Planning a group trip is complicated, but a multigenerational family trip can be even worse. You're trying to plan for different people, interests, and needs; throw in a variety of ages, and it’s too much to juggle. Usually, grandparents want flexibility and time together as a family. Teens care about wifi and adventure, rather than museums and culture. Mom and Dad might want some time apart, just by themselves. And all your six-year-old cares about is the pool.
No one gets everything they want on a trip like this, but there's a little magic in good trip design: it balances needs and keeps the overall flow working, even when someone isn't getting exactly what they want at any given moment. If you're the organizer (or, even more importantly, the person paying for the trip), read on for our guidelines and recommendations for how to go about getting this trip out of the group chat.
Pick a point person
If one person is paying for the trip, they get the ultimate veto. If it's going to be split, you still need someone willing and able to take the lead. If you're working with an advisor, they'll coordinate directly with your point person; otherwise, that person should handle the hotel and the big planning blocks, and delegate the rest.
Before you book anything, discuss
Get everyone together over dinner or on a quick call to talk about what matters most to them. Priorities, priorities, priorities. Give everyone a chance to be heard, but that doesn't mean you can grant every wish.
Get all expectations on the table: discuss deal-breakers, budget, date restrictions, and destinations that are a no-go. What's comfortable for one family member might not be realistic for another. Mention it up front so your group doesn't go too far down a path before realizing your plans won't work for everyone.
Discuss budget and who pays for what. In some families, expenses are divided between the households; in others, money is pooled for shared costs and families use an app like Splitwise to settle up. Either method works.
Simplify your plans
For groups, we recommend no more than two destinations in a week. It's one thing to pack up and move every couple of nights when it's just a couple of you on the go. It's another when you've got to coordinate kids and other family members, and no one wants to feel like they're living out of a suitcase. If you're traveling with very young kids, choose a home base that’s located somewhere convenient to give people flexibility to do what they want during the day: maybe grandma and grandpa go to the market while the kids and the dads go zip lining and the moms stay back at the spa, and then everyone meets up in the evening for dinner.
Don't overfill your schedule, and don’t force it
Plan each day around one activity that everyone takes part in: a boat trip, a guided walk, or dinner somewhere with a view. Don't schedule every minute, and don't expect everyone to want to do the same thing at the same time. If interests clash, or a couple of people want to do something no one else is into, split up and do it. It's not that serious. Not everyone needs to go snorkeling, and the kids might not want to be dragged out shopping.
Accept that some group members may need time alone or apart from the group. It's okay for someone to go for a walk by themselves, spend an afternoon reading a book, or nap while the rest of the group is out for the day.
A little room to yourselves
Six bedrooms can look like more than enough until you’re all sharing a bathroom. Walk through the floor plan and figure out if it really works for you: twin beds for the cousins, a nearby bedroom for the toddler, a separate suite for whoever needs the space.
At a hotel, connecting rooms have an interior door; adjoining rooms may just be next to one another. Connecting rooms are rare in some corners of the world, so be prepared to keep the whole family in the same room if your kids are too young to sleep in their own room.
Frequently asked questions
How long should a multigenerational trip be?
Most of our multigenerational groups stay a week to ten days, with one home base where possible, or two at most. Staying put for four or five nights at a time, rather than moving every couple of days, lets the group settle into a routine instead of living out of suitcases.
What if some family members want a more active or adventurous trip than others?
Choose shared activities everyone can enjoy, and let the more active family members organize their own extra excursions during the built-in free time, or if you have an advisor, let them sort it out. No one needs to miss out entirely to keep up with the group, and nobody has to be dragged along on a hike when they'd rather be reading by the pool.
Do we need separate arrangements for different households?
Not really, but it's possible to have separate sleeping areas, connecting rooms, or a second, smaller unit on the same property, so people can close a door at the end of the day. On trips longer than a week, privacy matters more than people expect going in. Private bedrooms and bathrooms keep everyone happier than being crowded together the whole time.
It's not realistic to expect a perfect itinerary that keeps everyone amused every moment. Instead, set aside enough time for shared experiences and meals, and balance that with individual time so people can do their own thing and get the most out of the trip. At Osaviva, we've planned multigenerational family trips to Costa Rica, the Galápagos, Peru, Mexico, and the Caribbean, and the trips people love most are the ones where everyone experiences something new together without feeling oversubscribed. If you get in touch, we'd love to discuss which of our destinations would suit your family.