A washcloth, a canceled flight, and the difference between an itinerary and knowing what to actually pay attention to.
I've spent a lot of years traveling, and if there's one thing that time teaches you, it's that a trip isn't made or broken by the big things. It's the small ones. You can read a hundred reviews about a hotel and still miss the one detail that would have actually mattered to you. Traveling for a living actually teaches you to notice those things — because there's no one else to catch it for you.
The first time I walked into Bellevue Serene in Sorrento, I was floored. You come up through this wisteria-draped entryway and it just sets the whole tone before you've even checked in. I had my arrival aperitif, got escorted up to my room after a long travel day, and went to freshen up — looking around the bathroom, rummaging around the linens looking for a simple washcloth but all I found were these long linen hand towels, nothing close to what we're used to at home. Such a small thing. But after a full day of travel, it's the thing you actually notice. At the end of every day on that trip, washing my face with this long linen towel just wasn't the same, it was a small detail but I noticed.
Every review of that hotel will tell you it's stunning. None of them will tell you to pack your own washcloth. Now, when my clients head to Sorrento, that's exactly what I tell them — and I've had people write back just to thank me for thinking of something that small. That's the art of it. Knowing what to actually look for, and caring enough to look.
Here's the other side of that same instinct. I had clients island-hopping in Hawaii — Oahu into Maui, with their first stop meant to be Hana, reachable by a small regional plane out of the Maui airport. Except the airline decided, last minute, to just cancel the flight. My clients get to the counter and hear, "that flight's not running anymore." They called me, understandably a little rattled.
In under thirty minutes I had a private driver — someone I'd built a real relationship with over several trips to Maui — willing to drop everything, pick them up, and take his time getting them there, stopping at waterfalls along the way. Views they never would have seen if that flight had just taken off on schedule. What looked like a disaster at the ticket counter turned into one of the best parts of their trip.
I tell clients this all the time now: not everything that goes wrong is actually wrong.
AI can churn out an itinerary in seconds — the flights, the hotel names, a tidy list of things to do. What it can't give you is the instinct to notice the washcloth, to know a driver by name, to see an opportunity inside a canceled flight. That's not information. That's experience, built one trip at a time, including the ones you take completely on your own. An itinerary tells you where to go. Experience tells you how to actually be there.
If you're planning something and want that kind of eye on it, I'd love to hear where you're headed.
