AI vs. Intuition: What Nearly Three Decades In Travel Taught Me That No Algorithm Knows.

There's a lot of talk right now about AI planning your next trip. And honestly? It can — it can build you an itinerary in seconds, suggest hotels, even guess at a budget. I'm not here to argue with that.

I've been in this industry since 1997 — starting as a travel agent, spending ten years exploring other parts of the industry, and running my own business for the sixteen years since. In that time, I've learned that planning a trip and actually experiencing it the way you hoped are two very different things — and a lot of that gap comes down to how well someone understands what you actually want before a single flight is booked.

AI can build an itinerary. It can't read a room.

It doesn't know which resort quietly upgrades honeymooners, or which one is mid-renovation right when you'd be there. It hasn't sat across from a client and figured out that what they're describing as a "relaxing trip" is actually code for "I need to not think about anything for ten days." That's not data. That's years of paying attention. And it definitely can't reschedule your life at short notice.

This year alone, I've spent more hours than I can count helping clients adjust plans as things shifted in the Middle East — flights rebooked, routes reworked, itineraries rebuilt around news that was still unfolding. Nobody wants to be dealing with that on short notice. But when it happens, you want someone who's done it before, who knows which airlines actually pick up the phone, and who isn't panicking right along with you. It starts with asking the right questions.

When I started out, qualifying a client was simple: destination, budget, past trips. Those questions still matter — but they're really just the opening. The real work is intuition — listening for what someone isn't saying outright. Two clients can ask for the same destination and the same budget and want completely different trips. One question can lead somewhere unexpected, and following it is often what separates a good trip from the trip someone still talks about years later. That's not something you can prompt your way into. It's built one conversation at a time.

So where does that leave AI?

Honestly — I think it's a great starting point. Use it to daydream, to get inspired, to see what's out there. But somewhere between "wouldn't it be nice to go to Portugal" and actually being in Portugal with the right hotel, the right guide, and a backup plan if something goes sideways, that's where nearly thirty years of doing this for a living still matters.

That's the gap I fill. Not instead of the tools — alongside them.

If you're dreaming about your next trip, I'd love to hear about it. Hit reply on the newsletter or get in touch — let's figure out where you're headed.