Top 10

The Top 10: Fun Ideas for a Multigenerational Vacation

Family journeys offer precious opportunities to bond and experience new thrills together, be it heli-skiing in Iceland or road-tripping down Highway 1 in Big Sur. So if a get-together is on the horizon, we encourage you to carve out some time to review your travel bucket lists, pitch ideas and plan a multigenerational vacation that will bring everyone together. To inspire your crew, we have outlined ten types of trips that are especially conducive to gatherings of family or friends, from a safari in Tanzania to a luxe Caribbean villa rental.

Contact Indagare to speak with a trip designer about planning a multigenerational family trip with a customized itinerary.

Wilderness Ranches and Nature Retreats

America’s Wild West

beckons with its evocative history and opportunity for adventure. Montana's The Ranch at Rock Creek is a five-star summer camp for all ages with activities such as horseback riding, clay shooting and hiking, plus lavish cabins and tented accommodations. In Jackson Hole, the luxurious and family-friendly Four Seasons is the perfect spot for youngsters to enjoy easy hikes and pony rides, while older family members can embark on white-water rafting trips and fly-fishing. For those seeking adventure a little further afield, British Columbia’s Clayoquot Wilderness Resort offers a unique tented experience in a magnificent setting, with excursions such as zip-lining, paddle-boarding in an estuary and a wildlife cruise.

Related: Adventure Travel with Kids

American Family-Friendly Resorts

[caption id="" align="alignnone" width="620"]The swimming pool at Cliff House hotel in Maine The swimming pool at Cliff House[/caption]

When to Go: Year-round Who It’s Right for: Multigenerational vacations for families with members of all ages, who are looking for lots of on-site activities

A classic choice for a multigenerational getaway is a large resort that can entertain everyone on-property. Some of our favorites range from Meadowood in Napa, where family members can hike or ride in a hot air balloon (and adults go wine tasting), to Blackberry Farm in Tennessee and Sea Island in Georgia. These crowd-pleaser properties have an endless menu of activities, events and daily excursions to keep families busy and bonding. Other iconic choices include sprawling beachfront resorts that are perfect for winter getaways like the Four Seasons Hualalai or The Breakers. For summer vacations, we recommend Ocean House in Rhode Island, Cliff House in Maine and Hudson Valley’s Mohonk Mountain House.

In our members' words: "Blackberry Farm was magnificent in every way. The food was superb, the activities were over the top and there was something for our whole family! It was a spectacular few days of major memory-making for all of us." ~ Jim and Audrey Foster, members since 2014

Related: Multigenerational Trips

Family Road Trips

One of the most efficient–and fun–ways to cover a lot of ground is by embarking on a classic family road trip, with stops along the way at scenic lookouts, historic sites and luxurious accommodations. Some of our favorite routes include Big Sur—a gorgeous sweep of the Pacific Coast Highway—where families can visit the charming towns of Monterey and Carmel-by-the-Sea. Carmel Valley Ranch, a beloved family property surrounded by ancient oaks, fields of lavender and a vineyard, keeps sporty families entertained with multiple pools, an 18-hole Pete Dye-designed golf course and a sports center. Another favorite destination to explore by car is Ireland’s Wild Atlantic Way, a picturesque coastline of wind-whipped cliffs, grazing sheep and storybook villages. Begin in the northwestern county of Donegal, with a drive to the mighty Slieve League Cliffs, and cap off the trip at Ashford Castle or Adare Manor, two magnificent castle hotels with falconry, archery and golf.

In our members' words: "Ashford Castle is definitely a something-for-everyone place. Our rooms were beautiful, and the setting was gorgeous. Our family did one activity after another, from mountain biking and falconry to horseback riding and golf." ~ N.B., member since 2009

Related: Top 10: Road Trips

The Caribbean

[caption id="" align="alignnone" width="620"]Pool at Parrot Cay in Turks and Caicos Parrot Cay, Turks and Caicos[/caption]

The Caribbean has long been a favorite family destination thanks to its calm beaches lapped by clear waters, laid-back island vibes and ultra-luxurious resorts. Antigua’s Curtain Bluff, a classic, all-inclusive resort set on a scenic peninsula, has recently undergone a $13-million renovation, and now features refreshed suites and common spaces. Similarly, Parrot Cay in the Turks & Caicos is ready to welcome families after revamping its accommodations and adding a new kids’ club and gym. St. Lucia, known for its dramatic, lush landscapes and adrenaline-fueled activities, has upped its luxe factor with Sugar Beach’s recently unveiled four-bedroom beachfront villas. And for those looking for ample space and privacy, the Indagare Bookings Team can help find the best villas on islands like Harbour Island and Mustique that are perfect for large gatherings.

Related: Family-Friendly Caribbean


When to Go:

December-April Who It’s Right For: Active families who are ski and snow enthusiasts

Skiing is a life-long sport that families can enjoy together, and many of our favorite mountain resorts have excellent ski schools to train little ones. One of Indagare’s favorite family ski destinations, Deer Valley, draws multigenerational groups to the Stein Residences at the classic Stein Eriksen Lodge. These spacious ski in/ski out condos and homes, ranging from two- to six-bedrooms, are the perfect base for large families to relax in style and privacy while getting the best of the resort experience. Another unique U.S. ski experience can be found at Scarp Ridge Lodge, an Eleven Experience property that elevates the ski trip to an entirely personalized adventure, with back-country skiing options and chic lodge accommodations in Crested Butte, Colorado. And thrill-seeking advanced skiers with older children should visit Deplar Farm, a remote, five-star retreat in northern Iceland that offers unparalleled heli-skiing.

Related: Top 10: Ski Lodges

European Resorts

When to Go:

May-October Who It’s Right For: Families looking for a mix of history and relaxation

Europe’s tapestry of countries and cultures make it a prime destination for a multigenerational gathering. A family trip here can begin in a capital cities, like London, Paris, Rome or Athens, with their history-rich settings and dynamic food and art scenes, before venturing out to coddling resorts. Families desiring a beach sojourn with lots of kid-friendly amenities will adore Mykonos’ Santa Marina or the Marbella Club in Spain, while those wanting a mountain experience can hike and zip-line near Mont Cervin Palace in Zermatt or Schloss Elmau, a grand Bavarian retreat not far from Munich. Another great option is renting a villa in Provence or Tuscany, many of which offer amenities like babysitting and personal chefs.

Related: On the Road with Kids...Aged Six to Eleven

African Safari

[caption id="" align="alignnone" width="620"]Outdoor dining area at Singita Serengeti House in Tanzania Singita Serengeti House, Tanzania[/caption]

When to Go: Year-round Who It’s Right For: Adventurous families with older children (many lodges have minimum ages)

Safaris deliver a distinctive kind of bonding—the absence of cell service and the presence of exotic wild animals like elephants, cheetahs and giraffes bring children, parents and grandparents into a closer communion. The childlike wonder in seeing the vast plains of the Serengeti or Table Mountain presiding over Cape Town’s harbor is made all the more special when surrounded by family. Singita Serengeti House in Tanzania is a stylish retreat available for full takeovers with a swimming pool, tennis court, gym and spa suite in the midst of the savannah. For families wanting ample activities and a kids’ club, the trusted Four Seasons brand also has a Serengeti property with spacious tent suites and coddling service. In South Africa, Royal Malewane’s Africa House is a spacious exclusive-use option with six bedrooms in the bush, and Cape Town's Belmond Mount Nelson can arrange visits to Robben Island and time with Nelson Mandela’s former prison guard, a meaningful experience for the whole family.

In our members' words: “Serengeti House was spectacular, and the staff was so kind. Having a large family has always made it slightly more challenging to plan a vacation, but Indagare helped us create a dynamic adventure in Tanzania that catered to everyone.” ~ The Richard family, members since 2016

Related: Families on Safari

Far-Flung Adventure

[caption id="" align="alignnone" width="620"]Alpine Lodge at Minaret Station in New Zealand Alpine Lodge at Minaret Station, New Zealand[/caption]

When to Go: December-April Who It’s Right For: Families that want intense adventures in spectacular landscapes

Whether you dream of landing in helicopters atop glaciers or trekking through untouched jungle, there are far-flung destinations that offer once-in-a-lifetime adventures for everyone. Adrenaline junkies will be awed by the varied landscapes of New Zealand’s South Island, where travelers can visit fjords, beaches and glaciers all in one day and stay at remote lodges like Alpine Lodge at Minaret Station, which is only accessible by helicopter. Other ultimate adventure destinations beloved include Lizard Island in the Great Barrier Reef for the world’s best snorkeling and diving, Nihi Sumba in Indonesia for top-notch surfing and cultural immersion and Miavana in Madagascar for beach exploration.

In our members' words: “Our family was in heaven at the Great Barrier Reef. We chartered a boat to go to the outer reef, and our expert captain guided us to a spot where we snorkeled with reef sharks.” ~ Shelby Butterfield, member since 2015

Related: 5 Ultimate Wilderness Vacations

Far-Flung Tropical Relaxation

When to Go:

December-April Who it's right for: Families looking for the pinnacle of island luxury and privacy

On these far-flung islands, castaway dreams are realized. Fiji’s Laucala and French Polynesia’s The Brando beckon with ultra-luxe accommodations, an eco-friendly ethos and aquatic adventures in unspoiled reefs and gorgeous lagoons. For families looking for the ultimate splurge, the Maldives has upped the ante with a new Four Seasons private island that houses three expansive villas sleeping up to 22 guests. Families on safari in Africa should tack on a few extra days to unwind at beach properties like Frégate Island in the Seychelles, which has an excellent kids' club and sprawling villas, and Thanda Island, an exclusive-use isle that combines a Robinson Crusoe vacation with world-class luxury off the coast of Tanzania.

In our members' words: “The Brando is over the top. I think I may have died and gone to heaven. The staff was so accommodating to all of my children’s requests, no matter how small!” ~ L.F., member since 2017 

Related: Indagare Matchmaker: Post-Safari Beach Destinations

Yacht Charter

[caption id="" align="alignnone" width="620"]Aerial view of motorized yacht in water off of Corfu in Greece A private charter in Corfu, Greece[/caption]

When to Go: June-September (Mediterranean), December-April (Caribbean) Who Should Go: Independent families that want the freedom of creating their own itinerary on the water

Offering privacy, flexibility and adventure, chartered boat trips are great ways to discover off-the-beaten-path destinations with your family. Yachts and catamarans can be staffed with chefs and instructors to provide five-star amenities in popular cruising destinations like the Mediterranean coastlines of Greece, Croatia and Italy or though the sandy isles of the Caribbean. Families can stop off at various harbors according to their interests and explore uninhabited islands and pristine beaches.

In our members' words: “We want to preserve and cultivate a family connection through memorable experiences. Through Indagare, we discovered that yachting allows us to be on the water surrounded by beautiful settings and share every meal as a family.” ~ Maria Negrete, Indagare member since 2015

Related: Top 10: Yacht Charters

Published onFebruary 26, 2019

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