Have you ever been to a really great restaurant?
Before they hand you the menu, before they mention the specials, before they even take your drink order — they ask if anyone has allergies.
Why? Because that answer shapes everything that comes next.
Travel planning works the same way. Most advisors plan the way the travel industry packages things — built around places. The destination, the hotel, the must-do list. That works beautifully for plenty of trips.
But if you’re planning the kind of trip that revolves around the people going — a family reunion, a milestone celebration, a girlfriends’ getaway, a heritage trip — that approach is backwards. The first question isn’t where are we going? It’s who’s coming, and what’s bringing everyone together? A trip for four college roommates is a completely different trip than a 70th birthday with grandparents and toddlers — even if they’re going to the same place.
When you finally get to spend time with your favorite people, the destination is less important.
Here’s what I’ve learned doing this for almost 30 years.
People are not all wired the same way.
Some want to understand a place deeply — the history, the architecture, the why-is-this-here? Some need to keep moving — hiking, biking, kayaking. Some want to feel a place through their senses and a conversation with a local at a café. And some people just want to lie by a pool and forget the world exists.
A good trip has room for all four. When it’s planned around just one person — the trip organizer, say — you get the rest of the group coming home feeling like they need a vacation from their vacation.
When you start with the people, a hotel makes less sense.
Hotels separate people. Different rooms, different floors. And then there’s mealtime. Every meal, someone has to organize the troops. Can we get a reservation? Can we all sit together? Can we actually hear each other across the table? Before you know it, you’re spending more time playing camp counselor than being together.
In contrast, villas bring people together. A private pool, a table that seats everyone, a kitchen everyone wanders through all day. That’s where the bonding actually happens — not on an itinerary, but in the kitchen at 10pm because your teenage nephew wandered in for a snack and somehow ended up telling his grandmother his entire dating history.
But not every villa delivers on that promise — and the photos don’t tell you which ones do.
You don’t want to be the family pulling up to your pricey Tuscan villa to find 53 steep steps between Grandma and the front door. (True story — told to me by another advisor.)
Look for villas that have been inspected and vetted by a human. Not just listed. The layout, the accessibility, whether the kitchen is actually the heart of the house or just a room with a stove — that’s the difference between a villa that looks right online and one that works once everyone arrives.
And look for ones that include concierge support. Not a number to call if something breaks — someone who’s actually there.
You know the expression “to know a guy”?
That’s really what a great concierge is. Not a hotel concierge handing you a map. Someone local who knows the chef who’ll cook you dinner at the villa, the driver who shows up on time, the beach nobody puts in the guidebooks. Someone who can fix a problem at 9pm on a Saturday — quietly, before it becomes the story.
My extended family did a heritage trip to Sicily once — tracing my mother-in-law’s roots. Our concierge connected us with a guide who knew the mayor of the town. The mayor spent the entire day with us, gave us the VIP tour, and introduced us to people who showed us where family members had lived.
We went to find where we came from. We left feeling like we were part of something still alive.
Nobody books that experience on Expedia. Our concierge made it possible.
The whole point is the feeling, not just the place.
I remember being in the Galápagos, snorkeling with sea lions. One swam right up to me underwater, just hovering there, looking me in the eye. Then it darted off, swam over to my wife, and jumped clean over her — like something out of a Flipper movie. Everyone on the beach burst into applause. We looked at each other like, did that really just happen?
That’s what I want for you. Not just a nice place to stay. A moment that takes you out of your day-to-day — where you’re just there, fully in it, fully alive — shared with your favorite people.
One more thing worth knowing.
I was once contacted by a father planning his son’s destination wedding. Big budget, beautiful location, very clear vision. When I suggested asking his wife and son what they wanted, he said: “I’m paying for it. They’ll do it my way.”
I passed on that one. That mindset is almost a guarantee of failure — and not a trip I want to help build.
Travel advisors are wonderful. But just like there are different kinds of doctors and lawyers, there are different kinds of travel advisors. You want to make sure you pick the right one for the trip you’re hoping for.
If you’re planning one of these trips — a reunion, a heritage trip, a milestone you’ve been waiting years for — that’s exactly the kind of trip I love working on.
I’d love to hear what you’re celebrating.
