In a world where the easiest route is usually the most popular, it’s no surprise that many vacationers limit their warm-weather winter getaways to the Caribbean’s more accessible islands—especially if they have kids in tow. And while the quick trip has its advantages, some of the best destinations require more effort.
Add an extra connecting flight to your itinerary to find serene beaches and authentic experiences—without the crowds. Here are four tropical escapes that provide the amenities most valued by travelers—decent accommodations, plenty of restaurants, and reliable medical care in case of an emergency—while also managing to keep mass tourism at bay.
> Virgin Gorda (British Virgin Islands)
Why go: Dubbed the “fat virgin” by a sea-weary Christopher Columbus, the curvy island of Virgin Gorda is one of the BVI’s largest islands and a haven for boaters thanks to numerous picturesque coves and calm seas.
Family-friendly resorts such as high-end Bitter End Yacht Club specialize in sailing courses for both adults and children, but serious sailors can charter boats to fit most budgets via Tortola-based Moorings, one of the region’s most reputable outfitters.
Landlubbers take advantage of beachy attractions like The Baths, a idyllic strip of sand strewn with massive boulders and darkened grottos that children adore, and picture-perfect Devil’s Bay Beach, accessible via a hike from The Baths.
Don’t miss: Island-hopping to nearby Anegada for its exceptional coral reef and to farther-flung Jost Van Dyke for a spot at the famous Soggy Dollar Bar (guests pay with wet money after swimming in from their boats).
Getting there: Most travelers arrive via Tortola, which has regular flights connecting to San Juan and is a 30-minute ferry ride from Virgin Gorda (ferries also run from St. Thomas). Others opt for an air taxi—a tiny inter-island flight—from St. Thomas or San Juan.
> Culebra (Puerto Rico)
Why go: Puerto Rico’s San Juan airport may be the Caribbean’s busiest, but few tourists make their way to Culebra, a small island located approximately 18 miles east of the mainland.
With a population of fewer than 2,000 people and only allowing locally owned inns and rental homes, Culebra has the unspoiled, undiscovered vibe that keeps regulars returning yearly—and guarding their secret spot fiercely.
The island’s beautiful beaches are its main attractions, with Playa Flamenco consistently ranked among the world’s best. It’s also known for its excellent snorkeling sites. If you have younger children, Katya Plyshevsky, an in-the-know mom who visits yearly with her children, recommends hiking to more secluded Playa Carlos Rosario.
Don’t miss: Lunch at Barbara Rosa—owned by a local woman who serves fresh-caught fish, cooked in her own kitchen, on her front porch—and a day trip to Culebrita, a small neighboring cay with a cute lighthouse and great beaches.
Getting there: Local airlines operate frequent half-hour flights between San Juan and Culebra. Those who prefer to avoid small planes can catch a ferry from Fajardo, a 45-minute drive from San Juan airport. The boat ride itself can take up to 1.5 hours, so most choose the plane.
> St. John (U.S. Virgin Islands)
Why go: Skip the busy cruise port of St. Thomas and board a 20-minute ferry to St. John, the smallest and—with 60 percent of the island protected as national parkland—most picturesque of the three major U.S. Virgin Islands (St. Croix being the third).
Green and mountainous, much of St. John is undisturbed forest and mountain, with campsites, uncrowded public beaches, and hiking trails a more common sight than big-name hotels—and not a high-rise in sight.
Downtown Cruz Bay, the island’s main town, is a hub for locals as well as visitors, with plenty of casual eateries serving classic Caribbean fare as well as more global cuisine.
Getting there: Ferries run from Red Hook and Charlotte Amalie in St. Thomas, but the ride is shorter from Red Hook and the boats run more frequently.
> St. Barth’s (French West Indies)
Why go: Avoid around Christmas, but otherwise ignore the celebrity hype. This tiny French island is a mellow European-style escape for the majority of the year, and it’s ideal for families. With only 3,000 residents and careful restrictions on new construction, the island more closely resembles a Cote d’Azur village than it does the Caribbean’s more popular islands.
And, contrary to public opinion, St. Barth’s can also be a bargain. Supermarkets stock freshly baked baguettes, good cheese, and produce plus reasonably priced wines from the motherland, so many families and larger groups rent cottages and cook to avoid expensive restaurants.
The island’s interior is hilly and steep, and most activities revolve around the water, with some of the Caribbean’s best kite surfing, diving, deep-sea fishing, and even surfing found there. Crime is practically nonexistent, too, meaning parents with older children can let them explore on their own without much concern.
Don’t miss: A day at Colombier Beach—accessible only via a hiking path or by boat and with calm waters ideal for first-time or kiddie snorkelers—and fresh morning pastries from La Petite Colombe, the island’s best bakery.
Getting there: Take a puddlehopper from St. Martin (a 15-minute flight) or a longer connection via San Juan (just under an hour). Ferries also run between St. Barth’s port and St. Martin, but waters can be rough on travelers lacking steady sea legs.
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