I Let an Algorithm Plan My Road Trip and Had the Most Peaceful Week of My Life
What to Buy
Hotel investment has never lacked momentum. What feels different today is not the occasional downturn itself, but the widening disconnect between how risk has traditionally been assessed and where it is quietly accumulating.
Capital markets are not stepping away from hospitality. They are becoming far more deliberate about what they are willing to underwrite and, just as importantly, why.
Familiar indicators such as scale, brand affiliation and historical performance still matter, but they no longer guarantee resilience on their own. Increasingly, investors are paying attention to signals that are harder to quantify: leadership judgment, cultural relevance, decision agility and intelligence readiness.
A Changing Landscape
The most consequential shift shaping hotel performance today is not demographic in the narrow sense, but behavioral. High-spend travelers across younger generations are more intentional. They value coherence over spectacle. They plan further ahead, stay longer, travel with a clearer purpose and disengage quickly from brands that feel repetitive or hollow. What they reward is alignment between experience, price, service philosophy and narrative.
Assets designed around yesterday’s loyalty logic gradually lose pricing power. Traditional, points-based programs are giving way to experience-led, in-stay recognition models, yet many portfolios still rely on discounting to fill short-term gaps.
Over time, this erodes yield and performance. Marketing costs rise, while organic advocacy and channel efficiency weaken. Digital marketing is still too often treated as a cost center rather than a precision tool. By contrast, hotels with a clear value-creation mindset where concept, experience and operating philosophy are tightly aligned demonstrate more stable RevPAR performance and lower rebranding risk across cycles.
The AI Blind Spot
Much of the industry’s conversation around artificial intelligence remains focused on tools rather than judgment. Yet the question capital is asking is simpler and more demanding: Is this asset capable of making better decisions under pressure? Technology layered onto outdated decision frameworks tends to amplify inefficiency. Data multiplies, but insight does not. Personalization becomes noisy.
True AI-readiness is architectural. It requires clean data foundations, integrated systems and intellectually grounded leadership that knows when to trust intelligence and when to intervene. Assets that achieve this reduce volatility through better forecasting, more confident pricing and faster operational response.
Assessing Leadership
A similar repricing is taking place around leadership risk. Investors are no longer underwriting assets alone; they are underwriting decision-makers. Beyond brand strength, questions around talent retention, learning culture and leadership continuity are increasingly part of the investment conversation. Traditional, scale-driven management structures often struggle as complexity grows. Accountability diffuses, decision cycles slow and downside exposure increases. In contrast, founder-led or tightly aligned operating platforms (free of silos and anchored in clear authority) move faster, preserve intent and manage risk proactively rather than defensively. This distinction is becoming especially relevant in long-hold strategies.
New Opportunities, New Judgment
These shifts are also reshaping where capital is flowing. Investment momentum is building around experiential and niche travel segments, not as trends, but as structural demand responses. Sports tourism tied to global events such as the 2026 FIFA World Cup is driving destination-level investment focused on cultural and fan-centric ecosystems. IP-driven travel, from film and media locations to music and cultural movements, is giving rise to immersive, branded journeys. Wellness- and nature-led hospitality from quiet retreats to integrated wellness ecosystems is expanding as travelers seek restoration, authenticity and space.
At the same time, seasonality is blurring. Off-peak and midweek travel is rising as remote work enables longer, more flexible stays. Personalization expectations are increasing, with travelers seeking clear value tiers and experiences tailored to intent rather than status. Even cruising, once considered peripheral for younger demographics, is seeing renewed growth as formats evolve and experiences become more curated.
What unites these patterns is not novelty, but discernment. Scale itself is no longer a hedge. Large, undifferentiated portfolios face margin pressure as expectations fragment and exits become timing-dependent rather than desirability-driven. Meanwhile, smaller assets with strong identity, flexible models and a deep understanding of their target market are proving more liquid than expected precisely because they are harder to replicate.
What is emerging is a quieter, more disciplined definition of investable hospitality. Durable assets are not those chasing every trend, but those designed with foresight. They anticipate behavioral shifts, use technology to sharpen judgment rather than replace it and are led by individuals who understand that trust from guests and investors alike is the most valuable currency in the system.
The future of hotel investment will be written by those who know when comfort stops protecting value and have the restraint to build differently.
If you’d told me I’d watch Eric Ripert plating pristine bites on the beach, Stephanie Izard stopping to chat at every table after cooking a private dinner for hundreds of guests, and José Andrés scuba diving for lionfish—then handing me a bowl of ceviche he’d just made from the catch on the dive boat—I’d have assumed you were pitching a food-nerd fever dream.
Instead, it’s Cayman Cookout: a luxury culinary festival hosted by The Ritz-Carlton, Grand Cayman on Seven Mile Beach. And while I absolutely came for the food, what wowed me most was seeing some of the world’s most famous chefs genuinely interact with guests.
This isn’t a convention-center food festival where you’re squinting at a stage from row 47. Your morning might start with room-service breakfast on your balcony, or with a plated caviar breakfast by chefs Philippe Haddad and Bernard Guillas. Then you head down to José Andrés’ famous Paella Showcase in a beach pavilion, where his team tends giant pans while he keeps the crowd in stitches with stories and sharp, good-natured jabs at the other chefs in attendance. The headlining late-morning event, though, is the signature Bon Vivant Sunday Brunch, where young Caymanian chefs and hospitality talent get their moment in the spotlight, and the longest line in the room, fittingly, is for more caviar.
By afternoon, you’re bouncing between more chef demonstrations and events, like a rum-and-cigar poolside party or Grown in Cayman on the Great Lawn, hosted by Andrew Zimmern and showcasing dishes by local Caymanian chefs. The Beach Bash whisks guests away by catamaran to Rum Point, where you can kick off your shoes and wander through the sand from station to station for plates of what the chefs are firing up right in front of you.
And at night, the festival leans all the way into its beach-party side. Barefoot BBQ on Seven Mile Beach is exactly what it sounds like: stations run by big-name chefs, toes in the sand, waves in the background until the DJ’s beat takes over. There’s a late-night poolside soirée and a jazz lounge, where at both you’ll spot chefs and guests dancing in the same crowd.
The surprise, though, is how approachable everyone is. One moment they’re leading a packed demo, taking audience questions, or cooking at their station; the rest of the time they’re wandering the property, chatting with guests, playing pétanque, or stopping for questions and selfies. If you’ve ever wanted cooking tips or life insights from your culinary heroes, this is your chance to get them face-to-face instead of shouting into the Instagram void.
It’s not just the food, either. Cayman Cookout attracts some of the world’s top bartenders and drinks pros, so your day might include a tiki cocktail session with Kate Gerwin, a beachfront champagne tasting hosted by sommelier Aldo Sohm, and a perfectly stirred cocktail by Charles Joly. It all feels like the most fun night out, just with world-class food and drinks.
Eric Ripert dreamed up the concept nearly two decades ago, after opening Blue at The Ritz-Carlton, Grand Cayman, the highly acclaimed Forbes Five-Star and AAA Five Diamond-rated restaurant. Since then, Cayman Cookout has grown into an internationally recognized festival while staying true to its roots as an intimate culinary event.
When I asked Ripert about his vision for Cookout’s future, he said he wants to continue bringing in new ideas and talent from around the world.
“Cayman Cookout evolves like that,” he said. “It’s never the same, because the food is not the same, the cocktails are not the same, and the talents are different, with different personalities. But the DJ is always the same,” he laughed. And for good reason: that DJ had masses of people on their feet dancing after very full evening meals.
None of this is casual on the wallet, though. Staying at The Ritz-Carlton and stacking multiple ticketed events is a true splurge, the kind people save for alongside big concerts, safaris, or once-in-a-lifetime trips. But if you’re the kind of traveler who plans vacations around restaurants, who follows chefs the way other people follow actors and musicians, Cayman Cookout belongs squarely on your bucket list.
Because sometimes, meeting your heroes looks like the best ceviche you’ve ever had, dancing in the sand with fellow food-lovers to “Pink Pony Club,” and a chef you’ve only ever seen on TV leaning in to answer your question like you’ve been friends for years.
“The number one thing we’ve seen to get deals done is that there needs to be a lever or a real business plan and an opportunity to make something change,” he said. “Whether that’s a change of the flag or whether that’s bringing in some sort of expansion or something to do that really changes it from A to B. You can’t just say, ‘I’m going to paint the pig and then I’m going to sell it to the next guy.’ You really have to figure out a way to make something interesting.”
Michels was a panelist on the “Opportunities: Evaluating market conditions” panel on the first day of the ALIS by Northstar conference at the JW Marriott/Ritz-Carlton Los Angeles L.A. Live in Los Angeles. The panel included Kevin Dingle, chief development officer at Denver-based Stonebridge; Michael Harper, president, hotel lending, credit at Peachtree Group; Brian Patrick Murphy, CEO of BPM & Company and Valerie McCormick, senior vice president of development, portfolio relations & owner relations for Aimbridge. John Fareed, global chairman of Horwath HTL, served as moderator.
Michels said the debt space has become more crowded of late, which can benefit owners.
“There are a lot of players in that market. What’s happened over the last 12 months, to the benefit of a lot of hotel owners, is that it used to be primarily post-COVID debt funds that were your primary form of lenders out there,” he said. “Now I think with the performance of a lot of hotels, CMBS is a very viable option. We’ve started to see the banks come back and we’ve also started to see life insurance companies enter the space again.”
That level of debt competition is going to drive down spreads and yields and could increasingly make construction financing easier to pencil, Michels said.
“That will ultimately lead to hopefully more lenders pushing into the construction space in order to get the yields they need to put out capital,” he said. “So that’s one area we’re keeping an eye on, in terms of it still needs to make sense from a development perspective and a low yield cost... But it is interesting that you may have more capital sources out there to finance some of these construction deals.”
Using CPACE in different ways
CPACE financing has become more common, too, Harper said.“Historically, it’s been thought of as a new development tool, when there’s not as much debt capital out there,” he said. “It’s a long-duration, low-cost of capital tool that works as a tax assessment, rather than pure debt.”
What’s new, Harper said, is the different ways CPACE is now being used in the capital stack.
“What’s been most interesting over the last, really, four years since COVID, is you can retroactively apply CPACE. Over the last five years, everyone’s talked about rescue capital and preferred equity… and that’s been a really difficult thing to execute on, because nobody wants to stomach the pricing.
“CPACE can also be applied retroactively, and it’s been a great rescue tool, because what you might do is fund against improvements that were done in the last three years in a hotel that hasn’t ramped [up yet] and you are paying down your senior debt and funding some interest reserve… Everyone’s always thought of it as a development tool, but it’s actually worked really well as a rescue capital.”
Bullish on full-service
When the question came up about whether big box, full-service hotels are dead, McCormick said that while the rules have changed, there is still a huge need in that space.“I don’t think they’re dead at all. You’re going to have a lot of downtown markets and higher barrier-to-entry markets,” she said. “When you’re looking at those suburban boxes, what we’ve heard is, and we were having a conversation earlier today about this, is you really just can’t have this abundant meeting space in suburban markets because there’s just dwindling demand.
“People aren’t traveling the same, and there aren’t as many large corporate groups that are traveling in the same way,” she said. “So you really have to get creative and make sure that there is revenue coming into those specific assets… it has to be a higher barrier-to-entry and it has to have multiple demand drivers.”
Michels said he actually loves the idea of buying big box hotels right now because of the steep discount to replacement cost you can get.
“There’s a really interesting angle. We talked about basis. You can buy some of these hotels in major markets at a quarter of the cost to build today,” he said. “They’re not going to build anytime soon, not unless you have big tax incentives with a city that wants to incentivize a convention center hotel or something like that. You’re not going to see new supply in these markets. So there’s a really interesting story around: can you buy these things at a great number?”
The soft-brand debate
Discussion on the panel eventually focused on (as it usually does) on there being too many brands and the newer prevalence of more soft brands to help lure independents into big brand company’s loyalty programs.Dingle noted that he and Stonebridge are fans.
“We love soft brands, even though there are too many of them. But it’s certainly just where things are directionally going with the Millennials and the demographics,” he said. “The nice thing about soft brands, too, is that there’s more flexibility on the renovation. Does it reduce the cost of the room? It definitely can. F&B requirements can be different and less if you don’t want to spend as much. You’ve got a lot of different options.”
Martin said the decisions on soft brands can vary dramatically from market to market.
“We love to talk about this industry in these nice, big brushstrokes, like it’s a watercolor and it’s not. We’re a mosaic, and it’s the micro that really defines it,” he said. “What may be a good idea for a soft brand in market A or B, because of the way the demand base functions in that market, would be suicide in market C.”
Martin said certain markets often dictate which brand is most important and what is essential to the client base.“It’s being able to regulate the demand side to maximize revenue. There is no simple answer to that question,” he said. “There are markets where the person has to be there… there’s an expansion, a project plan or a hospital. They have to be there. That’s where your stronger brands tend to do better. Because I’m going there. I have to be there anyway, I’m going to stay at Brand X, because I’m going to get my points… Then there are the markets where people want to be there, and in those markets, that brand value, which 30 years ago was still paramount, has waned substantially.”
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