There are vacations you take to relax, escapes to explore somewhere new and getaways you take simply because the entire family needs a change of scenery. And then there are the trips that become part of your family’s story—the ones your grandchildren will still be talking about long after they’ve outgrown their favorite stuffed animals and started rolling their eyes at your jokes.
Traveling with grandchildren offers something particularly special: the chance to see the world through younger eyes while sharing a little of your own wisdom along the way. Whether it’s spotting an elephant on safari, learning to make pasta from scratch or watching their faces light up at Cinderella Castle, these are the moments that stick around longer than any souvenir.
Of course, planning a multigenerational getaway isn’t quite as simple as booking a flight and hoping everyone gets along. Between different interests, energy levels, bedtimes and opinions about what’s for dinner, keeping everyone happy can feel like an Olympic event. But the payoff? More than worth it.
Just ask Theresa Bauman, a travel advisor and author of Theresa B Travels, who still remembers visiting Korea with her grandfather when she was 12. Her family explored his hometown, visited his childhood home and met relatives she hadn’t known existed. Decades later, it remains one of her most treasured childhood memories.
And that’s the beauty of traveling together. You aren’t just showing your grandchildren the world. You’re giving them stories and memories they’ll carry into adulthood.
With that in mind, we asked travel advisors and family travel experts which trips grandparents should take with their grandchildren at least once. From the rolling hills of the English countryside to the magic of Walt Disney World, we narrowed their recommendations down to six adventures worth putting on the family calendar.
Related: Planning a Multigen Trip? Travel Experts Say These Are the 5 Best Destinations for Every Age
7 Best Trips to Take With Your Grandchildren
1. Escape to a Country House in the Cotswolds, England
Lucknam Park, Emblems Collection
If your idea of the perfect family vacation involves charming villages, sprawling gardens, cozy country houses and afternoons that stretch deliciously into evenings, the Cotswolds might just be your happy place. Think The Holiday meets a multigenerational family reunion, only with better scones and significantly more picturesque scenery.
Amy Norman, Founder and CEO of luxury travel company Nellie, considers the Cotswolds one of her favorite destinations for grandparents traveling with grandchildren.
“I grew up in the UK, so I’m partial to the Cotswolds, especially for families who want countryside, local traditions, and plenty of time together. I’d look for a big, beautiful villa or country house with shared living spaces and enough bedrooms for privacy,” she shares.
One property that fits the bill is Lucknam Park, a sprawling 500-acre country estate on the southern edge of the Cotswolds, within easy reach of postcard-perfect villages like Castle Combe and Bradford-on-Avon, but blissfully removed from the tourist crowds. Its spacious cottages are particularly well suited to multigenerational stays, with private gardens and terraces, fully equipped kitchens, wood-burning stoves and cozy living rooms made for family game nights. In other words, plenty of room for everyone to be together without being together every waking moment.
“As for what to do, we lean toward intimate, hands-on activities like baking scones in a local home, foraging followed by lunch on a family farm, and tea with the owners of a historic estate, as well as a guided countryside walk and meeting local craftspeople keeping traditional skills alive,” says Norman.
When to go: Norman recommends May or September, although summer works well for families coordinating around school vacations. Book your country house well in advance, particularly for larger groups.
2. Go on an African Safari in Kenya
Angama Mara
There are few experiences quite like watching a child’s face when they spot their first elephant roaming across the African savanna. Unless, of course, it’s watching Grandpa’s face when he spots his first elephant, too.
“There’s nothing like experiencing and seeing the wonder of an African safari through a child’s eyes, especially for grandparents who may not have had that kind of experience themselves yet,” says Elizabeth Gordon, Co-Founder and CEO of Extraordinary Journeys. “It’s a shared wildlife experience that every generation feels in the same moment, and it stays with you for the rest of your lives.”
Gordon particularly recommends Kenya for families with younger children, thanks to its incredible wildlife and opportunities to customize the experience around different ages and energy levels.
“Kenya works especially beautifully with little kids—you can start in Nairobi with the baby elephants at the Sheldrick Wildlife Trust orphanage, then head to a private conservancy, where families have more flexibility than in the national parks and reserves, with options like guided walks and bush breakfasts. Having your own vehicle and guide means you can stop for snacks and naps, and that slower pace is exactly what makes it magical for all ages.”
Norman also recommends Kenya’s Maasai Mara, particularly Angama Mara, where interconnected tented suites make it easier for families to stay close while enjoying their own space. Private game drives can be tailored to everyone’s interests, and hot-air balloon excursions offer an unforgettable perspective on the landscape for those old enough to participate.
For Gordon, the appeal is personal, too. “My mother is taking her grandchildren to Kenya this year for her 80th birthday, and everyone has been excited for months, from the minute we started planning it.”
Now that’s a birthday present that beats another sweater.
When to go: Kenya offers safari opportunities year-round, but Norman recommends July through September for families hoping to witness the Great Migration in the Maasai Mara. Wildlife sightings and river crossings are never guaranteed, so go for the entire safari experience rather than one particular moment.
Good to know: Families with very young children might also consider South Africa’s malaria-free Madikwe Game Reserve. Gordon recommends Madikwe Safari Lodge, which offers shorter, slower game drives designed with little explorers in mind.
3. Discover Your Family Roots in Italy
Experience BellaVita
Some family vacations are about discovering somewhere new. Others are about discovering where you came from.
For grandparents hoping to pass down a little family history, an ancestry trip can be one of the most meaningful experiences to share with grandchildren—particularly when it involves exploring the villages, traditions and places that shaped earlier generations.
Marino Cardelli, Founder of Experience BellaVita, specializes in tailor-made cultural, culinary and ancestry trips in southern Italy, often working with American families tracing their Italian roots. He’s witnessed grandparents returning to villages their own grandparents left more than a century ago, visiting family homes, stepping inside churches where relatives were baptized and even meeting distant cousins they never knew existed.
Cardelli particularly recommends Abruzzo, a region east of Rome where medieval villages, the Gran Sasso mountains, national parks and the Adriatic coastline offer plenty to explore beyond ancestral hometowns. One day might involve tracing family history through a village, while the next could include truffle hunting with dogs, learning to make pasta with a local family, canoeing or spending an afternoon at the beach.
His biggest piece of advice? Don’t turn the entire vacation into a history lesson.
“I always tell grandparents not to plan the whole trip around what is meaningful only to them. Get the grandchildren involved and let them choose some of the activities too. It makes a huge difference.”
In other words, yes to exploring Great-Grandpa’s hometown, but perhaps follow it up with gelato and a boat ride.
When to go: Cardelli recommends May, June, September and early October for comfortable weather and fewer crowds. He suggests avoiding July and August when possible, particularly around Italy’s busy mid-August holiday period.
Where to stay: Consider a villa, small bed-and-breakfast or agriturismo, where everyone can enjoy a more authentic experience without sacrificing their own space.
4. Unplug on a Rogue River Rafting Trip in Oregon
OARS
Convincing grandchildren to put down their phones for five minutes can sometimes feel like an extreme sport. But take them rafting through Oregon’s wilderness for several days, and suddenly there are far more interesting things to focus on than whatever’s happening on TikTok.
Cari Morgan, who has spent 15 years working in the rafting industry and represents adventure outfitter OARS, says multigenerational river trips are becoming increasingly popular among baby boomers eager to share outdoor adventures with their families.
Two summers ago, Morgan’s 72-year-old father-in-law joined her husband and sons on a five-day rafting trip down Oregon’s Rogue River. Since Grandpa John lives on the opposite side of the country, it was an opportunity for everyone to spend meaningful time together without the usual distractions.
“We weren’t the only multi-generational family on the trip,” Morgan recalls. “Another group included a grandmother traveling with her daughter and two grandsons. There was also a grandmother who had rafted the Grand Canyon in the 1970s and wanted to introduce her three grandsons to the magic of a river trip.”
Talk about passing down a sense of adventure.
“Days are filled with rapids, side-canyon hikes, and wildlife, while evenings center around playing games, sharing meals, and swapping stories. With no screens or everyday distractions, and guides taking care of all the logistics, families get the kind of undivided time together that’s almost impossible to get on any other vacation.”
And because experienced guides handle the logistics, families can focus on enjoying the experience rather than figuring out who’s in charge of dinner or where they’re sleeping that night.
When to go: Summer is a popular time for family rafting adventures, although the best departure depends on the river, water conditions and ages of the children.
Good to know: Not every rafting itinerary is appropriate for every age or ability level. Check minimum-age requirements, swimming considerations and the physical demands of the trip before booking. Some families may prefer a gentler river experience over more challenging whitewater.
5. Sail Through the Greek Islands on a Private Yacht
Getty Images
Ancient mythology, sun-drenched islands, impossibly blue water and enough Greek food to keep everyone happy? Sign us up.
For families who love a little history with their beach vacation, Emmanuel Burgio, Founder and CEO of Blue Parallel, recommends pairing a visit to Athens with a private yacht adventure through the Greek Islands.
“Athens and a private yacht journey through the Greek Islands is hard to beat for grandparents and grandchildren because it has the ancient history and Odyssian mythological draw with so many fascinating sites to explore, plus of course the stunning Mediterranean playground—and lots of time to relax and unwind between islands, which is important for older travelers who can’t always be “on” in the same way as younger generations,” says Burgio.
He recently organized a Greek island adventure for 12 family members ranging from a one-year-old to grandparents in their 70s. The group explored Athens and the Acropolis before sailing through the Cyclades, discovering destinations such as Santorini, Delos and Paros.
“We recently planned a Greek island adventure for 12 family members ranging from a one-year-old to grandparents in their 70s, and with a dedicated crew and flexible itinerary, everyone could participate according to interests and energy levels while still sharing the experience.”
That means the adventurous teenagers can head out for a hike, the younger children can splash around in the water and the grandparents can enjoy a leisurely afternoon on deck without feeling like they’re missing the trip. And everyone can reconvene for dinner with a view.
“The bonding that happens when sharing this kind of history and adventure and stunning scenery is the kind of unforgettable experience that will stick with a family forever.”
When to go: Late spring and early fall can offer pleasant weather and fewer crowds than peak summer. Families tied to school calendars can also enjoy the islands in summer, although popular destinations tend to be busier.
Good to know: A private yacht is a significant splurge, but the flexibility can be especially valuable for larger families traveling with children and grandparents of different ages.
Related: These Are the 7 Best Greek Islands to Visit, According to Samantha Brown
6. Make Magical Memories at Walt Disney World, Florida
Photo by Matt Stroshane, courtesy of Disney
Sure, you could take your grandchildren anywhere in the world. But there’s something about watching their faces light up at the sight of Cinderella Castle that never gets old.
Amanda Reed, a travel advisor with White Gloves Travel Co. at Reeds Do Travel, has helped plan more than 70 multigenerational Disney vacations, including trips to the theme parks and sailings with Disney Cruise Line.
“While there are dozens of destinations across the globe that would make for memorable family vacations, Disney evokes memories, sentimentality, and nostalgia in a way that other trips might not be able to (unless that other destination is one with significant family memories from past trips).”
Reed remembers seeing Aladdin in theaters as a preschooler, celebrating Disney-themed birthdays and taking vacations her mother carefully planned. Today, her mother gets to experience Walt Disney World through her grandchildren’s eyes.
“Especially for my generation—’80s and ’90s babies now raising kids of our own—taking a Disney vacation with our parents and our children together is such a special way to both revisit old memories and create new ones.”
For families who want the Disney magic with less walking, Reed also recommends Disney Cruise Line. With meals included, entertainment for different ages and the ability to return to your stateroom for a midday break, cruising can be a gentler introduction to multigenerational travel.
When to go: Bauman recommends avoiding major holidays and school breaks when possible. If taking the grandchildren out of school isn’t an option, early or late summer may be worth considering, although crowds and Florida’s heat remain factors.
Budget: Bauman suggests planning for approximately $1,500 to $4,000 per person, depending on the length of the trip, accommodations and activities.
Insider tip: Consider Lightning Lane options and advance dining reservations to make the most of your time without spending the entire vacation waiting in lines.
And remember, while the rides and fireworks are wonderful, the real magic is getting to experience them together. Because years from now, your grandchildren probably won’t remember exactly how many attractions you managed to squeeze into one day. But they’ll remember who was standing beside them when the fireworks began.
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