It’s true: Traveling becomes more complex as the number of people on the trip grows. And trip planning becomes increasingly complicated as the age span among participants stretches. Yet these are two hallmarks of nearly every multi-generational holiday.
But while it’s not always easy to plan a big multi-generational trip, the payoff is more often than not well worth it. Lifelong, core memories are essentially guaranteed. And one of the surest ways to find happiness for all is to select a destination and accommodations with plenty of options and activities baked in. From a western dude ranch to an African safari or immersive cultural experience in Japan, some destinations simply spark wonder—and from that usually follows collective joy.
The idea of pulling off an epic multi-generational trip can be daunting, but here we’ve collected eight places to go with your immediate, extended, chosen, and/or blended family to create bonding moments that will stay with everyone well into the future.
The U.S. West
At Alisal Ranch, generations of families can gather for horseback riding and roasting s’mores among the oak-filled landscapes of California’s Santa Ynez Valley.
Courtesy of Alisal Ranch
You don’t have to watch the hit TV series Yellowstone to know that there’s lots of excitement on a ranch. Dude ranches continue to be a popular family holiday destination because they offer something for everyone. The beautiful natural landscapes appeal to adults who spend too much of their lives indoors and wide-open spaces are perfect for active youths. Fresh, clean air along with horses and farm animals, and activities that often include riding, hiking, fishing, swimming, and hayrides, with guest ranches typically following a choose-your-own-adventure type of format—it’s a recipe for vacation victory.
Where to stay
The Ranch at Rock Creek, Montana
Sprawling across 6,600 acres of a valley in western Montana with more than 20 miles of on-site hiking trails, this all-inclusive 19th-century homestead is a no-brainer for large family groups. The Moose House log cabin sleeps up to 11, while the Red Tail and Golden Eagle houses are beside each other and accommodate up to 10 people each, allowing plenty of space for multi-gen travelers from 1 to 90 years old. Folks can be as active as they wish, on horseback or snowmobile, but the frontier skills, sapphire mining, and naturalist classes are appealing activities for all ages. Flint’s Forest Rangers is the super-experiential kids program for 4–12 year olds when the adults want to do their own things.
Alisal Ranch, California
Situated within Santa Barbara’s wine country and with 10,500 acres of horseback heritage, Alisal is a Wild West retreat that’s long attracted multiple generations year after year. Picture horseback riding, getting soft serve ice cream at all hours at the Waggin’ Tongue, creating in the craft room, riding a hay wagon to a destination breakfast, and coming together all dressed up for “cowboy formal” dinners to share the day’s stories. The stylish Jackson, Turner, and Sycamore houses each have three en suite bedrooms plus a central living room for families who want to be close but still have their own space. And a selection of cottages sleep between three and five.
British Columbia, Canada
Take the extended family completely off the grid to connect in nature at Clayoquot Wilderness Lodge.
Photo by Jeremy Koreski/Courtesy of Clayoquot Wilderness Lodge
No matter the season, British Columbia speaks to families who love to be active at every age. Even cities such as Vancouver and Victoria feel more outdoorsy than most, with scenic suspension bridge walks and whale-watching boat trips. In the mountains there’s world-class downhill skiing and snowboarding and and cross-country skiing in the winter, or mountain biking, hiking, and tubing in warmer months. Continue north and you’ll find Tofino for surfing, hot springs hikes, and cultural canoe trips, Desolation Sound for grizzly bear viewing, and glamping-style eco-resorts hidden in wilderness.
Where to stay
Clayoquot Wilderness Lodge
Situated on traditional Ahousaht First Nations territory in the Clayoquot Sound, west of Vancouver, this seasonal lodge (open from May to September) is as off the beaten path as it gets, amid pristine wilderness and hugging a Pacific coastline where whales and otters play. Wildlife viewing is just one element of the customizable all-inclusive itineraries that can also incorporate canyoneering, glacial immersions, heli experiences, archery, and equestrian adventures. Among the 25 Canadian safari tents is a two-bedroom Hillside Family Tent with a private deck and outdoor cedar shower. Clayoquot Wilderness Lodge has a minimum age of six.
Four Seasons Resort Whistler
Think of this Whistler resort as your headquarters for dreamy fun on the slopes all winter, and other mountain-centric capers—whitewater rafting, ziplining, salmon bakes, and glacier seaplane tours—when it’s warmer out. The residences, which run up to four bedrooms spread over 3,700 square feet with outdoor balconies, a full gourmet kitchen, living and dining room plus private laundry room, make fantastic multi-generational accommodations. Private chefs can prepare special dinners, and the rest of the hotel’s venues and amenities, such as a heated outdoor pool, sauna, spa, and dining venues, are next door. There’s a complimentary house car and shuttle for venturing out, plus s’mores by the firepit and gratis wine each evening.
Japan
Most trips to Japan begin and/or end in Tokyo, where families have plenty of cultural attractions to enjoy, such as the traditional buildings and food stands of the Asakusa district.
Photo by Geoff Haggray
It’s far-flung, yes, but Japan is one of the easiest places for all ages to get around and enjoy themselves, not least because it’s a safe, clean, and vibrant country with great public transportation—Japanese bullet trains are a blast for everyone. You can expect fascinating, enticing culture and, naturally, delicious food—from teppanyaki and tempura to ramen and udon, plus sushi, and much more—across Japan. For kids specifically, there’s lots to see and do, including Tokyo Disney Resort, Universal Studios Japan in Osaka, and Legoland Osaka for theme park experiences, as well as feeding Nara’s deer or canoeing beneath Mount Fuji for more local ones. A fun itinerary can combine an intriguing city stay with an idyllic natural escape.
Where to stay
Six Senses Kyoto
In a walking-friendly part of downtown Kyoto, this new-in-2024 Six Senses has just enough of a resort vibe to ensure your group feels like they’re on holiday. The modern-meets-traditional three-bedroom penthouse suite can hold a few generations on its own for explorations of the city, temples, and geisha district. The property includes a cute kids club and an Earth Lab where adults can join kids in crafting sustainable treasures inspired by Japanese arts.
Rosewood Miyakojima
Minimalist magic is what you’ll find at this Okinawa Islands resort with two perfect beaches, 55 pool villas, ocean-view restaurants serving memorable cuisine featuring local spearfisherman’s seafood (and top-notch pasta), and water so pretty it has its own name, Miyako Blue. Reserve a couple of the two-bedroom houses for a large family gathering and have chef-prepared barbecues under the stars, learn the local style of pottery, and charter a catamaran for sailing and snorkeling.
Kenya, South Africa, and Tanzania
The free Warriors Academy at Saruni Samburu offers guests experiences such as spear throwing, learning to make a fire in the bush, and visiting a local village.
Photo by Andrew Howard
An African safari is one of the most rewarding and indelible journeys a family can take together, because it not only produces once-in-a-lifetime experiences—no two days in the bush are the same—but also inspires younger generations to care more deeply about the planet and its creatures. For seniors in the group, taking their offspring and their offspring to Africa might fulfill a lifelong dream of up getting close to wildlife—with the added benefit of doing so as a family—to witness elephants, lions, or giraffes in their natural habitats. Across the continent are welcoming family-friendly camps that cater as well to adults (even those with mobility limitations) as they do little ones.
Where to stay
Tswalu Tarkuni Lodge
Hidden in a valley amid Tswalu Kalahari’s 292,000 acres of stunning South African Kalahari Desert wilds is this exclusive-use safari camp comprising five suites plus a library, several bars (and a wall of wine), a pool, outdoor dining, firepit, and private spa room. Best of all, the homestead comes with its own dedicated guide, tracker and vehicle, and a host and chef, all ready to fulfill your loftiest aspirations each day by orchestrating unforgettable encounters, meals, and moments that speak to every member of the family.
Saruni Samburu
For an immersion into Samburu culture alongside Kenya’s abundant wildlife, look to this intimate safari lodge of six villas, which can be bought out for a large multi-gen gathering. Community-based conservation is the model and safaris here are anything but monotonous drives in search of animals. Families experience so much personality, especially when partaking in the free Warriors Academy day in the life experience, which includes instruction in throwing a spear, shooting a bow and arrow, making fire in the bush, and visiting a local village.
Singita Milele
In Tanzania’s Serengeti, this five-bedroom residence is the newest option for an exclusive-use safari villa, and its name, aptly, means “forever,” in Swahili. That’s how long the memories will last when a family takes over the uniquely designed suites; shared living space includes a cinema room, fitness center, wine cellar, outdoor boma with firepit for stargazing or starlit storytelling, and multiple heated pools. You get dedicated field guides, chefs, and a host, plus flexible timing for game drives, guided bush walks, and other nature-based activities. There is no minimum age except for bush walks, for which you have to be at least 16.
London, United Kingdom
Gather the generations and hit the sights and the shows in London.
Courtesy of Igor Sporynin/Unsplash
City holidays as a large multi-gen crew can pose challenges, but for families with lots of independent members, or those with varying interests, London is an excellent choice. There’s ample culture, from world-class museums to all the theaters (Savoy and Lyceum to Royal Opera House); a show at one of them could be the impetus for an entire trip. You can add in such standards as Westminster Abbey, the London Eye, and Buckingham Palace, and some might be thrilled with a Harry Potter tour or cruise on the Thames.
Where to stay
One Aldwych
Covent Garden’s sumptuous boutique hotel has a four-bedroom offering, the Somerset Suite, in which the concierge provides mini bathrobes and slippers, rubber ducks, and additional amenities for the smallest members of the family. The minibar full of complimentary snacks is another selling point. This is a well-located jumping-off point for explorations—with shows within walking distance—but also offers its own fun, including a Charlie & the Chocolate Factory afternoon tea and a scavenger hunt through Covent Garden.
Mexico’s Pacific Coast
Four Seasons Tamarindo is a family-friendly paradise perched above the Pacific Ocean.
Courtesy of Four Seasons Tamarindo
Some of the world’s most family-friendly destinations are on Mexico’s gorgeous Pacific Coast, where soft, sandy beaches and cerulean waters perfect for snorkeling and surfing are the definition of paradise. Large, safe, and secure resort developments with abundant dining and activity offerings take all of the work out of planning and trying to please everyone, but there’s plenty of adventure and culture available, too.
Where to stay
Four Seasons Resort Tamarindo, Mexico
When your crew is at least a dozen strong and “beach” is the only thing everyone can agree upon, there’s the Tamarindo Panoramic Five-Bedroom Villa with infinity pool, perched above the Pacific Ocean within a generously sized nature reserve/luxury resort. Experiences to enjoy together include from scavenger hunts and quesadilla-making classes to bountiful breakfasts at a giant live-edge wood table at Rancho Lola, where all members of the fam can eat and drink their hearts out before petting the farm animals and planting a tree together.
Punta Mita Rentals
A 1,500-acre private peninsula north of Puerto Vallarta is home to Punta Mita and its three resorts plus many condos and residences, meaning there are almost limitless options when uniting the family for a big, raucous reunion. To have more independence, book a two- or three-bedroom apartment or an opulent villa with up to eight bedrooms and call in a private chef as needed for amazing meals. There are beaches, golf, dozens of restaurants, shopping, and multiple spas within the development. Also within Punta Mita, family members can come together to learn to eFoil surf (on an electric hydrofoil board) or help release baby Olive Ridley sea turtles.
Northern Italy
Hot tip: While Forestis is an adults-only nature retreat in the Dolomites, the property’s five-bedroom villa allows kids.
Courtesy of Forestis
Extra planning may be necessary to jet off to northern Italy, but once you’re there you’ll be rewarded with glitzy lakes, Venice, Bologna, and Turin, and the impressive Italian Alps and Dolomite mountains. In short: ample memorable ways to spend time as a family. For winter lovers, the 2026 Winter Olympics in Milan and Cortina d’Ampezzo might be the perfect time to visit a region with extraordinary natural beauty and food. In summer, it’s all about experiences on or in water.
Where to stay
Lefay Resort & Spa Lago Garda
This heavenly resort overlooking Lake Garda—Italy’s largest fresh-water lake with a laid-back vibe and Mediterranean climate—has suites with a two-bed and -bath family option plus a three-bedroom residence with its own infinity pool. Things to do include swimming in the clear lake, e-biking, hiking, exploring lemon groves, picnicking and, of course, taking boat trips.
Grand Hotel Villa Serbelloni
For a glamorous Lake Como stay with all the Old World flourishes and dramatic decor, this is the hotel for a family who appreciates a true sense of place. Book the Franz Liszt Imperial Suite of five adjoining rooms (and 3,659 square feet) for the ultimate home base from which to relax at the Beach Club, decompress at the new spa, play tennis or squash, get gelato in the village of Bellagio, or hire a boat for jaunts to the lake’s charming towns.
Forestis
Although Forestis is an adults-only nature retreat in the Dolomites, the property’s new five-bedroom villa—all contemporary Italian cool and exceedingly cozy—is the one way to “sneak in” kids. It comes with a custom-stocked kitchen, entertainment zone for private movie nights, heated indoor-outdoor pool, and 24-hour butler; you also have access to a private guide, driver, and coach for activities like hiking and yoga; and your own chef is available for cooking classes and pizza parties. Expect surprises that go above and beyond, too, from tent setups to theme nights.
Turks and Caicos
Turks and Caicos is an ideal destination for families craving beach and water time.
Photo by Renise Peters/Shutterstock
The 40 islands that make up Turks and Caicos, between the Dominican Republic and the Bahamas, offer peak Caribbean experiences: calm turquoise water, powdery sands, notable marine life, and a laid-back energy that everyone, regardless of their age, should enjoy. The islands’ many resorts, especially in Providenciales (aka Provo), are very well-suited to families, with water sports, kids programming and entertainment included in stays; there are also luxury villas that can be customized to meet a large group’s needs.
Where to stay
Grace Bay Resorts
The perfect blend of resort and private villa experiences is available at this premier Turks and Caicos operator’s properties, which include the recently renovated Grace Bay Club with expansive beachfront suites and a new beach club. The Private Villa Collection portfolio has sleek estates that go up to a whopping 13 bedrooms, almost like miniature hotels. Take one over and you’ll get a personal butler, daily beach setup, and non-motorized water sports equipment.
Beaches Turks & Caicos
Stretched out along a pristine beach in Providenciales, this all-inclusive resort with four-bedroom accommodations is like the promised land for families who love all things water related—and who want flexibility and freedom, too. In addition to a 45,000-square-foot water park within the resort, there are 17 pools, and more than two dozen dining venues, and an unlimited-use policy on PADI-certified scuba diving, windsurfing, and kayaking. Little ones should adore the Sesame Street partnership, and the resort specializes in being sensory friendly, with quiet spaces and further amenities catering to autistic guests.
Amanyara
With villas up to six bedrooms in size, and the largest having private chefs, this resort becomes an ideal place for expansive families to gather in exceedingly elegant island environs. Within an 18,000-acre nature reserve with a half-mile creamy sand beach, it’s all about being outdoors together, in various combinations of generations. You can try water sports including snorkeling, learning traditional handicrafts, joining sailing academies, and exploring through the on-site Nature Discovery Centre aimed at kids of all ages, with special programming for teens.
