There’s a particular kind of magic in gathering three generations in one beautiful place, with grandparents, parents, and kids all making memories at the same table. But anyone who’s tried it knows the other truth: a trip that has to delight a seven-year-old, a teenager, a busy parent, and a grandparent all at once is one of the hardest to plan. It’s also, hands down, my favorite kind of trip to design, and the way my own family loves to travel.
So if you’re wondering how to plan a multigenerational trip that everyone genuinely enjoys (not just tolerates), here’s the approach I use with my clients and my own kin.
Start with the “why”
Every great multigenerational trip has a reason behind it: a milestone birthday, a big anniversary, a graduation, a reunion, or simply the realization that everyone’s finally in a season where you can all get away together. Naming that “why” up front is more than sentimental: it becomes your north star when the planning gets complicated and opinions start to differ. When the whole trip flows from one shared purpose, the little disagreements about logistics tend to melt away.
Choose a destination that works for every age
The best multigenerational destinations share a few quiet traits: they’re easy to get around, they offer a real range of things to do (a calm beach for little ones, culture for the grandparents, a bit of adventure for the teens), and they aren’t so spread out that half your trip is spent in the car. Places like the Costa Brava, Italy, Portugal, and Costa Rica shine because they layer relaxation and discovery in one place. (If you want to see what this looks like in practice, here’s how our family did the Costa Brava with kids.)
Get the lodging exactly right: it can make or break the trip
More than anything else, where you stay determines how a multigenerational trip feels. The magic ingredient is space to be together and space to retreat. In practice, that means a villa, a two-bedroom suite, or connecting rooms, plus a shared common area where everyone naturally gathers at the end of the day.
I’ve seen this firsthand. On a recent family trip, a two-bedroom suite meant the kids had their own space while we were all still “home” together; at another hotel, a family room with a couple of bunk beds was an instant hit. Small things like a kitchen, a pool, and a living room big enough to spread out in do far more for group harmony than any five-star rating ever will.
Balance together-time and alone-time
The fastest way to fray a family trip is to schedule every single minute together. The trick is to build the day around one anchor, like a shared breakfast or one group outing, and then let the rest of the hours breathe. Grandparents might want a slow morning with coffee; the teens want to wander on their own; parents might slip away for a quiet dinner. Protecting that freedom is exactly what makes the together-time feel special instead of obligatory.
Plan around different paces and needs
A thoughtful multigenerational itinerary quietly accounts for everyone: gentler pacing and step-free options for grandparents, downtime and snacks for the youngest travelers, and a little independence for the teens. It’s rarely about doing more. It’s about sequencing the day so that nobody is exhausted, overstimulated, or bored at the same moment. That invisible choreography is most of the work, and it’s what makes the difference between a good trip and a great one.
Have the money conversation early
Who pays for what is the least romantic part of family travel, and it’s the most important thing to settle before you go. Decide early whether the trip is split, hosted, or à la carte, and put it in writing so there are no awkward moments at checkout. This is also one place where having a travel advisor quietly earns its keep: I can act as the neutral coordinator, so no one at the family dinner table has to be the “organizer” or the “banker.”
Let someone else carry the details
Here’s the honest truth about family trips: one person usually ends up doing all the planning, and quietly wishing they weren’t. When you hand the logistics to an advisor, that person finally gets to just be on vacation with everyone else. I take care of the research, the bookings, the reservations, and the just-in-case moments, and I layer in perks most families can’t get on their own, from room upgrades to daily breakfast to resort credits, through Virtuoso. My whole job is to handle every detail so your family can focus on the one thing that actually matters: reconnecting.
Ready to plan yours?
A multigenerational trip is one of the most meaningful gifts you can give the people you love: time, together, somewhere beautiful, with none of the stress. If you’re dreaming of gathering your family, schedule a consult and let’s design a trip they’ll be talking about for years.
XOXO~
Shannon
