletter? 😉

Quick housekeeping before we dive in: we’re switching our email domain. Future issues will now come from dan@hawaiihotelhui.com and hhhi@mail.beehiiv.com, so if you want to actually see the newsletter (not fish it out of spam), please whitelist both. Curious how? We’ve got a quick how-to here.

Now, onto the fun stuff...

In this issue: a billionaire buys the land under his own hotel, Outrigger and Springboard swap execs, we have a new word of the week (bifurcation), and the HTA Conference delivers data, discussions, and our favorite stock model.

Know someone in Hawaiʻi hospitality who should be reading this? Forward it their way, sharing is caring (and helps us grow the Hui).

Not on the list yet? You can join the hui below, no spam, no cost, just real talk.

Stay tuned, and as always, mahalo for being part of the Hui!

Let’s dive in.

Mahalo,

Dan Wacksman
Hawaiʻi Hotel Hui Insider Editor-in-Chief 😄

Billionaires Land Club

A fund tied to Michael Dell just dropped $400 million to buy the land under the Four Seasons Hualālai on the Big Island. He already owned the hotel, but the land was held by the Kamehameha Schools (KS) Trust.

We’ve been talking about leaseholds lately, and this one’s a standout. It’s pretty rare for KS to sell land, because while a sale gives you a one-time profit, holding on generates steady income in perpetuity. 

For Dell, the math is easy. He now owns the property outright, which makes any future sale much cleaner and surely a lot more lucrative.

Just as a reminder: Larry Ellison bought 98% of Lānaʻi, including two of the three hotels, for $300 million back in 2012. He later picked up Hotel Lānaʻi, so he now owns all the hotels on the island (along with the Island). That is just pocket change for Larry, who recently had a one-day stock gain of $100 billion.

So yeah, Dell paid more for the land under one resort than Ellison did for an entire island.

Put that on your Monopoly board.

Let’s say Eliisons’ and Dells’ are unlikely to be like the Robinson family of Niihau (see entertainment section).

If you are interested in a deeper analysis of the investment, my friends at Powell & Aucello explain it in detail here.

Castle Joins the Circle

This month’s issue sponsor, Castle Resorts & Hotels, is also making headlines.

Starting Nov. 1, Castle will take over management of the Waikīkī Circle Hotel. It's the property's first new operator in over 30 years. It becomes Castle’s 18th property. The hotel was previously managed by Aqua-Aston.

I really liked this quote from Castle CEO Matt Bailey:

“The Circle has always stood out for its shape, but not always its presence. Castle plans to change that, honoring its 1960s legacy and keeping it family-owned and locally run. A refreshing angle in a market where ‘heritage’ is often little more than brochure copy.”

Congrats to Castle, will be interesting to see what they do with it.

Trading Places

Outrigger just hired Jason Pirock as VP of Global Brand Marketing, effective September 1. If the name sounds familiar, it’s because he was previously the Head of Marketing & Brand at Springboard Hospitality, who manage 13 properties here in Hawaiʻi (and many elsewhere).

In talking with Jason, the big driver behind the move was the chance to help shape Outrigger into a truly iconic global brand, and it doesn’t hurt that he gets to move to paradise. Aloha and Welcome, Jason!

AI is changing search. Are guests finding you?
-Featured Partner-

Most hotel websites were built for people, not machines. But that’s changing; guests won’t “search,” they’ll ask AI.

And if your content isn’t structured and human-friendly, you’re invisible.

three&six builds brand, web, and content ecosystems designed for discovery, by guests and machines.

Built for humans. Structured for AI.

Outrigger Owner KSL Refis, But Still No Exit

KSL Capital Partners just closed a $480 million refinancing deal on two of its Hawaiʻi properties: Outrigger Reef Waikiki Beach Resort and Sheraton Kauaʻi Coconut Beach Resort. Both are owned by KSL, but only the Reef is part of the Outrigger portfolio.

KSL used most of the proceeds to pay off existing loans and pulled out nearly $148 million in equity, while maintaining full ownership. Private equity rarely wants to tie up its own capital longer than necessary. If they can refinance, pay off old loans, and pull out equity while keeping control, they’ll do it. Debt becomes a tool for liquidity, in other words, more cash to buy more stuff.

Most private equity holds last 5 to 7 years; KSL is already at year 8+ into it’s acquistion of Outigger. For now, they’re holding (re-financing) and still investing in upgrading the properties.

Read More.

Notes from The HTA Conference

From left to right: Jason Gamel, Hannah Smith, Raul Mamani, Dan Wacksman

I had the chance to attend the HTA Annual Conference on September 22nd and 23rd, and was honored to moderate a panel on “The Evolving Landscape of Lodging in Hawaiʻi.” It was a packed two days of updates, data, and discussions. A Few Quick Hits from the HTA Conference (and my panel):

• Hotel Growth? Blink and You’ll Miss It. 

  • Since 2006, Hawaiʻi has added… wait for it… just 60 new hotel rooms. We’re now at roughly 43,236 rooms statewide (for scale, Vegas has over 150,000 rooms).

• Vacation Rentals: The Real Growth Story

  • Since 2006 legal vacation rentals jumped 839%, from around 2,400 to 17,531. And that’s definitely understated, as only legal units are counted in the DBEDT numbers.

  Convention Center: More than Just a Leaky Roof

  • Repairs include $114 million to fix leaks and another $48.8 million for visible upgrades, restrooms, A/V systems, and fresh paint, among other improvements. More Details Here.

  • The current forecast? Reopening in 2028. While I was excited by the plan outlined by Convention Center GM Teri Orton, I am a bit skeptical of the timeline, as construction, in general, and government-led construction projects are not known for being on time. 

• Water, Water Everywhere, But Not a Drop to Irrigate

  • Ran into several Maui friends at the conference, and let’s just say, losing the Sentry golf tournament hit hard. The financial loss is one thing (~$50 million). The reputational damage? Even worse. Future tournaments are in doubt, and visitors are left wondering if Maui’s ready for tourists.

• The Ubiquitous Stock Photo Star Lives On 

  • Years ago, while deep in marketing, I kept seeing the same face in ads for hotels, airlines, banks, you name it. I dubbed her the “ubiquitous Asian lady” because she was the Asian model in nearly every ad I saw. Turns out, she’s Rebecca Givens, a hapa Canadian model and the world’s most-used stock photo star. This 2016 article tells the story. Once you see her, you’ll spot her everywhere. Sure enough, she popped up at last week’s HTA conference on at least three occasions.  Still smiling. Some things change (HTA Drama, AI, OTAs, enshittification)… but some stock photos are forever.

Hotel Performance

Hotel performance data will be published in the first issue of each month.

Click here for the full DBEDT breakdown: Seats, stays, and then some.

From Enshittification to Bifurcation

In the last issue, we talked about enshittification, a term Rafat Ali has used to describe what happens when businesses slowly degrade when they shift from serving users to extracting profits. At first, they serve the customer, then shareholders, and eventually, everyone’s experience suffers. Hotels aren’t immune; loyalty programs, resort fees, and shrinking service levels are all symptoms of the same slide.

At the HTA conference, STR tossed another word into the mix: bifurcation. That’s the industry’s way of describing a split market, high-income travelers still spending big, while everyone else is pulling back. Luxury is holding strong while budget and select-service are under pressure.

And it’s not just consultants saying it. Marriott’s CEO flagged the same bifurcation trend at a recent investor event.

So now we’ve got names for two forces shaping the hotel landscape: enshittification (the slow decline of value) and bifurcation (travelers splitting into haves and have-nots). Both of these phenomena are on display in this now-viral TikTok video taking to task a Waikiki resort. Can you name the resort? Do you agree with here take? Are you enshitfying your guests experience?

AHICE Aloha: Big Voices, Bigger Conversations
-Featured Partner-

Over 50 hotel leaders from Hawaiʻi and beyond will take the stage at this year’s AHICE Aloha, including execs from Outrigger, Marriott, Wyndham, Springboard, Colliers, HVS, and more.

Expect sharp takes on development, operations, investment, and tech—plus a front-row seat to the issues shaping our industry.

We’ll be there. Will you? See the events section below for an opportunity to get some free tickets!

Ace in the Hole: Prince Hotels Goes Lifestyle

Seibu Prince Hotels is buying Ace Hotels (and its in-house creative arm) for about $90 million. The Prince brand feels a bit dated, and adding Ace gives them the lifestyle edge they’ve been missing. It also helps diversify their portfolio, important if they’re serious about their 250 hotels by 2035 growth plan. The deal adds nine properties (eight open, one in development), taking Prince’s total to about 95 hotels worldwide.

Seibu Prince currently has two properties in Hawai‘i: Prince Waikiki and the Westin Hapuna Beach. Maybe an Ace will be next? 

Minority Report or Big Bang Theory?

OK, I’m a gadget nerd, and quite possibly just a nerd. So when a friend showed up wearing Meta’s Ray-Ban smart glasses, I did what any reasonable person with a credit card and weak self-control does: I bought a pair immediately.

I mostly use them to take pictures without pulling out my phone, listen to music, and ask the AI random questions. The real-time translation feature is slick too, though the language options are still pretty limited.

Of course, days later, Meta dropped the Hypernova: their new $800 smart glasses with actual displays and a neural wristband for gesture control. Basically, Ray-Bans with a heads-up display and jazz hands. Think Minority Report, but instead of Tom Cruise, think Sheldon from The Big Bang Theory.

I’m enjoying the Ray-Bans, though I’m slightly self-conscious about looking like a glasshole. And honestly, I think I’m giving off more Sheldon than tech visionary.

Industry Events

three &six Is On-Island
-Vendor Pop-Up-

three&six will be in Hawaiʻi Oct 26–31, visiting partners on Oʻahu, Maui, and Hawaiʻi Island. If you’re exploring new digital support, curious about 2026 trends, or want to see how your property shows up in AI search, let’s start with a quick pre-meeting. From there, we’re happy to stop by or host a pau hana with your team.

Win a Free Ticket to AHICE Aloha
-Vendor Pop-Up-

Want to attend the 2025 AHICE Aloha Conference on November 7th, 2025 at Prince Waikiki - for free?

We’ve got a limited stash of comp tickets, and here’s how to grab one:

1. Repost any HHH story on LinkedIn

2. Shout out Hawaiʻi Hotel Hui in your caption

3. Send a screenshot of your post to dylan@hawaiihotelhui.com

First-come, first-served, while supplies last.

You’ll join hotel leaders and execs from across Hawaiʻi and around the world for a full day of panels, keynotes, and big industry conversations.

• MPI Aloha Chapter Kauai Pau Hana - October 24th, 2025 (Lihue, Kauai)

• Workshop Series - November 6th-7th, 2025, (Wailea, Maui)

• Aloha Hotel Industry Conference and Exhibition (AHICE Aloha) - November 7th, 2025 (Oahu) 

• Holomua 2025 Presents the Return of the Ko‘i Awards Gala – The Met Gala of Maui  - November 14, 2025 (Maui)

*If you have industry events to share, please email me at dan@hawaiihotelhui.com.

Spotlight on Hawai‘i Hospitality Opportunities

• Director of Marketing – 'Auana – Resident Shows (Oahu)

• Multimedia Content Specialist- Castle (Oahu)

• Director of Services - Marriott (Maui)

• Guest Services Manager - Marriott (Oahu)

• Regional Director Condo Operations - Outrigger (Maui) 

• Director Sales and Marketing - Highgate (Kauai)

*If you happen to have any job openings, let me know. I will be glad to include them in the newsletter; send the job link to dan@hawaiihotelhui.com.

I recently watched Kuleana: Niʻihau, and it totally pulled me in.

As alluded to in our billionaire update, Niʻihau and Lānaʻi are the only two privately owned Hawaiian islands (still don’t really get that). This short doc gives a rare peek into daily life on Niʻihau. Watch it here.

Parts are in English, but a good chunk is in ʻōlelo Hawaiʻi, not staged, not translated, just everyday talk. Hearing it used so naturally was one of the coolest parts, along with seeing the island and everyday life. If someone has to own an island (which I think is very strange), I’d rather it be someone like the Robinson family than a tech billionaire who looks like an evil villain from a Marvel movie.

I’m always grateful when people take the time to write in, whether it’s praise, critique, or unsolicited policy reform. Below are a few standouts from this month’s inbox. As always, I don’t necessarily agree with these takes… but I’m glad we’re talking about them.

Praise from the Peanut Gallery

• “Even though I’m not in the hotel business, I read every word. Fascinating insider stuff.”

• “Always love getting the inside scoop, especially that TikTok OTA bit. Social media is changing how families plan Hawaiʻi trips.”

• “Luxury is here to stay. People who can afford great service will keep paying for it.”

• “Love seeing a woman CEO take the reins 🙌🏽.” [Re: Hawaiian Airlines]

• “Congrats to Castle Resorts on the sponsorship, well deserved.”

HTA: Hype Team or Hall Monitor?

• “HTA keeps trying to be two things at once, cheerleader and cop. You can’t say ‘Visit Hawaiʻi!’ and then scold people for how they visit.”

• “Split the job: HTA does marketing. Give stewardship to another agency, Planning or Consumer Affairs, maybe.”

• “It is possible for one org to market and manage tourism if you hire the right leader and keep politics out of it.”

Want to weigh in? Agree? Disagree? Hit reply or email dan@sassato.com, and you might end up here next time, anonymously, of course.

About Us

Hawaiʻi Hotel Hui was started by hotel industry veteran Dan Wacksman, the CEO of Sassato, a Hawaiʻi-based consultancy that combines deep local expertise with a global perspective to help hotels and travel businesses overcome challenges and thrive. With a team of seasoned industry professionals who call Hawaiʻi home, Sassato offers an intimate understanding of the market, culture, and key players, paired with decades of experience in technology, marketing, revenue management, operations, finance, and overall strategy.

While Hawaiʻi is our backyard, our global footprint enables us to bring best practices from around the world. At Sassato, we don’t just consult, we deliver results with a no-nonsense approach to getting sh*t done.

Recent engagements include brand transitions, system selection and implementation (e.g., website, booking engine, PMS, CRS, CMS, CDP, F&B and other acronyms), feasibility studies, competitive analysis, strategic planning, training, meeting facilitation, and audits in marketing, distribution, and technology. If you need help, we’ll either assist you directly or connect you with the right experts. Our ultimate goal is to be a trusted partner and resource for Hawai‘i hotels.

Aloha {{first name |}}!

Welcome to this month’s Hawaiʻi Hotel Hui Insider!

A special thanks to Castle Resorts and Hotels for being our very first Issue Sponsor. They’ve been part of Hawaiʻi’s hospitality story for decades, and it shows in how they operate and who they sponsor. 😁 

This month we’ve got HTA déjà vu, a GM handoff at Marriott Waikīkī, more vacation rental delays (Big Island joins the club), and the hotel deal that… kinda wasn’t.

Plus: luxury’s recession-proof streak, TikTok’s OTA pivot, and a strong reader take on why HTA’s mandate might be broken beyond repair.

If you’ve been finding these updates helpful (or at least entertaining), we’d love it if you shared them with a colleague or friend. The more folks we bring in, the stronger this hui becomes.

Not on the list yet? You can join the hui below, no spam, no cost, just real talk.

Stay tuned, and as always, mahalo for being part of the Hui!

Let’s dive in.

Mahalo,

Dan Wacksman
Hawaiʻi Hotel Hui Insider Editor-in-Chief 😄

The Hotel Sale That Wasn’t: Oasis or Mirage?

Pacific Business News recently reported that New York’s Eagle Point Hotel Partners acquired the 96-room Oasis Hotel Waikīkī for $23 million. But I had a “wait, what?” moment, something sounded off.

After poking around and confirming with Ben Rafter himself (who knows a thing or two about these things), here’s what actually went down. Eagle Point partnered with Rafter to purchase the land under the Oasis, which had been held by the Japanese owner Hawaiʻi Sekitei Corp. The building itself is currently (already) owned by Rafter and Eagle Point.

So no, this wasn’t a full hotel acquisition, even though that’s how it reads. It was a land acquisition. 

As you might recall from a past issue, Ben recently merged his company, Springboard Hospitality, with Hotel Equities and took on the larger role as CEO for Atlanta-based Hotel Equities. And while Ben may be managing from Atlanta, you can see his heart (and wallet) are still here in Hawaiʻi.

Remember, as we’ve said before: hotels are complicated, and in Hawaiʻi, even more so. One Hotel can have a different landowner, building owner, manager, and brand. No wonder people get confused... even PBN. 😃

Ewa Hotel Waikīkī Hits the Market

Compare the Oasis land sale to the 92-room Ewa Hotel Waikīkī, which is up for sale at $21 million, and is unencumbered (as we mentioned last week, this means management and brand are at the discretion of the new owner). That is $228K per key for a leasehold property that runs through 2045. In our humble opinion, it seems like a steep price for a leasehold that will likely require a significant renovation.

Joe We Hardly Knew You!

A surprise announcement came last week (at least it surprised us). Hawaiian Airlines CEO Joe Sprague is out (retired, so they say), and Diana Birkett Rakow is stepping in, promoted from her role as Senior Vice President of Public Affairs and Sustainability at Alaska Airlines. Not the usual promotion path for a CEO, but with all the public relations challenges surrounding the acquisition, that skill set could only help. Aloha, Joe. Aloha, Diana.

Read More Here

They Said ‘No’ for Years, Then Quietly 4x’d Poolside Revenue
-Featured Partner-

For years, this luxury retreat on Oʻahu’s North Shore didn’t just avoid day guests, it avoided the idea of them.

With multiple pools, including an adults-only infinity pool and a family-friendly option, leadership questioned whether it was worth the risk to the guest experience. But in May 2025, curiosity (and FOMO) took over. Inspired by other Hawaiʻi resorts, they quietly rolled out limited pool passes through ResortPass and sold 30 in month one.

By June, they added one adults-only cabana and one family cabana per day. Both sold out, and revenue jumped 4x. Though inventory remains tight, ResortPass sales continue to grow, up 53% month-over-month.

It’s not headline-grabbing revenue, but it proves a point: even the most exclusive resorts can unlock new income without overcrowding the infinity pool.

Déjà Vu at HTA

HTA has named David Uchiyama as its new Chief Administrative Officer. He previously led HTA’s global branding from 2007 to 2015. Since then, he’s held senior roles at Island Air, Roberts Hawaiʻi, and HART.

He’s experienced, well-connected, and understands Hawaiʻi’s visitor industry as well as anyone. That said, some of his past roles, including during Island Air’s collapse and HART’s ongoing challenges, come with baggage.

Still, this appointment isn’t really about him. It’s about the agency. HTA is under increased scrutiny, has lost key staff, and is operating in a tough environment. Bringing in a steady hand like Uchiyama may help restore order, but it also feels more like a move to stabilize than to transform. We wish David the best of luck in the new role, and hope his experience helps guide the agency through this critical period.

Reminder: David will be taking on a role within HTA’s operating side, not the advisory board that has gotten all the press. As chief administrative officer, he’ll oversee the agency’s day-to-day functions.

Read More Here

Marriott Waikiki Swaps Out the Corner Office

We announced back in June that Jerry Gibson was leaving his post as GM of the Waikīkī Beach Marriott Resort & Spa to launch his own hospitality venture.

Jerry will continue with the property as an owner’s rep, but the hotel has now named Mark Weatherill (who surprisingly does not have a LinkedIn) as its new GM. A Marriott veteran with decades of leadership experience, Weatherill most recently was Complex General Manager at The Westin Galleria Houston and The Westin Oaks. Howdy and Aloha to Mark!

Big Island Pulls Up a Chair to the Delay Table

Last issue, we flagged how Oʻahu and Maui’s short-term rental reforms are stuck in neutral. Now Hawaiʻi Island is drifting the same way. Ordinance 25-50, the county’s new law for hosted short-term vacation rentals, was set to take effect December 20th, 2025, but is now expected to be pushed back to March 2026. 

The law requires owners to register their rentals, pay fees ($250 hosted, $500 unhosted), renew annually, and comply with health and safety regulations, with fines of up to $10,000 for violations. Platforms like Airbnb and Vrbo must also register and report monthly data. The delay is meant to give operators more time to comply, but it leaves yet another county in limbo on STR enforcement.

Recession-Proof, or Just Enshittified?

If your industry feed looks anything like mine, you've seen the flood of takes about the “recession-proof” luxury market. Powell and Aucello just reported that Hawaiʻi luxury RevPAR is up 9% year-to-date, even as upscale and upper-midscale properties are each down 14%. Nationally, STR shows the same pattern: luxury is holding, while the middle softens.

Then there’s Rafat Ali’s recent “Enshittification of American Travel” post on LinkedIn (worth a read), where he argues the industry has shifted from democratization to pure extraction.

Put that all together, and the questions get sharper: How long can the luxury tier stay insulated while the middle gets squeezed? Are middle-income travelers trading up, and taking fewer trips or going into debt to do it? Or is the wealth gap simply showing up in hotel performance?

Whether it holds or cracks, luxury’s outperformance is starting to feel like a signal.

BTW- My word for 2025 is now “enshitification.”

If AI Can’t Read You, Guests Can’t Find You
-Featured Partner-

Most hotel websites were built for human eyes, not machine brains. But that’s changing. Soon enough, your next guest won’t “search” - they’ll ask AI.

And AI doesn’t care if your site is pretty; if your content isn’t structured, strategic, and human-friendly, you’re invisible.

That’s where three&six comes in. They build brand, web, and content ecosystems designed for discovery - for guests and machines. It’s the happy medium between tried-and-true and what’s next.

Built for humans. Structured for AI.

Jump into the conversation with three&six - they’re having a lot of fun with this new era of digital marketing.

Brand USA’s Shrinking Stage

Brand USA just axed 15% of its staff after Congress gutted its federal funding this summer, cutting it from $100M to $20M. Inbound U.S. tourism is still hovering around 80% of pre-pandemic levels and slipping month-to-month. If D.C. can’t get its act together, no amount of glossy branding will fix the bigger problem: politics scaring off visitors.

Tick Tock… There Go Your Direct Bookings

TikTok is moving from dance trends to room sales. The platform has launched TikTok Go, an affiliate program where creators tag hotels in their posts and earn commissions on bookings. Combined with the new Booking.com integration, users can now watch a video, check rates, and book without ever leaving TikTok.

The mechanics are simple. Creators pick a hotel from TikTok Go, see the commission rate, and post content with auto-tagged booking info. Followers tap, book, and get confirmation in their TikTok inbox. Creators earn, TikTok gets stickier, and Booking.com captures the reservation.

Each booking that flows through TikTok and Booking.com means less direct control and more OTA reliance. Booking.com is covering the commissions for now, but does anyone want to take odds on how long before this becomes a “pay more, get featured” product?

The question is not whether TikTok can move rooms. The real question is whether hotels will let the middleman continue to own the funnel.

See a TikTok about it here

Industry Events

Vendor Pop-Up: three &six Is On-Island

Looking for a new digital agency, curious about 2026 trends, or want to see how our clients show up in AI search? three&six will be in Hawaiʻi next month (Oct 26th, 2025 - Oct 31st, 2025), visiting partners on Oʻahu, Maui, and Hawaiʻi Island.

We’d love to stop by your property or host a pau hana with your team. Reach out if you’d like to connect and set something up.

• Hawaii Women in Lodging and Tourism - Unleash Your Creative Power with Judi Holler - September 17, 2025 (Oahu)

  • *Note: Guys, you’re invited too. HIWIL events are open to all genders; don’t let the name fool you.

• HTA Hawaii Tourism Conference - September 22-23, 2025 (Oahu)

• HSMAI Hawaii/Aloha MPI Pineapple Pau Hana - Oct 16 @ 4:30 pm (Maui)

• Aloha Hotel Industry Conference and Exhibition (AHICE Aloha) - November 7th, 2025 (Oahu)

*If you have industry events to share, please email me at dan@hawaiihotelhui.com.

Spotlight on Hawai‘i Hospitality Opportunities

• Rooms Manager - Highgate (Oahu)

• Guest Services Manager - Marriott (Oahu)

• Regional Director Condo Operations - Outrigger (Maui) 

• Director of Front Office - Crescent (Oahu)

• Director Sales and Marketing - Highgate (Kauai)

*If you happen to have any job openings, let me know. I will be glad to include them in the newsletter; send the job link to dan@hawaiihotelhui.com.

Asia Travel Tech: A Blast from My Past

Before I planted roots in Hawaiʻi, I spent years bouncing around Asia during one of the most explosive periods in travel tech. I launched an OTA startup in Beijing, then led the Asia region for a major wholesaler based in Hong Kong. It was a wild time: scrappy, chaotic, and moving fast.

That’s why this new documentary from Siew Hoon Yeoh hit home. She’s long been one of the sharpest voices in the industry, and she does a great job capturing the energy of the era. It’s a thoughtful, well-produced look at how the Asian travel industry grew from stitched-together systems and faxes into the dynamic digital giant it is today.

Now, fair warning: this one’s a bit nerdy and definitely geared toward the travel industry crowd. But if you’ve ever sat through a GDS demo, dealt with room mapping drama, or remember when taking payment online was considered cutting-edge, you’ll probably enjoy it as much as I did.

It’s a fascinating watch, especially if you care about how fast travel is evolving and how much is still up for grabs.

I always say feedback is welcome, unless it’s about my typos.

Kidding… Mostly. 😉

This month, a reader emailed me to say, “Great issue! And excited for twice monthly! Keep up the great work.” Mahalo!

One lucky reader was bold enough to send me an email asking me if I had any more invites to the perplexity’s browser Comet, and it so happened that I did!  Which shows you my grandmother was right, it never hurts to ask! 

You might recall in the last issue, we asked in a Poll if you agreed with State Senator Wakai's LinkedIn post, where he said, “HTA is expected to grow the tourism sector and, at the same time, keep inconsiderate tourists out. I believe HTA should focus on marketing and have stewardship under another agency (Dept Consumer Affairs, or Office of Planning).”  

The results: 73% of you agreed with the sentiment, while 27% disagreed. 

One reader had a very strong opinion, and I am paraphrasing it a bit due to space limitations: 

“Wakai is right… Destination management isn’t their core competency, and they haven’t proven they can do it. DLNR may be a mess, but it’s their lane. HTA should be supporting, not substituting.

Also, let’s be real, the dedicated funding isn’t coming back. We’ve got an underfunded, unstable org with no mandate. Who’s going to take that CEO job at less than a good hotel GM’s salary? You want someone who can drive serious ROI for the state? Then pay them like they can. Just ask June Jones.”

Editor’s Note: June Jones made $800K coaching UH football. The current coach makes $700K, for a mediocre team (please, no hate mail) that loses money. Meanwhile, the HTA CEO leads a small agency tasked with influencing an industry responsible for ~$20 billion in annual spending and the associated jobs and taxes that come with that.

Got thoughts of your own? Sharp opinions? Personal vendettas? Just want to argue with a fellow reader anonymously? Send your take to dan@hawaiihotelhui.com, and maybe you’ll make it into next month’s inbox therapy session.

About Us

Hawaiʻi Hotel Hui was started by hotel industry veteran Dan Wacksman, the CEO of Sassato, a Hawaiʻi-based consultancy that combines deep local expertise with a global perspective to help hotels and travel businesses overcome challenges and thrive. With a team of seasoned industry professionals who call Hawaiʻi home, Sassato offers an intimate understanding of the market, culture, and key players, paired with decades of experience in technology, marketing, revenue management, operations, finance, and overall strategy.

While Hawaiʻi is our backyard, our global footprint enables us to bring best practices from around the world. At Sassato, we don’t just consult, we deliver results with a no-nonsense approach to getting sh*t done.

Recent engagements include brand transitions, system selection and implementation (e.g., website, booking engine, PMS, CRS, CMS, CDP, F&B), feasibility studies, competitive analysis, strategic planning, training, meeting facilitation, and audits in marketing, distribution, and technology. If you need help, we’ll either assist you directly or connect you with the right experts. Our ultimate goal is to be a trusted partner and resource for Hawai‘i hotels.

Aloha {{first name |}}!

Welcome to the latest from the Hawaiʻi Hotel Hui Insider! This month, we’re kicking off our new twice-a-month format. Look for fresh issues on the first and third Tuesday of each month.

This issue, we’ve got stalled vacation rental crackdowns, a century-old Waikīkī land lease that just sold for $215 million (yes, just the land), a “direct booking” startup with a middleman, and a new Green Fee council now figuring out how to spend $100 million a year.

But first, let’s talk SPAM, and not the canned kind your Aunty puts in fried rice. But the email kine.

Did you know the term SPAM used for junk mail is an actual acronym? It comes from a law called the Controlling the Assault of Non-Solicited Pornography and Marketing Act of 2003 (CAN-SPAM Act), and the acronym SPAM was a nod to this Monty Python skit. 

Why do I mention this amusing and somewhat random tidbit? Well, I received a few notes from people that they have to dig this newsletter out of their spam folder. If you're finding this in your spam folder, here is a link to directions to ensure that you get your HHHI fix, especially now that we are going twice a month! 

Now we can get back to the only kind of Spam we actually like. Unless you’re like me, team Portuguese sausage (no hate mail please).

As always, if you’ve been enjoying these issues, we’d be grateful if you passed them along to a colleague or friend. More voices make for a stronger hui!

And for those who haven’t subscribed yet, we welcome you to subscribe to the Hui below!

Stay tuned, and as always, mahalo for being part of the Hui!

Let’s dive in.

Mahalo,

Dan Wacksman
Hawaiʻi Hotel Hui Insider Editor-in-Chief 😄

The Ground Beneath Waikīkī Just Shifted (Literally)

After more than 100 years of holding the land beneath the Hyatt Regency Waikīkī, the Steiner family has sold their six parcels to Texas-based Montgomery Street Partners for $215 million. That’s right, this wasn’t the hotel, just the dirt under it, making this Waikīkī’s largest land sale in years.

Facade of the Hyatt Regency Waikīkī

For those unfamiliar: in Hawaiʻi, some of the most valuable land, especially in Waikīkī and urban Honolulu, is owned by large trusts like Kamehameha Schools, Queen Emma, Lili‘uokalani Trust, or by longtime family landholders like the Steiners. They lease out the land, and others build on it, and while the building often changes hands, the land under it usually doesn’t.

This setup isn’t just for hotels. Plenty of residential buildings and shopping centers sit on leased land, too. Owners control the structure, but not the land beneath it.

When the lease ends, if you can’t strike a new deal, you’re basically out of luck. Unless, of course, you can figure out how to move a building. 

Who Are the Steiners? (I had no idea, so I found out)

The Steiner family’s Hawaiʻi roots begin with James Steiner, who arrived from Bohemia (current day Czech Republic) in 1882 and rose from waiter to landowner. By the early 1900s, he had picked up prime parcels in downtown Honolulu and Waikīkī, including the land beneath what would become the Biltmore Hotel, which was demolished in 1974, then redeveloped into the Hyatt Regency Waikīkī. According to PBN, they also own the land below the AC Hotel in downtown Honolulu. 

As discussed in previous issues, hotels can sometimes be a tangle of owners and operators: one group can own the building, another manages the property, and another owns the flag. And sometimes the land itself belongs to yet another party, adding one more layer to the puzzle. I am exhausted just writing that!

Read More

Maui Delays, Honolulu Stalls - It’s a Staycation for Vacation Rental Regulation

As discussed previously, Bill 9, which would phase out thousands of short-term vacation rentals in Maui’s apartment-zoned areas, has cleared committee but still needs a full council vote.

The current proposal gives West Maui until the end of 2028 and the rest of the island until 2030. Hotel and resort-zoned properties are untouched for now, but expect lawsuits, amendments, and plenty more debate before anything is final.

Honolulu 90-Day STR Rule: Hurry Up and Wait

Honolulu’s much-discussed 90-day minimum rental rule, set to start next month, is still on hold. A federal court ruled in early 2024 that the city can’t enforce it until it creates a clear system for managing rentals that were legally operating before the new rule (“non-conforming uses”). That system isn’t ready yet, and as of now, I haven’t seen any timeline for when it will be. In the meantime, the city is still enforcing the old 30-day minimum rental period for most properties.

That lack of clarity and enforcement hasn’t gone unnoticed. This quote from Rob Robinson, President of Springboard Hospitality, during the HTA Oʻahu Virtual Community meeting (as reported by the Star-Advertiser), really shines a light on the issue:

[Efforts should be turned] toward vacation rental regulation and tax collection. We’ve passed a bunch of rules and we haven’t enforced them, and our governments — local and state — haven’t been able to really help in a meaningful way. We often get attacked in the hotel industry, but the reality is we were just as happy when we had 5 million visitors — the extra 5 million are not staying in our hotels; they are staying elsewhere.”

Green Fee Gets Its Brain Trust

As mentioned in past issues of HHHI, the Green Fee passed earlier this year, adding a 0.75% hike to the Transient Accommodations Tax (TAT) starting January 1st, 2026. Now, Governor Green has named a 10-member Green Fee Advisory Council to help decide how the projected $100 million per year will be spent. It’s classic government: create a massive fund to solve a problem, then forget to define the actual solution. What could go wrong?

Chaired by Climate Hawaiʻi’s Jeff Mikulina, the council includes voices from policy, science, community, and tourism. Since hotel guests will be footing most of the bill, it’s good to see at least one hotelier on the council: Outrigger CEO Jeff Wagoner, a seasoned hotel executive with a strong community lens.

It’ll be interesting to see how the money actually gets allocated. Hard not to be reminded that the TAT was originally earmarked specifically for tourism-related efforts… until it got sucked into the general fund. Will the Green Fee follow the same path?

Full Board and More Info Here

How One Wailea Resort Found $1M in Revenue - Without Adding a Single Room
-Sponsored-

A 5-star property on one of the most beautiful stretches of beach in Wailea had doubts about welcoming day guests. 

Before joining ResortPass in 2020, they had understandable concerns, among them: pool crowding and a potential hit to the guest experience. So they dipped a cautious toe in, offering just two cabanas with highly limited inventory.

Despite the hesitation, they pulled in $385,000 in sales that first year.

By 2023, they leaned in. The property offered up to 12 day passes per day (based on occupancy), doubled the cabana inventory, and began renting daybeds, welcoming up to 30 day guests daily. The result? Gross sales climbed to $892,000.

Now in 2025, this property is on track to hit its first million-dollar year. They recently added an Adult Spa Pass that drove $7,600 in sales in just 3 weeks. 

All while maintaining a serene, high-end guest experience. No drop in satisfaction. In fact, they ranked high in Condé Nast Traveler’s 2024 Readers’ Choice Awards.

This shows that luxury properties can attract day guests and generate substantial revenue, while still upholding a standard of excellence for their overnight guests.

So if you want to potentially drop a cool million to your bottom line without compromising the guest experience, and at no additional cost, it might be time to take a second look at your pool deck.

A Politician with A Rationale Idea?

I liked this quote on LinkedIn from Senator Wakai: “HTA is expected to grow the tourism sector and, at the same time, keep inconsiderate tourists out. I believe HTA should focus on marketing and have stewardship under another agency (Dept Consumer Affairs, or Office of Planning).” 

Curious to hear what the Hui thinks. 

When the Airlines Call You Back

Photo courtesy of Alaska Airlines

It still surprises me that so many people are reading HHHI, and I occasionally get contacted by readers and leadership at companies to clarify (and sometimes correct) information.

I love this for two reasons: one, it shows people are actually reading and paying attention; and two, I’ve always wanted this newsletter to be a conversation, not a monologue, and the Hui a community.

This week, I was glad to speak with Daniel Chun, Alaska/Hawaiian’s MD for Hawai‘i Public Affairs & Sales, about our recent piece on the Hawaiian–Alaska merger. He wanted to add some color to recent changes:

• While 787s shifted to Seattle (enabling one-stop Europe-Hawai‘i routes), all A330s remain Hawai‘i-based, with Pualani on the tail, the HA brand onboard, and major interior upgrades coming.

• The combined network opens up 100+ new North America destinations for travelers from Hawai‘i.

• Despite some non-union reductions, 600+ new frontline roles in Hawai‘i are being added; pilots, flight attendants, airport agents, and maintenance techs.

• New regional leadership team includes a CEO and many from Hawaiian Airlines, reinforcing commitment to a strong Hawai‘i HQ.

• An upgraded website and mobile app are launching this spring to enhance the HA guest experience.

• Alaska/Hawaiian is deeply invested in Hawai‘i and has, in fact, created an advisory board to help ensure this.

I appreciated the conversation and his candor. Their current intentions seem genuine, yet with any merger, the real test will come through actions over time. We’re hopeful, but also keeping a close eye.

Hotel Performance

Hotel performance data will be published in the first issue of each month.

Click here for the full DBEDT breakdown: Seats, stays, and then some.

DirectBooker: “Direct” Bookings… Via Someone Else

Apparently, the new way to break free from OTA dependence is to hire ex-Google and ex-Tripadvisor execs… to become your new middleman. DirectBooker, backed by former Tripadvisor CEO Steve Kaufer and ex-Google Travel head Richard Holden, wants to pump your hotel data straight into ChatGPT and Gemini so travelers can “book direct”, just not direct.

The pitch is that they’ll beat the OTAs at their own game by giving LLMs richer info and better prices. The reality? You’re still paying someone in the middle, only now it’s a startup with no product, no hotel partners, and a “pre-seed” war chest to burn. Sure, OTAs are expensive, but swapping one tollbooth for another isn’t exactly the revolution.

And while DirectBooker tries to wedge itself between hotels and guests, Airbnb is quietly muscling in from the other side. CEO Brian Chesky says the company is “going significantly more aggressively into hotels,” courting independents and filling gaps in high-demand markets. You might remember they acquired HotelTonight in 2019; now it looks like they actually plan to use it. Between AI intermediaries and Airbnb’s renewed hotel push, “direct” bookings may soon need their own air quotes.

Check out DirectBooker.com.

ADA Demand Letters: Pay Up or Lawyer Up

When I was head of digital for a hotel company, I got more than my share of ADA demand letters, basically legal shake-downs claiming our website wasn’t ADA compliant and asking for a quick payout to make it go away. Fortunately, we knew we were in compliance and had lawyers ready to push back.

Many hotels just cut a check to make nuisance cases go away, exactly what the attorneys in this cottage industry are banking on. But as Zarco Hotels proved, if you’re in the right and willing to fight, you can win… and even send the bill back to the sender.

Zarco didn’t just beat the claim; they were awarded over $142K in legal fees. The court called it what it was: a money grab.

The lesson? If your website’s in compliance, don’t panic. Document everything, get legal eyes on it, and think twice before writing that check. Not every demand letter deserves one.

Read More About the Case, Learn More About Website ADA Compliance

Is Google Chrome the next Netscape?

If you’re as old as me, you remember when Netscape ruled the web, until Microsoft buried it with Internet Explorer (which has since been rebranded as Edge), which was then slowly eaten alive by Chrome. It’s been a while since anyone seriously challenged the browser status quo… until now.

Between Comet (from the folks at Perplexity) and ChatGPT with browsing enabled, we’re not just talking about new browsers; we’re talking about replacements for the whole concept of browsing. These tools don’t just help you find links. They summarize, compare, cite, and even interact with websites for you. Ask ChatGPT to find the best hotel in Wailea next weekend, and it doesn’t send you to ten OTA tabs; it just tells you.

Comet pushes this further with its built-in assistant that reads articles, manages tabs, and automates tasks inside the browser itself. It's light, private, and yes, still buggy. But the direction is clear: the old browser is starting to feel like the PDF of the internet, technically useful, but a bit stale.

I’ve been playing with Comet (got an early invite), and it's impressive. The built-in assistant is genuinely useful, and the ability to summarize pages, manage tabs, and even take simple actions feels like a peek at what web browsing should be. It’s less about search and more about delegation, and that’s a big shift.

For hoteliers, marketers, and anyone who relies on search to drive bookings, this is not a passing trend. It is the future. AI is reshaping how people search and what they see. If your hotel isn’t built into the new conversation, it risks disappearing from view altogether.

If you are interested in trying Comet, you can check it out here: https://www.perplexity.ai/comet.

I’m grateful (and frankly shocked 😅) that people are actually reading, and especially thankful when you take the time to write in. 

This month’s feedback covered everything from ResortPass love to culinary redemption arcs. 

Here’s what’s come through the inbox lately: the praise, the pushback, and the occasional poetic rage. As always, all anonymous, all appreciated.

Praise

• “I look forward to your newsletter every month (and LinkedIn updates). Random note, but Eleven Madison Park just ended their vegan-only run and is back to an all-inclusive (meat-friendly) menu.”

  • Editor Note: Now  I need to start saving so I can go to EMP again!

• “Such great info, Dan – and love your personal touches to the stories.  Keep it up!”

• “Keep it up!  …  this information keeps me in the loop and in the know. I will continue to share the goodness by passing it on to help you grow.”

• “I love your newsletter! I’ve been sitting here reading the entire thing. I’m a big fan of ResortPass and have used it with my family on the Big Island. I’m going to forward this to all of the internal team, so I think you should be getting a few more subscribers.”

• “Thank you for another enjoyable and informative Hawaiʻi Hotel Hui Insider.   First time for me to hear the phrase vibe coding.”

Strong Opinions (Not Mine)

• “Awesome congratulations for my Braddah Lanai Tabura — no better selection to represent Hawaiʻi and Hawaiians … imua e nā pōkiʻi brah… 🎉💪👌”

• “Having been a customer with Hawaiian for 15 years and flying to Hawaiʻi at least twice a year gives me concerns. Flights from non-major hubs to Hawaiʻi and inter-island connections + cost have changed dramatically.”

• “It’ll go just like any other local company bought out by mainland corporations. No Aloha at all!!! I’m already seeing the trends and hearing the complaints!!”

On Hospitality

•  ‘It became clear that while we had built something meaningful, we had also unintentionally kept people out. This is the opposite of what we believe hospitality to be.’” Daniel Humm (Chef Eleven Madison Park).

  • Editor’s Note: For those who missed it, that quote came when Eleven Madison Park reversed their vegan-only menu. The message? If your version of hospitality isn’t welcoming everyone, it’s probably not hospitality. 

Industry Events

• Meetings Professional International (MPI) Aloha Chapter - The Wave Gala, Sep 6, 2025 (Oahu)

• Honolulu Tech Week 2025, September 8th- 14th, 2025 (Oahu)

• Hawaii Women in Lodging and Tourism - Unleash Your Creative Power with Judi Holler - September 17, 2025 (Oahu)

  • *Note: Guys, you’re invited too. HIWIL events are open to all genders; don’t let the name fool you.

• HTA Hawaii Tourism Conference - September 22-23, 2025 (Oahu)

• Aloha Hotel Industry Conference and Exhibition (AHICE Aloha) - November 7, 2025

*If you have industry events to share, please email me at Dan@sassato.com

Spotlight on Hawai‘i Hospitality Opportunities

• Vice President of Revenue Management - Springboard (Oahu)

• Vice President of Marketing  - Springboard (Oahu)

• Director of Catering and Events, Mauna Lani (Hawai’i Island)

• Guest Experience Manager - Highgate (Oahu)

• Assistant Front Office Manager - Highgate (Oahu)

*If you happen to have any job openings, let me know. I will be glad to include them in the newsletter; just send the job link to dan@sassato.com.

About Us

Hawaiʻi Hotel Hui was started by hotel industry veteran Dan Wacksman, the CEO of Sassato, a Hawaiʻi-based consultancy that combines deep local expertise with a global perspective to help hotels and travel businesses overcome challenges and thrive. With a team of seasoned industry professionals who call Hawaiʻi home, Sassato offers an intimate understanding of the market, culture, and key players, paired with decades of experience in technology, marketing, revenue management, operations, finance, and overall strategy.

While Hawaiʻi is our backyard, our global footprint enables us to bring best practices from around the world. At Sassato, we don’t just consult, we deliver results with a no-nonsense approach to getting sh*t done.

Recent engagements include brand/ownership/management transitions, system selection and implementation (e.g., website, booking engine, PMS, CRS, CMS, CDP, F&B), feasibility studies, competitive analysis, strategic planning, training, meeting facilitation, and audits in marketing, distribution, and technology. If you need help, we’ll either assist you directly or connect you with the right experts. Our ultimate goal is to be a trusted partner and resource for Hawai‘i hotels.