Friends who travel well.
How I choose who comes on the trip, and why it matters more than the destination.
By Brandi Harris · Autumn 2026I’ve planned trips to beautiful places that felt long, and trips to ordinary places I still talk about. The difference was almost always who came. After enough of both, I stopped choosing the destination first. Now I choose the people, and the trip follows.
Travelling well isn’t the same as being fun
Some of my favourite people are wonderful at dinner and difficult on a trip. That’s not a judgement. Travel asks for different things: flexibility, patience with delays, and being honest about what you want from the day. Here’s what I look for.
They say what they want. “I’d love a slow morning” is a gift. Silent resentment by day three is not.
They’re fine apart. The best group trips have time together and time alone, and nobody takes the alone part personally.
They’re easy about money. They’re clear about budget up front, and they don’t keep score at dinner.
They match the pace. Not identical, but compatible. An early riser and a late sleeper can share a villa. Two very different trip styles usually can’t.
“The right people can save an average hotel. The wrong ones can ruin a perfect one.”
The conversation before you book
This is the one that fixed it for me. Before anyone books anything, we talk about three things: budget, pace, and one thing each person wants from the trip. It takes twenty minutes and saves days of friction. It’s also why I built the travel persona quiz: it gives a group a shared language for how each person likes to travel.
If one friend is a Leisurist who wants the lounge chair and another is an Adventurist who wants the 6am hike, that’s fine. You just plan for it: a base that suits both, a couple of shared moments, and freedom the rest of the time.
Plan the shared moments, not every moment
I plan two or three things the whole group does together: an arrival dinner, one special experience, and a last-night meal. Everything else is optional. People relax when they know what’s expected of them, and they enjoy the shared parts more when they chose to be there.
Agree a budget range, out loud.
Each person names one thing they want from the trip.
Choose a base that works for the different paces.
Plan two or three shared moments; leave the rest open.
Decide how you’ll split costs before the first bill.
When I plan group trips for clients, this is where I start. Who’s coming matters more than where you’re going, and getting it right is the difference between a trip you survive and one you repeat.
— Bee