A NEWSLETTER FROM Pryority Travel

 

The light hits the terrace at golden hour. The views are legitimately stunning. And if you ask an AI to find you the best dinner spot on the island, there's a good chance it ends up on your itinerary.

 

My client found it exactly that way. She came to our call with a short list of restaurants she'd researched, and this one was near the top. I told her I'd check with some contacts on the ground before we finalized anything.

 

The response I got back was polite but direct: that place is for influencers. People go to take photos in front of the sunset, not to eat. If you want an actual Sardinian meal, I know where to take you.

 

She went with my recommendation and she never forgot the Porceddu and Pane Carasau.
 

This is not a story about AI being wrong. It's a story about what AI is optimizing for….and what it isn't.

Henna and I have been going to SXSW for a few years, Henna has even spoken there twice! Each trip, our schedule is packed, but one talk we never miss is Amy Webb's annual tech trends forecast. Webb is a futurist who runs the Future Today Institute, and she has a gift for making complex technological shifts feel both urgent and understandable.

 

Her 2026 talk was terrifying to say the least. We are moving, she argues, from assistive AI, the kind that helps you search, suggests options, makes things faster…to DEEP agentic AI. Systems that don't wait for you to ask. They act on your behalf, negotiate, compare, and book at machine speed. The internet is becoming less of a search tool and more of an autonomous agent working in the background of your life.

 

How will this affect travel?  Well, when an AI agent is evaluating your options, it does what any algorithm does: it optimizes for what's indexed. Price. Room size. Review volume. Star rating. It is extraordinarily good at finding the restaurant with the most photos of sunsets.

 

What it cannot find is the place the locals actually go.

 

There's a term emerging in the luxury space for what happens next: anti-optimization. The best hotels, the most exclusive properties…they are beginning to deliberately stay off the grid. Not because they're behind the times. Because their value depends on not being reduced to a spreadsheet row.

 

Here's how this plays out in real life - When a client books a family trip to London, I don't just confirm the hotel and send a voucher. I brief the team at the One&Only (for example) on everything I know about that family. Who the kids are. What they care about. What this trip means to them.

 

For one family heading to their first Premier League match, the team at 1 Hotel Mayfair took that briefing and built a scavenger hunt. Clues hidden around London, each one leading them closer to the stadium. The kids were screaming before they even got to their seats.

 

The Ritz-Carlton Grand Cayman operates the same way. When I have clients there, experiences get arranged that you won't find on any website. They require a conversation, context, and trust between people who know each other.

If you want to watch Amy Webb's full 2026 SXSW talk, it's worth an hour of your time. You can find it here.

 

The future is splitting. There is commodity travel, which AI will book faster and cheaper than any human ever could. And there is a tier above that, defined not by price but by access…to relationships, to properties that don't advertise, to the kind of personalization that requires someone to actually pick up the phone.

 

P.S. If you've ever let an algorithm pick a restaurant for you and regretted it, you already understand the argument. Reply and tell me where it went wrong. I have a feeling I'll hear from a few of you!

A FEW DETOURS WORTH TAKING

If you’re new here, welcome. I’m Ian, a travel advisor who helps people design trips that

feel personal, thoughtful, and easy from start to finish. I’m really glad you’re here, and I

hope you’ll stick around for destination ideas, inspiration, and stories from the road in

the weeks ahead.