Multi-Generational Travel: A Few Notes from 17 Years

A few times a year, a client calls and tells me they want to take the whole family — parents, grown children, grandkids, sometimes a sibling and her family too. They have a milestone in mind, or they have reached a year where it feels important. They want to know if I can help them make it work.

I always say yes, with one caveat: this is the kind of trip that asks for a little more upfront thinking than most. After almost two decades of planning these, here are the things I find myself coming back to.

Start with the Slowest Traveler in the Group

Every multi-generational trip has someone who sets the actual pace, whether the rest of the family realizes it or not. Sometimes it is the grandparent with a knee that does not love long walks. Sometimes it is the toddler who needs a real nap by three. Sometimes it is the teenager who quietly hates being marched through churches.

If you build the itinerary around the most flexible person, the trip works for them and exhausts everyone else. If you build it around the least flexible — gently, without making a fuss about it — the trip works for everyone. The strong walkers can always do more on their own. The strong walkers cannot, however, conjure energy back into a tired six-year-old.

The Quiet Power of a Home Base

For families of more than six or seven, I almost always recommend a single property for the whole stay rather than a multi-stop itinerary. A villa in Tuscany. A larger suite arrangement on a cruise. A hotel with adjoining rooms in one resort town. The trip becomes about the place rather than the moving.

A home base also solves the constant low-grade negotiation that exhausts most family trips: what time is breakfast, where do we meet, how do we get back. Everyone goes off and returns to the same kitchen at the end of the day.

Build in a Real Day Off

I have seen too many family itineraries with seven days of tightly planned activity and one optional rest day that nobody actually takes. The rest day matters more than the tour days. It is the day grandma reads on the terrace and the kids find the pool and the parents take a walk together for the first time in a year.

When I plan these trips, I block one day in three with nothing on the calendar. Not free time before dinner. A whole day. Most families come back and tell me it was the day they remember best.

One Meal a Day, Together

The most successful multi-generational trips I have planned share a small habit: dinner is together every night, but lunch is whatever each pod wants. The teenagers go off with their cousins. The grandparents take a long, quiet midday meal at the hotel. The parents take the kids to a park for picnic food. Then everyone reconvenes at the same long table at seven.

This rhythm gives the introverts in the group an off-valve, and gives the extroverts the social glue they came for. Both groups end up happier than they would in a forced-march schedule of every meal together.

The Logistics Worth Outsourcing

Three things, in particular, are worth handing to an advisor on a family trip: the airport-to-hotel transfers (especially for the older travelers), the dinner reservations (because no one wants to argue over a phone in a foreign language at five in the afternoon), and any activity that requires precise coordination across multiple groups arriving from different directions.

I will gladly let a family plan their own walking tours. The thing they will be most grateful to have outsourced is the moment a flight lands at midnight and a tired group of nine needs to be at the right hotel an hour later, with luggage, in two vehicles.

The trips families remember are rarely the most ambitious ones. They are the ones where everyone slept well, ate one good meal a day together, and had room enough in the schedule for the unplanned moments to happen. The itinerary is just the frame. The trip is the people inside it.