Trips among multi-generational families have been on the rise since the end of travel restrictions related to the pandemic. Luxury tour operator Black Tomato reported a 20% increase in multi-generational travel from 2022 to 2023, and The UK’s Daily Telegraph cited 2023 as the year of the six-figure family holiday.
Group trips with extended family or friends are driving popularity in private buyouts or takeovers of properties for wellness or other retreats. For family office members of different generations, spending a few days away together can help smooth transitions and strengthen the bonds of a family. Finding common ground outside the boardroom can be instrumental to more harmonious decision-making and problem-solving.
Planning a trip for people of different age groups and interests can be daunting. It’s helpful to bear in mind the goals of the trip while trying to find a property that offers a range of suitable activities for everyone, a structure for family and free time, setting expectations so everyone’s on the same page.
Here are some of the best destinations for family retreats.
-
U.S.
The Point | Saranac Lake, New York
Originally built in the 19th century as a private retreat for William Avery Rockefeller (John D. Rockefeller’s grand-nephew), The Point is among a group of grand family compounds built on the lakes of the Adirondack mountains. The 11-room, 22-guest, all-inclusive resort sits on 75 acres of lakefront property. Activities include hiking and skiing trails, tailored itineraries, ice skating and ice fishing in winter and watersports in summer, as well as e-bikes, outdoor movie nights and innertube races. Guests have access to an on-site kitchen and fully stocked bars with 24-hour access, seasonal menus sourced from local farms, picnics, campfire s’mores, themed dinner parties and special meals that can be prepared using a family’s own special recipe.
The Resort at Paws Up | Greenough, Montana
The Resort at Paws Up is a family-owned resort and working cattle ranch. Set on 37,000 acres including the Blackfoot River, the resort’s Wilderness Estate is made up of 10 homes, each with three suites. Glamping is also available. The vast grounds make the resort a great location for guided hikes, whitewater rafting, fly fishing, forest bathing, mountain biking, ATVs, horse riding, fireworks and hot-air-balloon rides. Winter activities include snowshoeing, cross-country skiing, snowmobiling, sleigh rides and ice skating.
Families can go on a cattle drive, shoot clays or take an archery course. Wine tastings and intimate musical concerts can be organized as well as hands-on cooking demonstrations and wilderness workshops.
Windy Hill Farm and Preserve | Loudon County, Tennessee
Located on 650 acres in east Tennessee, Windy Hill Farm and Preserve hosts up to 27 guests in a farmhouse with five bedrooms, nine private cabins and eight lodge rooms. Set along two miles of the Tennessee River, Windy Hill has all the trappings of a summer camp for grown-ups, with activities ranging from quail hunting, hiking, garden and orchard walks, beekeeping and honey tasting, axe throwing, archery, biking, kayaking, paddle boarding and fishing to gardening and cooking classes and nightly bonfires. Meals use ingredients harvested on the property. Meeting space is available.
-
CARIBBEAN
Four Seasons Nevis Pinney’s Beach | Nevis, West Indies
The Four Seasons Nevis is a large resort with a separate area for smaller family buyouts called Pinney’s Beach — made up of seven luxury villas that offer in-villa breakfast, dedicated concierge and ambassador, a block party with dinner and a DJ or band, a rum cart cocktail hour, afternoon gelato cart, a sunset catamaran sail, a private beach dinner, team-building activity, beach cabana and a meeting room with catered lunch. Guests have access to resort amenities including three beachside infinity pools (one for adults only), watersports, spa, tennis, pickleball and basketball courts, yoga classes and an 18-hole Robert Trent Jones II golf course. Family barbecue’s and private cooking classes can also be arranged.
Three villas make up Little Harbour Estates on the sheltered southern side of Anguilla looking toward St. Martin. The property is set against Meads Bay and its white sand beach. There are eight bedrooms in The Beach House. Villa Indigo sleeps 20 in 10 suites with a multilevel garden, two pools and a private swimming deck and beach area. Le Bleu sleeps 22 between the main house and garden suites and features two swimming pools and a game/meeting room. Access to tennis and pickleball courts, a cinema room, private chef and villa staff are included. Kayaking, kiteboarding, rum punch trail tours and hikes can be organized. Meals are tailored to guests' requirements, including full kosherization.
-
UK AND EUROPE
Cowdray House | Midhurst, West Sussex, England
Nestled in the South Downs National Park just over an hour from London’s Heathrow Airport, Cowdray House is a historic 16,000-acre estate with landscaped gardens, a lake and woodlands. Grounds include the ruins of one of the most important early Tudor houses. Experiences include polo (lessons available), golf, simulated game shooting, wildlife tours, foraging, gin tastings, art classes, bowling alley, tennis court, cricket strip, croquet lawn, a spa, and indoor and outdoor pools. The estate also offers an evening of stargazing in the International Dark Sky Reserve, with Dr. John Mason pinpointing familiar and unfamiliar constellations and discovering the myths of the stars. Dinner and drinks are prepared using local produce, including meat, eggs and honey from the estate.
Aurora Lodge | Tromvik, Norway
Norway’s Aurora Lodge looks strikingly similar to a lodge featured in the last season of "Succession." Set in the remote Lyngen Alps, it is accessible by car (one hour) or helicopter (25 minutes) from Tromsø Airport, an easy transfer from Oslo. Six suites — sleek, angular, asymmetrical glass boxes with blond wood — face the Norwegian Sea and are the work of Scandinavian architect Snorre Stinessen. Activities, depending on the season, include kayaking with orcas and Northern Lights viewing with specialist photographers — 2024 is slated to be one of the best years for sightings. A fireplace complements the open-plan living and dining room to create a natural environment for afternoon hygge. A traditional sauna and Jacuzzi are outside. Aurora Lodge can only be booked through Black Tomato, which also curates experiences like reindeer sledding, snowmobiling, sea-to-summit skiing and ocean fishing for cod and halibut, with your catch prepared by a chef.
Villa Il Santo | Tuscany, Italy
Opening in May, this seven-bedroom luxury villa sleeps up to 16 people. Originally built in AD 1000 and recently restored, it’s situated in the heart of Chianti, making it a great base for visits to Florence, San Gimignano and Siena. With views over the Tuscan countryside, the property has several spacious living rooms, a heated infinity pool and landscaped gardens with roses, jasmine and olive trees. Activities include helicopter tours of Tuscany, mushroom and truffle hunting, nearby vineyards for wine tasting, a personal sommelier who can teach wine and food pairings, cycling, hiking, swimming, tennis, golf and a beekeeping tour with honey tasting. An outdoor kitchen offers a pizza oven and barbecue. Florence is 40 minutes by car and Pisa 80 minutes.