Multi-Generational Travel Destinations

Making Memories: The Best Luxury Hotels for Multi-Generational Travel

Embarking on a journey that caters to every generation can be a task in itself. But fear not, we are here to curate an exclusive list of the finest luxury hotels perfectly tailored for multi-generational travel. Drawing upon our extensive expertise as seasoned travel advisors and the invaluable feedback from our cherished clients, we’ve handpicked a selection of opulent retreats that promise an exceptional experience for everyone, from the wise matriarchs and patriarchs to the spirited grandkids. Join us as we traverse through 10 of the most exquisite resorts, scattered across the idyllic landscapes of Hawaii, the Caribbean, Mexico, and the United States. Each destination promises abundant activities, ensuring your family reunion becomes an unforgettable, seamless affair.

Aloha to All Ages: Hawaii

Four Seasons Maui at Wailea

Often our highest-selling hotel in the world, Four Seasons Maui has a strong following of loyal fans, and our clients often return year after year, especially those with younger kids.

If you’re traveling with children, the complimentary Kids For All Seasons program is a game-changer, offering a wealth of complimentary activities for the younger ones. For tweens and teens aged 9 to 17, professional counselors skillfully engage and entertain young “campers” at Camp Manitou.

For the adults, the options are equally enticing, with a world-class golf course, opportunities for sailing, surfing, fishing, tennis courts, rejuvenating spa treatments, private helicopter tours, and more. You can also unwind at the secluded adults-only Serenity Pool, which offers elevated panoramic views of Lanai and the West Maui Mountains from its infinity edge. Read a full list of activities on the Four Seasons’ website.

The generously spacious rooms provide ample comfort and are ideal for family bonding. For the ultimate Pacific Ocean views, we highly recommend the Deluxe Ocean-View rooms, which sleeps 4.

Pro tip: If your trip only allows for time on one island in Hawaii, Maui is a great choice because it offers a little bit of everything. The activity selection is broad, and your family can enjoy beautiful beaches, quality snorkeling, great hikes and drives, good shopping, and excellent dining!

As a Top 30 advisor globally for Four Seasons, we can extend exclusive amenities to our clients.

Four Seasons Resort Hualalai

Alongside Maui, to no surprise, Four Seasons Hualalai is also one of our top-selling hotels in the world.

Hualalai stands out as our personal favorite among the Four Seasons hotels in Hawaii for families, thanks to its extensive kids’ club with both indoor and outdoor spaces and a rich schedule of activities to ensure the little ones, aged 5+ are always delighted. For tweens and teens aged 9 to 17, professional counselors skillfully engage and entertain young “campers” at Camp Manitou. Meanwhile, adults can relish in golf, outrigger canoeing, tennis, snorkeling, waterfall hiking, adults-only Palm Grove Pool, ziplining, and more, making it a multi-generational destination that caters to every family member’s desires. Read a full list of activities on the Four Seasons’ website.

A Villa for the Entire Family

The two-story Makaloa Villas are secluded and spacious with three to five-bedroom configurations – perfect for family stays. Make lasting memories on your private patio, complete with a lounge, pool, and fire pit. This home away from home sleeps up to 10 guests, including up to 5 children. Contact us for pricing and availability.

Pro Tip: Adventurous families visiting the Big Island can think BIG for their activities! See a live volcano with a hot lava flow, take a helicopter ride for skiing and surfing on the same day, spend the night snorkeling in the dark with Manta Rays, join the locals, and go cliff jumping… this island is everything except boring!

As a Top 30 advisor globally for Four Seasons, we can extend exclusive amenities to our clients.

Exclusive Promotion: You don’t want to miss this one! For a limited time, receive a guaranteed room upgrade at Four Seasons Maui or Four Seasons Hualalai exclusively through Ourisman Travel or other Four Seasons Preferred Partner clients. Offer is available for new reservations for travel from May 29, 2023, to May 31, 2024. Offer is based on the availability of the upgrade category at the time of booking and does not include Specialty Suites and Villas. Blackout dates include December 17, 2023, to January 3, 2024. We recommend booking ahead given that this offer provides considerable savings and will be subject to availability. This promotion also still combines with all of the other amenities we can offer. Contact us to learn more.

Sailing Through Generations in the Caribbean

Dorado Beach, A Ritz Carlton Reserve

Dorado Beach, a Ritz-Carlton Reserve offers a diverse range of activities that ensures that every family member, regardless of age, finds something to engage and delight them. Created to carry on his family’s tradition of ocean conservation and education, Jean-Michel Cousteau’s Ambassadors of the Environment Program inspires guests to connect with the world around them in hopes that they will work towards preserving it for future generations. Younger kids aged 4 to 8 participate in fun and educational games, hands-on activities, and experiments that impart knowledge about Puerto Rico’s history, native culture, and environment. Older children aged 9 to 16 are treated to custom experiences like creating snacks from the chef’s garden, stargazing to observe constellations in the night sky, and learning about nocturnal creatures. Families with older children, aged 9 and above, have the opportunity to deepen their understanding of the environment through activities like snorkeling among vibrant coral reefs, exploring underwater photography, and embarking on forest hikes.

Dorado Beach also launched a Summer Camp for kids in 2020 where each attendee will get a full itinerary of fun along with a private counselor to explore the resort’s 1,400 acres and beachfront access. The program can range from four days to four weeks.

For the adults, the resort boasts two golf courses, a family-friendly waterpark, tennis courts, and two expansive swimming pools, ensuring that families of all ages can revel in cherished moments and create lasting memories together.

Families seeking the perfect home away from home can choose from the 29 Reserve Residences, providing direct beach access and proximity to the resort’s guest facilities. These spacious residences boast full kitchens, living areas, and up to 5 bedrooms, making them ideal for families looking for comfort and convenience. For those who prefer not to cook, the option to hire a private chef ensures delectable dining experiences. For an even more exclusive retreat, Su Casa, an 8,000-square-foot estate with its own full-sized pool, accommodates larger groups with unrivaled luxury. Use our complimentary booking tool to book yourself or contact our team to learn more about pricing and availability and exclusive amenities that we can offer.

Four Seasons Nevis

The Four Seasons Nevis is the perfect beachfront oasis for a luxury getaway. Last June, Four Seasons invited Ourisman Travel, a top 30 Preferred Partner agency, to experience this peaceful hideaway firsthand. 

For large families or groups, the resort has over 50 residences, villas, and estate homes. The Sunset Hill Villas are ideally situated higher on Nevis Peak, offering breathtaking views of the Caribbean Sea and the island of St Kitts. For guests who prefer to be close to the beach and enjoy modern decor, Pinney’s Beach Villas will be the perfect fit. The resort also offers complimentary meals for children five years old and under at all restaurants. 

There is no shortage of activities while in Nevis. Guests of Four Seasons Nevis can enjoy non-motorized watersports, catamaran cruises, local history tours, mini golf or eco-bio golf, watch and interact with sea turtles, a private beach and pool cabanas, and complimentary monkey-spotting tours for all animal lovers. And of course, the Kids for All Seasons (KFAS) is complimentary and a must with younger kids ages 3 to 9. Drop the kids off for supervised activities that range from learning about local animals to books, games, painting, and scavenger hunts while you enjoy a little well-earned time for yourself. 

Pro Tip: To get the most out of the island, we recommend a 5-6 night stay. This will be enough to enjoy the dormant volcano views, great food, a dreamy town, and a five-star guest experience at the Four Seasons resort. Use our complimentary booking tool to learn more and book now.

Stars, Stripes, and Family Delights: USA

Montage Palmetto Bluff

Montage Palmetto Bluff is the perfect destination for a family reunion, exuding the warm embrace of southern charm and hospitality while whisking you away to a timeless realm where relaxation reigns supreme. Spread across the property are 30 charming stand-alone cottages and 2-5 bedroom residences, offering a cozy retreat for large families of all ages.

The resort is a haven for both adventure seekers and those seeking tranquil pastimes, with bikes available for every guest to explore the network of paved paths. For a more expedient exploration, each room offers the option to rent a golf cart. Small shops adorn pathways, and various docks invite guests to fish, swim, kayak, or charter a boat with a knowledgeable captain—an essential experience in our opinion. Navigating the waterways with a seasoned low-country captain like Boo reveals the region’s captivating wildlife, including a mesmerizing glimpse of a mother dolphin teaching her baby the unique “strand” fishing technique. The resort presents a plethora of activities for kids, from fishing to roasting s’mores, hiking scenic trails, and spotting local wildlife, each rewarded with merit badges that allow children to collect evidence of their adventures and achieve the esteemed ‘Gilbert the Gator’ status upon completing all 12 achievements. Let our Hotel Plus team help secure your activities and reservations or book now using our Hotel Only booking tool.

Montage Deer Valley

Montage Deer Valley in Park City, Utah, stands as one of our favorite destinations for multi-generational travel, especially for those seeking winter thrills and a vibrant Main Street experience. Nestled within the renowned Deer Valley ski resort and atop Empire Pass, its location is simply breathtaking. With ski-in and ski-out access, along with complimentary ski storage, Montage Deer Valley ensures a seamless skiing experience. Families can partake in a variety of nature-inspired activities year-round, from family yoga and guided nature hikes to archery lessons, horse-drawn sleigh rides, blanket picnics, and outdoor concerts. Kid can The cherished tradition of nightly S’mores around the fire pit adds a touch of warmth to every season. For indoor family fun, Daly’s Pub & Rec offers dart games, bowling, and arcade games.

Paintbox is Montage’s exclusive children’s program, which entertains young guests ages 5 to 12 with a happy mix of games, crafts, movies, snowshoeing and mountainside scavenger hunts. Montage Deer Valley also invites kids to a re-imagined camp experience in the summertime with their Camp Compass program for guests ages 5–12, where children enjoy excursions ranging from hiking and barn picnics to crafts and animal tracking. Young guests at Montage Deer Valley can also collect 12 different Montage Merit Badges for a wide range of proficiencies, from catching a fish on fly to scoring a bulls-eye in archery. Upon achievement of all 12 activities, the guest will be awarded with the over-sized, silver ‘Monty’ pin, which signifies that the guest has ‘conquered’ the mountain.

For accommodations, we highly recommend The Vista View Three Bedroom Suites, which all come with private balconies or patios offering breathtaking views of the mountains. With a range of bedding options, these suites can comfortably accommodate up to 11 adults, ensuring ample space for everyone to unwind and make cherished memories together. Contact our team to learn more about pricing and availability during your desired dates or take advantage of our complimentary booking tool. If you’re planning a ski trip, you can also read our blog for our top 5 ski-in and ski-out destinations in America for comparison.

Four Seasons Orlando at Walt Disney World Resort

Four Seasons Orlando stands out as a premier destination for multi-generational travel, offering a family-friendly atmosphere for guests of all ages, and in our opinion, a perfect place to bring the grandparents along too! The Golden Oak View Suite, with its ample space, two bathrooms, and well-appointed living area, is an excellent choice for families, complete with a master suite boasting a luxurious King-sized bed and a convenient walk-in closet.

The resort’s crown jewel lies in its abundance of pools and water attractions, including the lazy river and the expansive five-acre water park known as Explorer Island, guaranteeing endless hours of fun. Families often choose to dedicate a day here, opting for one less day at Disney. For younger children, the complimentary Kids For All Seasons (KFAS) club offers a range of engaging activities, while older kids can escape to “The Hideout” for video games and pool tables. Parents can also take advantage of the complimentary kids camp for some well-deserved relaxation. The kids’ pool features a giant TV screen for “swim-in-movies” showcasing beloved Disney films, adding an extra touch of magic. Adults seeking quiet time can retreat to the serene adults-only pool, while the spa offers a range of indulgent treatments, including the popular “Mommy and Me” princess makeover. Dads can enjoy a few hours of golf at the Tranquilo Golf Club, a par-71, 6,901-yard course designed by Tom Fazio, catering to all skill levels.

For more Disney-themed activities, guests can enjoy a character breakfast with Goofy & His Pals on Thursdays and Saturdays. For those seeking unique Disney experiences, the Four Seasons Orlando offers a Disney Planning Center where you can arrange private, guided VIP tours of the parks. You can also participate in activities like Mermaid School, where children can make their Little Mermaid dreams come true in a small group located at Yacht Club, Caribbean Beach, and Art of Animation. We recommend booking your class at the Yacht Club for the best pool. Learn more or book now.

Viva la Familia: Mexico


Montage Los Cabos

Montage Los Cabos stands as the epitome of a five-star destination, seamlessly catering to families, making it an exceptional choice for multi-generational travel. Nestled along the coveted Santa Maria Bay Beach, this luxurious resort offers direct access to a swimmable beach that doubles as a playground for outdoor enthusiasts of all ages and a haven for marine life, making it ideal for family snorkeling adventures.

The resort has three large pools, providing endless opportunities for relaxation and soaking in the salty breeze. Montage Los Cabos showcases well-appointed amenities, including the indulgent Spa Montage, a Fitness and Movement Studio, the engaging Paintbox Kid’s Club catering to children aged 5-12, and an 18-hole golf course.

There are three private homes to choose from, sleeping between 8-12 guests. Each home comes with private butler service, daily breakfast prepared by the resort’s chef in the Casa, family BBQ night once per stay, and so much more. Our team can expertly help you decide which Casa is best suited for your family’s needs. Already know what you want? Take advantage of our complimentary booking tool on Virtuoso and still receive all the perks.

Four Seasons Resort Los Cabos at Costa Palmas

Four Seasons Resort Los Cabos at Costa Palmas offers an extensive range of activities suitable for multi-generational travel. From snorkeling in the Sea of Cortez to hiking, biking, and ziplining in the Sierra de La Laguna Mountains, there’s something for everyone. Enjoy seven pools, a swimmable beach, and an exclusive marina for water adventures. The resort features an exquisite 18-hole golf course, Costa Palmas Golf Club, with complimentary tacos and margaritas on the course (yes, please). Additionally, a spa, sports complex, and private yacht charters add to the allure, ensuring activities for all ages.

The hotel’s contemporary architecture mixed with native landscaping creates a sanctuary for guests to recharge. Earlier this year, Four Seasons unveiled its newest private retreats collection surrounding the brand’s first ever private marina on the East Cape of Los Cabos. The collection offers two to six-bedroom contemporary residences that seamlessly integrate indoor-outdoor living with flowing spaces, elemental design and native landscaping. The collection offers a wide array of accommodations for up to 18 guests, each with private pools and expansive indoor-outdoor entertainment space. All Private Retreats include access to a personalized butler, a private chef upon request and Four Seasons MANDIL program, which provides guests with fresh and local recipe boxes for dishes such as guacamole and Zarandeado fish. Book now or learn more.

One&Only Palmilla

Located on a private peninsula in Los Cabos, One&Only Palmilla has long been a destination in and of itself for families, couples, and friend groups for years. Rooms and suites are located in stand-alone one and two-story villas, all of which offer ocean views. The villas are well placed throughout the property with privacy for all. The Casita Suites are the highest category before the two villas, Villa One & Villa Cortez, coming with their own private infinity pools and dedicated butlers.

For golf enthusiasts, the 27-hole Jack Nicklaus-designed course with sweeping ocean panoramas and the on-site RoboGolfPro Swing Training facility. A state-of-the-art tennis complex, overseen by internationally trained pros, caters to tennis aficionados. Parents will delight in the exceptional kids club for children aged 4 to 11, where little ones can enjoy supervised activities, providing parents with some well-deserved adult time. Daily beachfront yoga sessions, guided by certified instructors, offer a serene way to start or end the day. The resort’s resident shaman offers transformative ceremonies rooted in ancient practices, providing guests with a deeper connection to themselves and the world around them.

One&Only Palmilla has one of the best beaches in Cabo. The beach is calm and is one of the only swimmable beaches in Los Cabos, great for families with kids who love to splash in the waves. The property has two pools for guests to choose from, Tortuga Beach & Agua Pool. Tortuga Beach is the adults-only pool and is located off of the non-swimmable beach on the property. Agua Pool is a family-friendly pool, close to the KidsOnly clubhouse and the swimmable Pelican Beach. A few floating beds are situated between the two beaches, swinging above the waves and offering stunning views. Be sure to snag one if you see one available – they are not up for rental!

Take a peek at our Virtuoso booking tool for pricing and availability or reach out to our team!

Riviera Maya

Rosewood Mayakoba

With its sleek design and flawless service, the Rosewood Mayakoba is the best fit for our guests with refined taste and a need for larger and more private accommodations. The Rosewood Mayakoba feels exotic, comfortable, and luxurious all at the same moment. There are several suite categories to choose from, but our favorite for large groups is the Lagoon Villas. Generously laid out in two-, three-, four-, or five-bedroom configurations, these private homes sleep up to 12 guests. This is one of your very few opportunities to get an overwater experience without the long flight to Bora Bora or the Maldives!

The resort also excels in family-friendly offerings, with activities such as yoga classes, eco-tours led by knowledgeable biologists, engaging scavenger hunts, eco-bingo, interactive pizza and cookie-making classes, and themed nights like Mexican Night, Pirate Night, Pajama Party, and Mayan Celebration. Spanish and Mayan lessons and captivating Mayan storytelling sessions further enrich the experience for guests of all ages, ensuring cherished memories for the entire family. Rosewood Explorers is a program designed to provide the hotel’s youngest guests with special services, amenities and convenience items designed just for them.

Rosewood Mayakoba doesn’t just cater to young kids. Aquí Me Quedo, meaning “Here I Stay”, is the new, adults-only beach club. Enjoy the quiet amongst multiple pools and grab lunch at La Cantina, a vintage-style food truck serving casual Mexican fare. Once per month during the Full Moon, head to La Cantina at Aquí Me Quedo to discover a lively beach party celebrating the moon’s full illumination over the ocean. Another hot topic is the newest adults-only, hidden speakeasy called “La Isla Secreta”, which offers guests a late-night cocktail lounge amidst the mangroves.

Utilize our Hotel Plus service with assistance in finding the best itinerary for your entire family, or book your stay using our free booking tool and still revel in the perks we can offer as one of our clients. Feel free to take a peek at our reviews of all the luxury hotel options in Mayakoba if you want to know all your options.

Elevate Your Next Family Reunion

We have a wealth of knowledge of places to stay and things to do in the listed destinations above, and ultimately using our Hotel Plus consultative services will help us best tailor your vacation to your family’s preferences. From providing you with consultation resulting in options personalized to your needs to assisting in making arrangements for spa appointments, dining reservations, and transfers, Hotel Plus is designed to elevate the Hotel Only experience.

Already have a trip booked? Worry not! Through a process called a Hotel Reservation Takeover, our team can – you guessed it – take over the hotel reservation, apply our amenities, and support your booking from that point on!

As our client, we can offer exclusive, complimentary benefits to your stay:

  • Complimentary breakfast daily for two
  • Complimentary room upgrade (STA)
  • 100 USD resort credit
  • Early check-in / late check-out (STA)

To get started, email us at or submit a Travel Request Form on our website.

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