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The Art of Island Hopping

There’s no better way to explore the Caribbean’s white sand beaches and turquoise waters than hopping from idyllic island to idyllic island.

If you had to choose just two destinations to explore, St. Barts and Virgin Gorda both deliver that rare combination of next-level luxury and pristine natural beauty. A 50-minute charter flight or a scenic sail ferries Members between the islands.

A bit wild, a bit wonderful, St. Barts is the place to see-and-be-seen
One of the most well-known islands, Virgin Gorda boasts an awe-inspiring geological wonder

St. Barts, an isle in the French West Indies, is synonymous with luxury and known for its see-and-be-seen celebrity crowd. But it also has a wild side, like Colombier Beach. Set on the island’s northwest tip and accessible only by a short hike or catamaran, this secluded patch of sand is home to a resident herd of goats and is also a dreamy spot for a picnic of gourmet sandwiches (don’t miss the prosciutto, goat cheese, arugula, and pesto on a ciabatta roll) from Maya’s to Go. Colombier is one of 14 stunning beaches. Lorient is a favorite with surfers, while Grand Cul-de-Sac has a shallow, reef-protected bay perfect for water sports.

The Club’s island-chic villas are tucked away on a hillside with dramatic sea views but are within minutes of the beach. A private chef can prepare an al fresco seafood feast by your infinity pool, or you can hit the town and discover St. Bart’s impressive dining scene. Your concierge can score hard-to-get reservations at top tables like Orega, a French-Japanese fusion spot with fantastic sushi, or Sand Bar, a restaurant helmed by star chef Jean-Georges Vongerichten set within the glamorous Eden Rock hotel.

Virgin Gorda, part of the British Virgin Islands, flies a bit more under the radar, but after his visit, Member Jim Reilly deemed it one of the top three destinations in the Club’s portfolio. The vibe is more low-key with quiet coves and tucked-away beach bars that feel like insider secrets. You can even find yourself standing knee-deep in cerulean water at the island’s most iconic natural feature, The Baths. This geological phenomenon dates back millions of years and the towering rocks and boulders form magical natural pools that are a must to explore.

The island’s spectacular nature captured the attention of Laurance Rockefeller when he was sailing through the Caribbean in 1958. He happened upon a half-mile of untouched beach on Virgin Gorda, bought it, and in 1964 opened a resort that is now Rosewood Little Dix Bay. The epitome of barefoot luxury, the resort and its endless amenities (an open-air rum bar, a Sense Spa, two pools) are just a short golf cart ride from the Club’s six residences. Each four-bedroom villa has its own private pool and balconies with sweeping ocean views. “We felt like we had our own slice of paradise all to ourselves,” says Member Kevin McManus of his villa. “Being able to sit by the pool and have a cocktail and just enjoy the incredible view of Little Dix Bay was so special. We’re already trying to go back.”