Orange Chicken, OTA Creep, and a Hotel from 1890

October 21, 2025

Aloha !

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 [email protected]. 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?

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, Hampton Inn Kapolei), 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 [email protected]. 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 [email protected]

First-come, first-served.

Join top hotel execs for a full day of real talk, trends, and industry insight.

*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].

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 [email protected], 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.