Blending tranquil stretches of white-sand beach with inspiring history, watersports, and spacious villas, few vacation destinations are as attractive for families as the beautiful Caribbean islands.

Whether you’re seeking adventure, relaxation, or both, these three islands, in particular, offer an array of experiences suited for all members of the family, and each is easily accessible with Tradewind’s regularly scheduled shuttle flights and private charters.



Regarded as one of the top sailing destinations in the world, Antigua is known for its ethereal beaches and enchanting historical sites like Nelson’s Dockyard National Park.

Set on four and a half miles of pristine shoreline, Jumby Bay Island welcomes families with an incredible collection of private villas just off the coast of mainland Antigua. And across the main island, Carlisle Bay offers elegant two- and three-bedroom suites and extensive children’s programs framed by verdant rainforest and calm Caribbean seas.

Both resorts serve as jumping-off points for sailing lessons with Ondeck, diving among vibrant coral reefs, and swimming with Southern Stingrays in Stingray City’s interactive eco-tour. On shore, families will find endless opportunities for exploration in natural wonders like Devil’s Bridge and the Pillars of Hercules, the pastel-colored local villages along Fig Tree Drive, and the museum and grounds at Nelson’s Dockyard, which is a beloved UNESCO World Heritage Site.

For family-friendly dining, head to Catherine’s Café to indulge in exceptional French cuisine overlooking Pigeon Beach at sunset.


Photo: Four Seasons Resort Nevis

Photo: Four Seasons Resort Nevis

A serene escape that feels entirely removed from the rest of the world, Nevis captivates families with its secluded shorelines encircling the towering Nevis Peak. Along with beaches and lush rainforest, the island has a distinct element of history with its 17th- and 18th-century sugar plantations – some of which have been restored as luxury hotels.

In the green foothills of Nevis Peak, The Little House at Montpelier Plantation & Beach offers two elegant bedrooms and an abundance of Old World charm throughout its century-old structure, while on the edge of the sea, Four Seasons Nevis features luxurious multi-bed guestrooms and one- to seven-bedroom villas with private pools. (The five-star resort also has the Kids for All Seasons program for children and the option of a fully stocked villa kitchen upon arrival.)

Spend your days visiting historic attractions like Hamilton Estate and snorkeling among the vibrant reefs of Herbert’s Beach. In the late afternoon or evening, stroll Pinney’s Beach to choose from an array of rustic restaurants and sip cool drinks while the kids enjoy the playground at Sunshine’s Beach Bar.

St. Barth

Photo: Antoine Verglas, courtesy of Eden Rock

Photo: Antoine Verglas, courtesy of Eden Rock

Traditionally known as a destination for couples on glamorous escapes, St. Barth is equally suited for families traveling with children. Beaches like Grand Cul de Sac offer calm, shallow waters (with a protective reef circling the bay), and any number of active pursuits from hiking to kite surfing beckon.

Those visiting St. Barth in mid-2018 will find a sumptuous private villa to be the best option, as many of the island’s luxury hotels are still undergoing renovations following last year’s Hurricane Irma. (The island has returned to its quintessential glamour with most restaurants and shops having reopened and annual events going on as planned.) Closer to the holidays, completely restored resorts like Eden Rock, Le Guanahani, Cheval Blanc, Le Toiny, and Le Barthélemy will be open.

The youngest travelers in your group will enjoy sites like the Inter Oceans Museum with more than 9,000 shells from all over the world, while all will delight in snorkeling amongst leatherback sea turtles in Grand Cul de Sac, boating to the iconic Colombier Beach, and indulging in world-class cuisine in Gustavia and beyond. (Try L’Isoletta for thin-crust pizza on the harbor and Sand Bar or Indigo on the Beach for spectacular ocean vistas.)

During your stay, make sure to charter a sailboat for a day to circle the island and watch the brilliant sunset over the Caribbean Sea.