Multi-Generational Getaways: Family-Friendly Travel Destinations

exterior, pool, greenery, table
Photography courtesy of Singita.

In search of an award-winning spa for your aunt, a lovely shaded cabana for Grandpa, and an epic horseback riding experience for the kiddos, all in one place? If that seems like a daunting task, you’re not alone. We asked five Scouted travel experts for their top picks for luxury vacation destinations, both domestic and abroad, that prove multigenerational travel can be a memorable—and dare we say—a bonding experience for all parties involved. It’s time to pack those bags. To find a Scouted travel expert, consult The Scout Guide Directory.

Maui, Hawaii 

Photography courtesy of Four Seasons Resort Maui at Wailea.

“My family and I recently took a multigenerational vacation to Maui. I believe vacation begins the moment you leave the house. For long flights, I prefer to fly premium plus or business, which ads comfort for all parties involved, from my parents to our baby(Here’s looking at you lay-flat beds and infant bassinets). I strongly advise seeking airline lounge accessibility during layovers so you can enjoy complimentary food and drink, as well as much larger and cleaner family facilities for those traveling with children. We stayed at Four Season Maui at Wailea (of White Lotus, Season 1 fame) which, hands down, offers the best service on the island. The adults-only serenity pool—a stunning infinity pool with a swim-up bar and the most spectacular views of the mountains and Pacific Ocean—was one of my favorite spots at the resort. Start your day with Duo’s breakfast buffet, and don’t miss the chocolate chip pancakes. We enjoyed many of the complementary activities like yoga on the beach and outrigger canoeing. No trip to Maui is complete without dining at Mama’s Fish House; just make reservations six months in advance. For the kids, rooms were equipped with a sound machine, diaper genie, and a surprise gift on arrival. If you’re inclined to visit West Maui, which offers a somewhat cooler climate and a more secluded ambience, I recommend exploring the newly renovated The Ritz-Carlton Kapalua, where guests can enjoy extensive seaside trails, zip-line tours, and championship golf. I was most excited about the Fire Lanai rooms which feature extended lanais complete with a a fire pit and a special menu to make one’s own tropical twist on s’mores. It’s sure to delight the younger set. – Kate Moore, luxury travel advisor from Melted & Moved in Norfolk, Virginia

Sea Island, Georgia

Photography courtesy of The Cloister at Sea Island.

”‘How did I not know about this place?’ This was my initial thought after first discovering Sea Island, Georgia, in 2019. I later learned that my grandparents had honeymooned there back in the 1940s, right around the same time that George HW and Barbara Bush did. Sea Island has been a multigenerational family favorite for a long time and provides every activity imaginable from golf, tennis, and pickleball, to horseback riding and archery. Sea Island offers a wide range of accommodation options to fit your groups needs, including the main building at The Cloister Sea Island, The Cloister Beach Club, The Cloister Ocean Residences, The Lodge, and Cottages and The Inn at Broadfield. I recommend dinner at Colt & Alison with sunset drinks on the green at The Lodge while listening to the Scottish bagpiper. I love to arrange for a photographer to meet clients there for the perfect golden hour family photos.” – Maria Diego, founder of Diego Travel in San Diego, California

Vermejo, A Ted Turner Reserve 

Photography courtesy of Casa Grande at Vermejo, A Ted Turner Reserve.

“For a domestic trip consider a private national park in New Mexico, Vermejo. There are a wide range of lodging options, but for a truly memorable experience, consider reserving the stunning Casa Grande. This elegant private villa boasts 25,000 square feet of luxurious living space and panoramic views of the sprawling landscape. Activities abound at Vermejo, from guided wildlife safaris to fly fishing, rock climbing, horseback riding, spa services, and starlit stargazing. There’s something for everyone, including the little ones who can partake in educational nature programs. All excursions are private and led by a guide who’ll feel like a part of your family. I recommend arranging for a private family dinner on the veranda of Casa Grande, where a personalized menu showcases the best of Southwestern cuisine.” – Courtney Gardner, owner and founder of Fisher & Stout in Arkansas

St. Moritz, Switzerland

Photography courtesy of Badrutt’s Palace.

“One of my favorite places for multigenerational families who may have some non-skiers in the group is St. Moritz, Switzerland. Due to its elevation, it has the longest ski season in the Swiss Alps, yet because it’s a wide valley, it also gets more sunshine than any other ski destination in Switzerland. While there are many great five-star resorts to choose from, we love Badrutt’s Palace for large families, especially over holidays. For New Year’s Eve festivities, a whopping quarter million dollars is spent on the decor alone. Arriving at St. Moritz is an experience in and of itself. Whether you make your way via the Glacier Express train or by private plane, Badrutt’s Palace will pick you up in a car from their complimentary Rolls Royce fleet to transport you like royalty to your accommodations. For a unique experience, don’t miss St. Moritz’ White Turf races. Nowhere else in the world has horse polo and racing on a frozen lake. Night skiing is another unique experience you won’t want to miss. Kids and grandparents can ice skate, go tobogganing, or take horse-drawn carriage rides through the quaint town. Our kids love pizza at Chesa Veglia, an old farmhouse built in 1650 and a St. Moritz staple. For an apres ski experience like no other, visit Paradiso, where they often have designer pop-ups with Gucci or Louis Vuitton. There is no shortage of Michelin experiences in St. Moritz either, and you’ll find premiere shopping for those looking for something to do while the rest are skiing their hearts out down the Swiss Alps.” – Maria Diego, founder of Diego Travel in San Diego, California

Ambergris Cay, Turks & Caicos

Photography courtesy of Ambergris Cay.

“For your not-so-standard international beach trip, I encourage clients to consider Ambergris Cay, a rustic private island just a short 20-minute flight from Providenciales in Turks and Caicos. Book one of the island’s spacious, luxurious, well-appointed, private villas for your family and you’ll have all the comforts of home. Relax on pristine, white-sand beaches or enjoy an array of water sports, such as snorkeling, paddleboarding, whale watching, bone fishing, deep sea fishing, and kayaking. Explore the island on foot, bike, or golf cart to see Columbus Beach or paddleboard in the calm waters of Monck Beach on the Caribbean side. Don’t forget to look for green sea turtles and pink flamingos, as well as the largest population of rock iguanas. I also encourage families to explore the vibrant marine life further with a private boat tour and picnic, perfect for bonding over turquoise waters.” – Courtney Gardner, owner and founder of Fisher & Stout in Arkansas


Photography courtesy of Zannier Hotels Sonop.

“The most-requested whole family trip is undoubtedly an African safari, as it is on most travelers’ bucket lists. It appeals to almost all ages,though it’s definitely “adventure travel”, it’s perfectly suited for younger and older travelers as most of the trekking is done from the comfort of a game drive vehicle. With camps that are beyond luxurious—think gourmet chefs, daily laundry service, spa treatments, private dinners or even camp-outs in the bush— even the pickiest relative will be hard-pressed to complain. I typically recommend at least 10 nights on the ground, with five to seven nights in the bush in Tanzania, Botswana, Kenya or South Africa. We’ll often suggest starting or ending in a city like Cape Town at the family-friendly Belmond Mount Nelson or in Nairobi at Giraffe Manor, to accommodate international flight times. The age-appropriate and able-bodied travelers in the group may also choose to do a pre- or post-safari excursion like gorilla-trekking in Rwanda at Singita Kwitonda Lodge, or a stay at Zannier Hotels Sonop in the Nairobi desert.” – Lauren Tulp Cichocki, founder of Arbiter Travel Co., Los Angeles, California


Photography courtesy of Ashford Castle.

“Ireland is a lush green country dotted with grazing sheep and medieval castles, with something to do for every age and at a pace that can be as fast or as slow as you’d like to take it. Most visitors want to cover the entire country in a week-long visit, but I’d like to argue that this expansive country requires a bare minimum of two weeks to cover it all. While Dublin is a must-see—I love The Shelbourne and The Merrion Hotel for multigenerational families—I don’t let my clients linger too long because the west coast of Ireland has so much to offer. With properties such as Ashford Castle and Adare Manor, who doesn’t dream of staying in a castle? Ashford Castle provides activities such as falconry, boating, and clay shooting, and for the little ones, they have a Lego butler, customized treasure hunts, and children’s afternoon tea. If any family member is missing their four-legged furry friends at home, they allow you to go for a morning walk with the Castle’s dogs. At the newly reopened Adare Manor, perhaps the most impressive feature is their state-of-the-art golf course, where they spent a million dollars on each hole’s drainage system alone. Worried about the rain? No expense was spared on their indoor Padel Club, where they offer padel courts, an indoor golf simulation room, plus gym and indoor swimming pool. For the foodies in the family, the gastronomic experiences along with the impressive whiskey collection cannot be beat.” – Maria Diego, founder of Diego Travel in San Diego, California

Costa Rica

Photography courtesy of The Springs Resort & Spa.

“One of our top picks for adventure-seeking, nature-loving, and culture-craving travelers is Costa Rica. It is a destination that offers a multitude of activities to suit all age groups and satisfies diverse interests. Visiting at least two different areas with a split-stay is ideal; and the suggested number to visit for the most fulfilling experience is nine to 12 days. You’ll want to Include the Arenal Volcano in your travel plan. This area is mesmerizing and has so much to offer explorers of all ages. The Springs Resort La Fortuna, Arenal is a wonderful choice for family gatherings. While there, make sure to visit the Club Rio Outdoor Center, located directly below the resort along the river. Club Rio has multiple activities, including tubing, kayaking, horseback riding, rock climbing and rappelling, nature tours, fishing, and an animal sanctuary. For the thrill seekers in the family, we highly recommend ziplining with Costa Rica Sky Adventures. From Tamarindo, enjoy a lunch or sunset sail on a private catamaran. The more adventurous may wish to snorkel, while others can relax, and take in the sun, sea, and scenery. For a wide selection of tours and activities, check out Project Expeditions. For a more one-with-nature experience I recommend Rio Perdido Hotel & Thermal River, or The Westin Reserva Conchal, an all-inclusive beach resort.” – Marianne Windham, owner of Windham Travel and Leisure in Huntsville, Alabama

Melted & Moved appears in The Scout Guide Tidewater. Diego Travel appears in The Scout Guide San Diego. Fisher & Stout appears in The Scout Guide Northwest Arkansas. Arbiter Travel Co. appears in The Scout Guide Newport Beach. Windham Travel and Leisure appears in The Scout Guide Huntsville.