Marvel Villains, Parking Lot Luxury, and AI Airport Slop

May 03, 2026

Aloha !

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.

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! 😉😉

The Rise of AI-Planned Travel
-Sponsored-

Travel planning is entering a new era. Guests are no longer just searching; they are asking AI to decide where to stay, what to book, and when to book it. That shift has major implications for hotels.

TakeUp’s new research report, The Rise of AI-Planned Travel in 2026, breaks down what is changing and what operators can do about it. From how AI tools choose which properties to recommend, to why OTAs are gaining an edge in AI-driven discovery, this report gives hoteliers a clear view of what is coming next.

If you want your property to stay on the shortlist as booking behavior evolves, this is a must-read.

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

*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].

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 [email protected], 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.