Here’s a riddle: On vacation, how do you keep grandparents and grandkids happy? Answer: Find a resort that caters to both. But that’s not a simple feat.
That’s why we did the heavy lifting to uncover resorts that will bring a smile to the entire family — parents included. We’ve picked our favorite family-friendly resorts in America and the Caribbean:
CARIBBEAN
Jumby Bay Island
It’s no surprise celebrities like Oprah Winfrey and Justin Bieber vacation on this private, 300-acre island off the northern coast of Antigua. The spectacular Forbes Travel Guide Five-Star hotel’s service and amenities redefine upscale. The 40-room, all-inclusive resort has plenty to do with three pools, four miles of beach, a spa and wellness center, three tennis courts, bike cruisers for every guest, a farm where it grows its produce and restaurants fit for any gourmand.
Adult Perks
- There’s a complimentary ferry to Antigua for exploring Nelson’s Dockyard National Park, a UNESCO Site, or observing the largest frigate bird community in the Western Hemisphere.
- Sailing lessons and reef fishing are two of the unique supplemental activities at the resort.
- Don’t miss the Caribbean cooking classes hosted every week in the property’s display kitchen.
Kid Perks
- For families with kids of varying ages, Jumby Explorers Kids Club offers two programs, one for children ages 3 to 8 and another for ages 9 to 12.
- An unusual offering for all-inclusive kid clubs, those under 3 years old can attend camp with a babysitter or parent.
Insider Tip
- Ideal for larger families, book one of the 12 newly renovated Ocean View suites, available this winter. The outdoor soaking pools stand out, and in larger suites, you’ll have your own pool.
BARBADOS
Sandy Lane Hotel
An opulent pink palace set in ancient mangroves overlooking white sands and azure waters, the Five-Star retreat possesses one of the most distinguished addresses in Barbados, especially after a $280 million renovation. Partake in the four restaurants — like the romantic beachfront L’Acajou — an opulent spa, a 7,500-square-foot pool, a fitness center, three golf courses (including the world-renowned Tom Fazio-designed Green Monkey), nine tennis courts and countless watersports.
Adult Perks
- Arrive at the resort in style with a complimentary airport transfer in one of the hotel’s fleet of luxury vehicles, which includes a Rolls-Royce Phantom.
- The free packing and unpacking service comes in handy for families traveling with little ones.
- Staff members deliver service with a smile at Sandy Lane. You’ll especially appreciate the beach and poolside service that includes Evian water misting, cold towels and sorbets at your whim.
- Make sure to take advantage of the hotel’s grand 47,000-square-foot spa, the largest in the Caribbean.
Kid Perks
- The complimentary Treehouse Club for kids ages 3 to 12 features playground activities, kid’s dinner parties, poolside games and movie nights. The separate teen’s club has video games, a jukebox and even a mocktail bar.
- The Treehouse Club welcomes babies and toddlers accompanied by a parent or nanny.
- In the summer, breakfast and dinner for ages 3 to 12 are complimentary.
Insider Tips
- Arrive at least 45 minutes before your spa treatment to enjoy the soothing amenities, like hydrotherapy pools, a spa garden, a sauna or a relaxation room.
- The dress code leans toward the more upscale, so pack accordingly.
BRITISH VIRGIN ISLANDS
Rosewood Little Dix Bay
An eco-friendly resort since first opening in 1964, Rosewood Little Dix Bay has always put the natural environment at the heart of its design. One of the first Caribbean resorts to promote sustainable luxury, Little Dix Bay sits on 500 acres of Virgin Gorda paradise with white sandy beaches and turquoise waters. With four restaurants; a robust wellness program that includes a spa, two pools, outdoor yoga and a fitness center; a kids club; and much more, the whole family will find something more than suitable.
Adult Perks
- Overlooking the Sir Francis Drake Channel, Sense, A Rosewood Spa embodies the rejuvenating essence of its cliffside environment. Don’t miss the unique Baths Journey treatment that begins with a swim in Baths National Park and ends with body, hair and skin services in the resort’s garden.
- The property’s Rum Room is an open-air lounge that offers an extensive library of rare and aged rums, a global selection of wines, classic cocktails from the 1960s and 1970s and live music. Sample small-batch rums at weekly tasting sessions.
- Hone your game with private and family lessons on six tennis courts and two pickleball courts.
Kid Perks
- Through Rosewood’s complimentary Explorers program, 3- to 9-year-olds will learn about Caribbean culture while connecting with nature. Family-friendly activities include landscape painting, Caribbean folk arts and crafts, West Indian music, local storytelling and jewelry making.
- Families can connect with the tropical surroundings through nature walks, shell collecting, treasure hunts, sandcastle contests and more. Half- and full-day programs are offered, while babysitting and nanny services can also be arranged.
Insider Tips
- If you want the family altogether in one place, book one of the original private historic homes on the resort.
- All ages can support the British Virgin Islands’ commitment to caring for sea turtles at Rosewood Little Dix Bay. Alongside the Association of Reef Keepers, a marine conservation organization, you can learn about the efforts to protect this endangered species while spending time with sea turtles, including monitoring hatchlings and tagging turtles.
UNITED STATES
CALIFORNIA
Rosewood Miramar Beach, Montecito
This celebrity enclave near Santa Barbara feels like a Hamptons getaway with a private beach and train sightings. But it adds in fun family activities like scavenger hunts. The Five-Star hotel has six restaurants and bars, from farm-fresh casual to upscale Italian; an intimate spa; two pools (one adults-only); beachfront rooms; an ice cream shop; and a Goop boutique.
Adult Perks
- With babysitting services available, the Miramar Picnic, with four different champagne themes to choose from, beckons for a romantic sunset memory-maker. Or simply enjoy a dreamy sunset cocktail at the Miramar Beach Bar overlooking the Pacific Ocean.
- The luxury hotel prioritizes a restful vacation for its guests. In 2022, the Five-Star Sense, A Rosewood Spa launched sleep-focused treatments with destination-inspired ingredients like CBD and lavender. As part of its accommodation offerings, Rosewood Miramar Beach also unveiled four Bryte Sleep Suites with specially designed restorative beds.
- Get into the vacation zone with meditative silent mind yoga (you’ll don noise-canceling headphones to hear music and voice instruction) on the beach.
Kid Perks
- The Montecito hotel’s pristine private beach — complete with a personal beach concierge — provides kids of all ages with the ultimate amenity. Teens can paddle or boogie board while toddlers stay busy making sandcastles.
- Although there’s no kids club per se, the resort offers plenty of activities, like a beach bootcamp, arts and crafts, movie time and nightly s’mores-making.
Insider Tips
- The property has many charming garden-facing bungalow rooms, but for an ocean view, book one of the Beach House suites.
- For an activity the family will not forget anytime soon, reserve a session with the resident falconer. You’ll become experts on the cultural heritage of falconry and take home a fun group photo with the property’s hawks.
FLORIDA
The Breakers Palm Beach
A favorite among jet setters since the late 1800s, the Italian-Renaissance-style property sits on 140 oceanfront acres. With four pools, 10 tennis courts, two championship golf courses, an innovative spa, 10 restaurants, luxury shopping, an entertainment center and endless watersports, Florida’s grande dame resort will keep you and your family endlessly entertained.
Adult Perks
- The Four-Star resort’s HMF bar (named for hotel founder Henry Morrison Flagler, who’s also credited for making South Florida a vacation destination) has a hopping scene and regular live music.
- Stay consistent with your fitness routine at the 6,000-square-foot ocean-facing gym with all the latest equipment.
Kids Perks
- The kids can stay active with tennis and golf academies, a mini golf course, a basketball court and bike rentals.
- The Family Entertainment Center includes an arcade with old- and new-school games, along with a video game lounge.
- A 4,500-square-foot playground features slides, tunnels, bridges, puzzles and interactive games. Nearby benches allow parents to supervise comfortably under the area’s sunshades by day or lights at night.
- Guests ages 6 to 15 can enjoy a touch of glamour with chic hair and nail services at the whimsical Spa Petite.
Insider Tips
- Reserve a cabana with a TV, fridge, full bath and concierge to cater to your every whim for the ultimate pool day.
- The cozy Italian Restaurant’s convenient location within the Family Entertainment Center lets parents and grandparents dine while the kids play close by.
- Families will want to book the coveted connecting rooms well in advance.
- Reserve a snorkeling excursion to see an amazing reef, a well-kept secret just a few fin kicks from shore.
HAWAII
Grand Wailea Maui, A Waldorf Astoria Resort
Twenty-five minutes from Maui’s Kahului Airport, Grand Wailea sits on the southwest coast, with year-round perfect weather in the ritzy area of Wailea. The immense Four-Star resort boasts 40 acres of lush tropical landscape along Wailea Beach, luxurious accommodations, delicious cuisine, Hawaii’s largest private art collection, locally inspired spa treatments and a beautiful chapel.
Adult Perks
- Great for a romantic date night, Grand Wailea offers private beach dining under the stars.
- Slated to unveil a reimagined spa experience in the coming year, the resort offers Mohalu by Spa Grande, a private escape for those looking to rejuvenate and relax in quiet comfort with personalized services that connect you with the healing mana (energy) of Hawaii.
- Don’t miss Grand Wailea’s luau with top-notch Hawaiian food and performers.
- The resort is an outdoor museum of more than 900 pieces of art, including a sculpture garden and nine Botero sculptures
Kid Perks
- In addition to Grand Wailea’s serene Adult Hibiscus Pool, the resort houses a kid-friendly water oasis, spanning nine individual pools across six tiers, all interconnected by flowing slides and accompanied by waterfalls and grotto caves throughout.
- Kids, or keiki in Hawaiian, can try locally inspired crafts such as making their own kukui nut bracelets and ti-leaf leis.
Insider Tips
- Dine at the overwater bungalow restaurant, named Humuhumunukunukuapua’a for the state fish, serving Hawaiian specialties with a fine-dining flair.
- Botanist enthusiasts should book the Garden Tour with Grand Wailea’s head gardener on Thursdays for samples of delicious starfruit and sugarcane grown on the property.
- Elevate your experience with a stay in one of Grand Wailea’s recently renovated Napua guest rooms and suites, each equipped with a concierge, three gourmet dining options daily and a rotating lineup of special experiences in the Napua lounge, including a chef’s station, live entertainment and more.
