“It was awesome,” said my four year old when I asked her recently if she remembered the cooking class we took six months ago with her five-year-old cousin and grandparents at Mayakoba in Mexico. “I cut stuff and mashed stuff and squeezed stuff and made guacamole!” she continued. During the multi-generational culinary lesson, the young ones sipped homemade lemonade, while us adults drank delicious maracuya mezcalitas. Our wonderfully patient yet perfectly energetic El Pueblo Cooking School instructor, chef Sandra de la Mora, enlisted my daughter Indah to don rubber gloves and help skewer al pastor–seasoned pork and pineapple while de la Mora explained the dish’s conception.
Every family member had an important job, but what I remember most vividly—besides happily devouring the delicious guac, tacos, steak, and cheese quesadillas (for the kids), as newly accomplished chefs—is my dad manning sizzling skillets while his two eldest grandchildren stood sweetly on stools beside him, rapt. The little ones lasted an impressive hour before their attention waned (at which time there were beanbag chairs and toys at the ready).
The experience, one of those where my face hurt from smiling by the end, formed a core memory for me. For my parents, too. After all, it checked a lot of boxes for best-case-scenario on a trip whose members had a staggering eight-decade age span. Rest assured, with us sprawled across three continents, it took months of discussion and debate, research and planning to get there. Before my sister and I had kids, designing vacations with our parents was complicated enough. There was always one person advocating for a hot beach holiday, another seeking art museums, and someone wanting adventures that involved hiking or boats. Add three grandkids to the mix and the equation has become infinitely more convoluted.
Anyone in the stress-inducing sandwich-generation position of trying to please both their parents and children knows it can at times feel impossible. But don’t despair. Here are some top tips from someone who is often put in the position of spearheading travel plans. They should lead to loads of fun without you going crazy in the process.
Enlist a travel advisor and/or tour operator if the trip is complex
Start out by asking: What’s the goal of this trip? Is it blissful relaxation at a tropical beach resort, or are you aiming more for an adrenaline-fueled adventure in nature? Depending on where you land, especially if it’s in a far-flung destination such as South Africa, Iceland, or New Zealand, enlist a travel advisor or a professional coordinator such as Extraordinary Journeys that specializes in weaving several generations’ interests into highly customized itineraries.
Make sure the trip you’re planning meets everyone’s needs
Does an older family member require medical services nearby to feel safe? Is someone neurodivergent or have accessibility needs? Is there an infant on board? On a big family trip, one person’s discomfort can affect everyone in the group. List what you all collectively need and find a destination that aligns.
All-inclusives are evolving and encompass a wide range of multi-gen-friendly properties like the Mohonk Mountain House in New Paltz, New York.
Photo by Ken Hayden/Courtesy of Mohonk Mountain House
Consider an all-inclusive
If you’d asked single, childless me if I’d recommend all-inclusive resorts, my answer would have been a resounding no. But as much as we may not want to admit it, kids change things (and all-inclusives are changing, too). Your parents getting older and becoming grandparents changes the travel equation, too. In my experience, staying at all-inclusive properties is the easiest way to make everyone happy and find peace while also guaranteeing zero stress over who’s paying for what. If a kids club is available, you can certainly send the little ones there when there’s a desire for adults-only time (and it’s also a good venue for grandparents to play with them—with extra sets of hands to take the pressure off). Grand Velas’s Mexico resorts and Mohonk Mountain House, a Victorian castle in the Hudson Valley, illustrate the range of what’s possible in the increasingly attractive category.
Think about transportation logistics in advance
With such a big group, getting around in cars (plural) can be a real pain—take it from a gal who thought it would be no biggie to Uber around Vancouver with my toddler, baby, husband, and in-laws but who discovered that, actually, it’s no fun ordering two separate SUVs and trudging into a museum with a pair of car seats to store. Think about logistics ahead of time. For certain families, cities can make a lot of sense because trains, sidewalks, and maybe even e-bikes make it easy to explore. But a resort can be appealing to families who prefer to have most services within easy reach.
Book hands-on activities that create bonding opportunities
Especially if multi-gen trips are not a regular occurrence, use yours as a chance for members of the family to do something they’ve never done before. This could mean arranging a private cooking class like the one we took at Mayakoba. At Rosewood Castiglion del Bosco’s La Canonica Cooking School in Tuscany, several generations can join forces to create their own pasta or pizza, while biscuit-making and crabbing are possibilities at South Carolina’s the Charleston Place. A family fishing outing in the crystalline waters around Sonora Resort in British Columbia’s Discovery Islands should excite everyone. In Houston, a Post Oak Hotel package offers to helicopter guests to the Johnson Space Center to meet a NASA astronaut who’ll take them behind the scenes, including mission control. And as my dad told me after his recent multi-gen trip with my sister’s family to Kenya’s Umani Springs Lodge—a Sheldrick Wildlife Trust elephant orphanage—“kids like elephants, older folks like elephants, everybody likes elephants.”
Consider activities like a cooking lesson that can bring together family members across different generations for a memorable hands-on learning experience.
Photo by Kathryn Romeyn
Create “breakout groups” for some activities
A family trip does not mean everyone needs to be together at all times. Far from it. Trade kids around, so that grandparents, aunts, uncles, nieces, nephews, cousins, or any combination of family members who don’t regularly get to see each other have the chance to bond in a more intimate setting. Perhaps grandma takes her grandson to an art workshop at Tides Inn’s Maker Space after bird-watching along a Virginia forest trail or an uncle goes sea kayaking with his niece at the Cove in Eleuthera, Bahamas.
Look to nature for experiences that thrill every generation
My dad, always the person trying to please everybody on trips, pointed out to me that “nature is calming and soothing and easy on everybody.” More nature, less artificial stimulation (i.e., TVs, smartphones, computers, tablets, Nintendos) is a dependable recipe for deepening connections. That might look like a beach holiday or it could be a place with incredible ecological diversity such as Costa Rica, where families can take nocturnal amphibian hikes at a property like Hacienda AltaGracia, Auberge Resorts Collection. Jackson, Wyoming, is also an amazing destination with year-round outdoor options, including sleigh rides, dogsledding, skiing, floating, hiking, fly fishing, and wildlife safaris. Fiji enables travelers of all ages to engage in a love of the ocean, with Jean-Michel Cousteau Resort taking special care with the youngest generation.
Ensure there’s enough downtime
Don’t run yourselves ragged by overscheduling every day. Allow time for naps and/or quiet time, both for the young and older (and everyone in between). Along those lines, don’t require everyone to participate in all activities—and never force anyone into something they don’t feel comfortable doing. The goal is sweet memories, not traumatic ones. It’s OK to sit things out.
Think about the future—and making a tradition
A multi-generational trip in its very nature is sure to rouse nostalgia, so consider leaning into it and perhaps starting a new family tradition by traveling to a place you’ll all return year after year. Is this a place where your kids might one day bring their kids? Somewhere that gets embedded in your family’s story? For me, my earliest and most indelible childhood memories are from the small Adirondack Mountains lake where my dad grew up spending every summer and his dad did, too, before him—making s’mores around a campfire, diving into fresh, goosebump-inducing water, eating sandwiches atop a mountain lookout, spotting shooting stars from the dock. It feels so natural that this year’s visit will be my four year old’s fifth at that same special place. Sea Island Cottages off Georgia’s coast, the Tryall Club in Jamaica, San Diego’s Hotel del Coronado, and Alisal Ranch in Santa Barbara’s wine country are time-tested multi-gen retreats where people who are now parents or grandparents may have first visited as kids.
This article originally appeared online in 2015; it was most recently updated on May 12, 2025, to include current information.
