Crown Jewel of Waikīkī Sold, Hawaiʻi Hotel Debt Mounts, and Google Cracks Down

November 18, 2025

Aloha !

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.

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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.

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?

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

*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 me know. I will be glad to include them in the newsletter; send the job link to [email protected].

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 [email protected].

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.