Multigenerational travel has only one truly difficult part, and it isn’t the flights or the budget or the packing. It’s that a four-year-old and a seventy-four-year-old want completely different things from a single day (shocking, I know!), and you are trying to create one trip that sends everybody home happy. Grandma wants the museum and a slow lunch. The teenager wants the wi-fi password and to be somewhere cool and hopping. The toddler wants a puddle and a slide (and snacks. Well, we ALL want snacks). You want, oh, maybe a good cup of coffee, and fifteen minutes to explore!
Good news: it’s absolutely doable. We’ve been figuring this out as a family for years (with all the ages and stages that implies), and the trips where three generations travel together are the ones we treasure MOST! The kids get their grandparents in a way a holiday gathering never quite delivers. On a multigenerational trip, everyone gets the good stuff, the actual time, the shared table, the inside jokes that only form during shared experiences.
Here’s your guide: the tips that keep a multigenerational trip from turning into a logistical and scheduling headache, drawn from years of traveling with the people I love most.
Start with the trip everyone can actually do
Before you fall for a destination, take a clear-eyed look at your group. A trip that thrills the teenagers but leaves Grandpa parked in a hotel lobby isn’t a multi-generational trip. It’s two separate vacations sharing a lobby.
The question that saves you: what can the least mobile and the youngest person in the group both enjoy? Start there. A beach town. A lake house. A city with good public transit and benches scattered freely. A national park with accessible trails AND real hikes nearby. Aim for a place with range, so each generation finds its thing and nobody gets left out.
Tip: Let each household name one non-negotiable before you book. Grandma’s is the garden. The teens’ is a day with zero scheduled anything. Your younger kid’s is a pool. Yours is all about coffeeshops. When you know the non-negotiables up front, you plan around them instead of crashing into them mid-trip.
Talk money before you go (all of it!)
Cost is where good family trips can easily get derailed, so get ahead of that train. Decide who’s paying for what before anyone starts researching, not on the last morning while everyone’s doing math over lukewarm coffee, and disagreements easily arise. Aim for the lowest budget. That way, no one gets left out, feels weird, or overextends themselves. The whole point is to spend time together, not spend money together.
Some useful approaches: split the big shared costs (the house, the rental van, the group dinners) by household, and let each family cover its own extras. Or one person coordinates and everyone reimburses their share. Whichever you pick, say it out loud early so nobody’s guessing or quietly stewing or worrying. Money resentment is the one thing that can undo an otherwise gorgeous week – and unravel strong family bonds.
Choose a home base that accommodates everyone
Where you stay influences the entire trip. For multi-generational travel, a shared house almost always beats a scattering of hotel rooms. One kitchen, one big table, one gathering space, opportunities to share experiences around every corner, and everybody on their own clock instead of texting between three rooms to find each other and trying to meet at the breakfast buffet.
The kitchen is especially important. When you’re traveling with grandparents and little kids (and a tired parent), each day runs on food and rest. The kitchen lets each generation eat when it needs to. It also lessens the load on one person to make sure everyone is fed. I’ve written a full guide to choosing group vacation rentals for multi-generational travel.
Tip: look for a ground-floor bedroom, plenty of bathrooms, and a quiet room to escape to on top of the big common space. (For the whole framework, our pillar on family vacation rentals that actually work for kids pairs right up with it.)
Pace it for the toddler and the grandparent, not the marathoners
The fastest way to melt down a multi-generational trip is to pack the days like you’re twenty-five and traveling solo. You are not! Plan half of what you think you can do. Then cut a little more. The family members that want to go explore by themselves, will! That freedom of movement, quiet, space, and time is also a gift to themselves.
A restorative quiet walk, alone
Little kids and older or disabled people run out of energy at roughly the same point in the afternoon (there’s a beautiful symmetry to it, honestly). Build in downtime on purpose. A slow morning. A real rest after lunch. Art in the park. Time to read picture books together. A lunchtime concert in the town square. A restful outing to a park for play/birdwatching/chatting. An evening with nowhere to be.
The problems that arise on family trips are almost never about the thing everyone’s stressed about. The problems stem from being tired, overstimulated, and out of gas. Rest is the solution; schedule it in advance. Future you will thank today you.
Art in the park? Count us in
Let the group split up (this is the secret!)
Here’s my counterintuitive suggestion, and it’s the tip that makes everything else work: the best multi-generational trips are spent mostly together, with smart breakouts. Not all-together-all-the-time (that way lies exhaustion, and squabbling, and someone crying in a shop). Create varied groupings for outings and together time.
The teens and the parents might head up the trail while the grandparents and the toddler feed ducks by the water. Let Grandma take one grandchild to the museum, just the two of them, for meandering, sketching, and picking a postcard at the museum gift shop (a memory that kid keeps for LIFE).
The tired ones get a nap and the restless ones an adventure, the artists get inspiration, and we all reconvene at dinner with stories to trade. A trip where everyone does everything together is a trip where everyone is a little bit compromised all the time, and exhaustion is the result. Break into groups, and each generation actually gets its own trip!
A moment of contemplation - perhaps her favorite of the trip
Book the hands-on stuff that bridges the ages
Some activities can be interesting to every generation at once, and those are GOLD. A cooking class where the eight-year-old and the grandfather both get flour everywhere (and a fresh pasta recipe that will go into the family cookbook). A boat trip. A farm. A market where everyone hunts for something for a collaborative dinner. A supportive team that cheers on a teen's first surf lesson (and has the photos to commemorate such a longed-for event!). A bookstore where you can buy local picture books, and read them with your kids and grandkids (both a souvenir and literary travel at the source!).
Look for the gentle shared, hands-on, doing-something-together experiences. That’s where the bonding happens, across the age gaps, all at once.
Meals are the same. Cooking a few dinners together in the rental turns a trip into a reunion. Assign nights or tasks, let the kids help, and put everyone at one table. Need a starting lineup that feeds a crowd and pleases a range of eaters? Our easy family reunion meal ideas are built for exactly this.
The longed-for experience, FINALLY happening
All-adult multigenerational travel…it’s not always with kids
Multigenerational travel can include only adults! I often travel with my mom and adult daughter. Since we have traveled together for years (and my lifetime, with my mom!), we know each other’s rhythms, likes and dislikes, rising and sleep times, and what everyone loves. This adds an extra richness to adult multigenerational travel – not only the familiarity, but the joy of being with friends that are family.
When you’re grown enough to look out for others (discovering the yarn shop that gramma will absolutely love, asking a market vendor for the best boba recommendations in town for your beloved grandchild), the essence of the trip is both familiar and caring. Another bonus is sharing the themes of our family passions.
In Stratford, Ontario, we always see a musical (one year, it was Little Shop of Horrors!), and the next day, Shakes (Merry Wives of Windsor), along with the incredible Martin Guerre, at Meighen Forum at Stratford Festival. We’ve back-ended Taming of the Shrew with The Sound of Music. There are so many performances to choose from, but when we three peruse the list each year, we all tend to pick the same must-sees! We also love trying new restaurants (as well as old favorites), and LOVED taking a cooking class one year!
Intergenerational travel at its best: after our cooking class with Chef Eli Silverthorne at Stratford Chefs School
Build in time and space for rest, personal favorite places (see you at Bradshaw’s at 1pm!), and plenty of laughter. The ease of this particular multigenerational trip is just marvelous.
Look! It’s almost like Stratford planned it for our family: a record store right next to a yarn shop. Win/win! The photographer (myself) grabbed a coffee and basked in the sun. win/win/win!
Plan around mobility and health, vocally and early
Accessibility isn’t a footnote on a multi-generational trip (or on any trip, really). It’s part of the master plan from day one. Ask, kindly and directly, about knees and stairs and stamina and abilities and any medical needs, and build the trip so nobody has to be left out or feel like a burden. Don’t assume that because you’re related and familiar, you know what everyone’s accessibility needs are.
Practical to-dos: book ground-floor or elevator accommodation, confirm accessible bathrooms, keep a little medical kit and everyone’s essential info in one bag, rent a wheelchair scooter or hire a driver, and check that your big outings have seating and shade and short-walk options. For trips abroad, where the logistics get trickier, our tips for multigenerational international travel go deeper on passports, insurance, and crossing borders as a big group.
Make it a tradition
The best thing about a multi-generational trip is that we want it to happen again. Kids who grow up traveling with their grandparents carry those trips their whole lives, and the trips themselves get easier and richer each time, because you learn how your particular family travels.
Tip: while your family might be used to traveling one way for years, leave room (and continue to ask!) while planning for growth, changing interests and ages, different abilities or needs, or a swing in finances.
At the end of the trip, while everyone’s tired-happy and a little sad to pack to go home, ask the question that gives hope: where next? Start thinking about the next journey together before this one is even over. That’s how a single trip becomes the thing your family does, the through-line your own grandkids will talk about someday.
The journey together raises them, and us, in the best way.
Frequently asked questions
What is multi-generational travel?
Multi-generational travel means three or more generations traveling together, typically grandparents, parents, and kids, on one shared trip. It’s an increasingly popular kind of family travel, and the appeal is simple: real, unhurried time together that everyday life rarely allows.
How do you plan a multi-generational trip everyone enjoys?
Choose a destination the youngest and least-mobile members can both enjoy, agree on the budget and cost-splitting before you book, pick a shared home base with a kitchen and an accessible bedroom, pace the days with real downtime, and let the family break into smaller groups so each generation gets its own trip within the trip.
How do you handle different ages and energy levels on a family trip?
Plan breakout time, not just together time. Send the high-energy crowd off on the big adventure while the youngest and oldest do something slower, and reconvene at meals. Build downtime into every day, and pace the itinerary for the toddler and the grandparent rather than the marathoners.
What are the best destinations for multi-generational travel?
Places with range: a beach or lake town where you can do a lot or a little, a city with good transit and plenty of seating, or a national park with both accessible paths and real hikes. The best destination is the one where every generation finds its thing and nobody’s stuck waiting around for something to happen.
The trips where the whole family travels together are the ones your kids will still be talking about decades from now. Plan them for every age, leave room to split up and come back together, and let the road do what it does best.
Family love
Where’s your family headed, and who’s coming along?
Further family travel resources here on Wandering Educators
First, to make you laugh
- Why You Should Vacation with your Family
- How To Survive Vacationing With Your Family
- Eleven Types of Family Vacation Photos
Multi-generational Travel Tips
5 Important Tips for Multigenerational International Travel
6 Easy Family Reunion Meal Ideas
Lonely Planet's Family Travel Tips: Top 5 Destinations for Multigenerational Travel
Accommodations Tips
Group Vacation Rentals for Multi-Generational Travel: How to Choose One That Actually Works
Family Vacation Rentals: How to Choose One That Actually Works for Kids
Budget Travel Tips
Budget Travel: 5 Ways to Save Money & Live Like a Local
Road Trip 101: Top 10 Ways to Save Money on the Road
Road Trip 101: Ten Tips to Save Money on Accommodations
Top Tips for Budget Family Travel
Traveling on an Extremely Tight Budget with a Group
Travel Budgeting: Don’t Cry, Make A Plan
Expert Shares Top Tips for Budget Travel
Lifelong Learning Starts Young (and never ends!)
Places to Travel with Family: Nine Trips That Teach Your Kids Something Real
Educational Family Trips: How to Raise Kids Who Love to Learn While Traveling
7 Tips for teaching your kids to appreciate art museums
Cultural Travel: A Guide to Trips That Teach
Why We Love Traveling with our Daughter
Family Travel Expert interviews, with the best insight
Family on the Loose: The Art of Traveling With Kids
First, Read This: Lonely Planet's Family Travel Handbook
An Expert Shares How to Create Happy Family Travel
Excellent Family Travel Resource: The Travel Mamas’ Guide
Jessie Voigts is the founder and publisher of Wandering Educators. She has a PhD in International Education, has lived and worked in Japan and London, and traveled around the world. She is constantly looking for ways to increase intercultural understanding, and is passionate about study abroad and international education. She LOVES family travel (can you tell?)!
Find her online via Instagram, Facebook, or LinkedIn.