A Maui Hotel Mystery, Castle Grows, and Airbnb's Hotel Problem

June 15, 2026

Aloha !

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.

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.

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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.

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
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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.

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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.
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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.

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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

*If you have industry events to share, please email me at [email protected].

Spotlight on Hawai‘i Hospitality Opportunities

*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 [email protected].

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."

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 [email protected] or [email protected] 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.