Best Multigenerational Trips: Family-Friendly Vacation Ideas

Multigenerational trips are a rising travel trend, and that makes sense. A vacation between grandparents, kids, and grandkids gives extended families time together without the expectations of holiday gatherings, and with so many vacation schedules to juggle with quality time, families are finding it easier to simply see each other while they relax. To help make your own three-generation getaway work better, it helps to pick places with plenty of options for every age, because not everyone wants to do the same thing. It also helps to decide ahead of time who’ll pay for what. Whether riding horses across the open plains, exploring a city, rafting rivers, or cruising, these diverse ideas offer vacations that your family will remember for all the right reasons.

Dude Ranches

Whether you never-ever put a foot in a stirrup or you can lope like Annie Oakley, dude ranches make for memorable multi-family vacations, especially if they’re resort properties where choosing a trail is as easy as booking a massage, tennis workshop, or fly-fishing outing. Such extra options not only assuage the saddle-sore but also cater to non-riders. The best ranches feature lessons for all ages, rides for grade-schoolers and teens, as well as pony excursions for little ones. At resort ranches, lodging ranges from comfortable to luxurious rooms, cabins, and homes staffed by real chefs. In the evening, get together over s’mores, storytelling, roping, and square dancing. At some ranches, the all-inclusive fee covers horses, lessons, accommodations, and meals while other properties price à la carte. For the Ranch at Rock Creek (pictured), a Relais & Châteaux luxury property 20 miles southwest of Philipsburg, Montana, summer and fall are prime saddle time. The best horseback riding weather at Tanque Verde Ranch, Tucson, Arizona, is February through April.

All-inclusive Caribbean Resorts

All-inclusive resorts restrain budgets from ballooning—the pervasive risk of all multigenerational trips. It’s not a problem when the grandkids want more tennis, kayaking, or windsurfing, or when teens grab second helpings of lobster or steak. The upscale Grand Velas Riviera Maya, Mexico (pictured), a luxury resort on 206 acres, delivers good food and a sense of expansiveness. The oceanfront, family-friendly Ambassador Class rooms are around 1,100-square feet, and the spa, which administers treatments inspired by local traditions, provides ample space for relaxing. At the kids’ clubs, those aged 4 to 12 years take mariachi lessons, listen to stories, and enjoy arts and crafts, and teens get foosball, air hockey, and video games. At Beaches Turks & Caicos, Providenciales, set on 75 acres, expect more crowds but also more activities—wakeboarding, sailing, scuba diving—as well as no-extra-fee child care for infants through 3-year-olds, plus a full day’s worth of activities for kids 4 to 17. The waterpark’s geysers and slides divert kids for hours, and the Sesame Street characters thrill preschoolers, who can bake cookies with Cookie Monster, take a nature walk with Big Bird, or listen to stories with Elmo for added fees. For a bit of luxury, consider a two-bedroom suite or a 3- to 4-bedroom villa. Both come with butlers.

River Rafting

Rafting is exhilarating, and the teamwork required to maneuver tricky waters goes a long way toward building family bonds. Watching grandparents paddle through a Class III rapid elevates their status from fuddy-duddy to fabulous in the eyes of most grandchildren. Both the Rogue River, Oregon, and the main section of the Salmon River, Idaho, combine rapids with riffles—perfect small eddies for kayaking—and stretches of smooth water for floating. On ROW’s and OAR’s family trips, an additional staff member engages the kids with hikes and games. On ROW’s Rogue River lodge-to-lodge trips, families paddle each day but retire to comfortable cabins each night. If you have older teens, consider Snake River’s Hells Canyon, Idaho, known for big waves and big drops. For something milder, at the Nantahala Outdoor Center, near Bryson City, North Carolina, you can build a multi-day adventure by overnighting at NOC’s cabins or 8-bedroom motel. By day, take an excursion on the Great Smoky Mountains Railroad, zipline through the trees, hike on the Appalachian Trail, or explore the Nantahala River at NOC’s paddling school.

City Explorations

Like many big cities, Boston’s mix of history, art, outdoor sites, and science attractions enables families to follow their interests without roughing it. Along the Freedom Trail, grade schoolers find the Old North Church and other places they’re learning about. Turn rebel by dumping tea in the harbor at the Boston Tea Party Ships & Museum. Little ones like to build houses and blow giant bubbles at the Boston Children’s Museum as well as climb the duck sculptures in Boston Public Garden (pictured). At the New England Aquarium, animal lovers can see harbor seals, penguins, and endless tanks of fish. At the Museum of Fine Arts, admire one of the largest collections of Monet paintings in the United States. Science-oriented teens find fossils and dinosaurs to ogle at the Museum of Science (one of the best in the country) and kinetic sculptures to activate at the MIT Museum, across the river in Cambridge. In season, enjoy family bike rides along the Charles River Esplanade, Boston Red Sox baseball at Fenway Park, or ice skating on the frozen Frog Pond in Boston Common. Boston is just one example, though; many of America’s historic cities are equally good playgrounds for multi-age family vacations.

Cruises

Megaships are now being designed expressly for families. The slate of amusements is huge and surprising: zip lines, bumper cars, laser tag, movies, skydiving simulators, as well as multiple pools and children’s activities—older, well-behaved grade-schoolers and teens enjoy the freedom to roam the ship without you. When the ship stops at new ports, diverse itineraries give you even more options. Europe’s castles intrigue grade-school princesses and knights. The Continent’s city art museums and trendy boutiques draw tweens and teens. In Hawaii, go local with surfing or kiteboarding lessons. The Caribbean draws beach lovers, snorkelers, sailors, and shoppers. Easy to pay for, cruise fees already include lodging, entertainment, standard meals, plus children’s and teen activities—with no unexpected outlays to break your budget. Just practice tough love and limit the add-ons, and be sure the line you choose has programming suited to the children in your group. Royal Caribbean, Carnival, Princess, Norwegian, and Disney lead the way in the industry for mounting comprehensive kids and teens’ diversions and making sure every age level—including yours—is amused and comfortable. Carnival’s children’s camp operates for tots as young as 2, whereas the cutoff for other lines’ youngest participants is age 3.

Villas, Houses, Condos

Villas, houses, and condos provide extended families with more space for the money than multiple hotel rooms, plus the home-like conveniences of living areas and kitchens. Your time will also be your own, with no pressure to join scheduled activities. Many rental companies have search engines that allow you to specify if you want a property at a beach, in the mountains, or in the city. The key: understanding the rental. A luxury villa that comes with a cook and maid eliminates hassles but cuts out family cooking time. A swimming pool makes it easy to splash with the grandkids. WIMCO’s Caribbean villas (one in Anguilla is pictured) come with housekeeping and its Jamaica, Mustique, and Barbados properties include a cook. Resorts that rent their own condo units carefully maintain them and typically include maid service. For homes and condos listed by owners on rental sites, be sure to read user reviews as well as the fine print to assess the property and know what’s included. HometoGo compares prices on some 300 vacation rental websites, including VRBO, HomeAway, and Booking.com.

Costa Rica

Costa Rica, a relatively easy country to navigate, is a compact land of volcanoes, beaches, and rainforests that shelter scarlet macaws, toucans, and sloths. From San José, Costa Rica’s capital, drive past coffee fields and slopes of mango trees to Poas Volcano, whose crater bubbles with sulfurous waters. Crocodiles and scarlet macaws are the stars of Carara National Park. If your family prefers a resort, consider the Four Seasons Peninsula Papagayo (pictured), Guanacaste, overlooking the Pacific Ocean. Kayak from the beach, go on a snorkeling outing, and day trip to Rincón de la Vieja National Park, where howler monkeys scamper through the rainforest and trails amble past fumaroles belching steam. In addition to hotel rooms, the resort’s three-bedroom homes and a villa sleeping 14 are good options for extended families. While the youngsters 4 to 12 enjoy crafts and water play at the kids’ program and teens swim at the beach, parents and grandparents kick back with coconut latte scrubs and massages in the spa.

National Parks and Nearby Towns

Combine the wonders of Yellowstone National Park with the western culture of Cody, Wyoming, the park’s eastern gateway. Even the most blasé kids look up from their phones as the Old Faithful geyser shoots spray 100-plus feet into the air or a herd of bison moseys in front of the car. Learn about the park on an outing or multi-day trip by Yellowstone Forever, the park’s nonprofit partner. Naturalists tell you about the wildlife and set up high-powered telescopes so you can spot wolves in the hills and goats on mountain ridges. To eliminate the hassles of planning, driving, and, possibly arguing over what to do next, consider the five-night “Yellowstone for Families: Mammoth to Old Faithful” itinerary, which targets those with children ages 8 to 12. After Yellowstone, visit Cody. President Teddy Roosevelt called the drive from Yellowstone’s east entrance to Cody “the most scenic 50 miles in the world.” At the Buffalo Bill Center of the West, five museums showcase firearms, Plains Indian culture, Western art, and wildlife, including grizzly bear claws and live encounters with hawks and owls. In summer, watch cowboys ride bulls and race horses around barrels at the Cody Nite Rodeo. Many of the biggest national parks in the American West have similarly wide ranges of options.

Bicycling Trips

There’s something freeing (as well as nostalgic) about the wind-in-your-face sensation of bicycling. The maritime-feeling, 22-mile Cape Cod Rail Trail in Brewster, Massachusetts, goes through six Cape Cod towns. For mountain scenery, tackle the 34-mile Virginia Creeper Trail (pictured) that begins in Abingdon, Virginia, and ends in Damascus, Virginia. Affording spectacular views, the trail crosses 47 wooden trestle bridges, including Creek Junction, known for its trout fishing. On guided family trips, mileage is kid-paced and outfitters will tote weary toddlers as well as trailer cycles, a one-wheeled bike that hooks to yours, that youngsters like to ride in. Backroads’ “San Juan Islands Family Multi-Adventure Tour,” aimed at teens, adds sea kayaking and hiking. Butterfield & Robinson also arranges a variety of biking and multisport trips for families at destinations around the world.

Resort Stays

Sometimes it’s more relaxing to base the extended family at a destination resort that lists a wealth of activities—sort of like a cruise without an ocean. Among the many programs at The Broadmoor, an upscale, 3,000-acre resort in Colorado Springs known by some as the “grande dame of the Rockies:” golf, tennis, fly fishing, horseback riding, hiking, mountain biking, rock climbing, ziplining, falconry, pickleball, and a spa. Paddle a canoe or captain a boat in a family armada across the lake. At the seasonal Bee Bunch kids’ group, ages 3 to 12 visit the Cheyenne Mountain Zoo, take pony rides and go on nature walks. Seven Falls (pictured), rated among Colorado’s most scenic waterfalls, is a mile from the resort. For more Colorado vistas, drive the switchbacks to the 14,115-foot summit of Pikes Peak and explore Garden of the Gods, where sandstone formations eroded by the rain and wind dominate the landscape. The Broadmoor has standard hotel rooms, but it also rents connecting suites and cottages with up to eight bedrooms. Now everyone’s happy and has his or her own space. Problem solved!