t Sentry box at Fort Christiansted
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Meet your charter yacht on St. Thomas, a busy cruise-ship destination. Here you can explore Fort Christian and downtown Charlotte Amalie before hoisting sail for the short run to uninhabited Great St. James for some fine snorkeling in Christmas Cove.
The Virgins are the most sheltered of the Leeward Islands – perfect for getting a feel for the wind and your vessel as you run east for beautiful St. John. Two-thirds of the island is protected as pristine national park. Step ashore at Cruz Bay to enjoy hiking on the Salt Pond Trail or the Annaberg Plantation Path. Less active travelers can rent a scooter to circumnavigate this hilly isle, or sail to one of the coves tucked along the north shore. End your day with dinner at The Terrace Restaurant in Cruz Bay.
Set sail for the British Virgin Islands. Make White Bay, on Jost Van Dyke island, your first stop for lunch and revelry at the Soggy Dollar Bar – a favorite of yachters from around the globe. And you can’t say you’ve visited the Virgin Islands without dropping anchor in Great Harbour Bay for a “Painkiller” at Foxy’s Bar.
This morning make the short run to Cane Garden Bay and the most tantalizing beach on Tortola island. Head downwind to Smuggler’s Cove, stopping to snorkel, before sailing east along Tortola’s southern coast to Road Town, abuzz with activity. Head inland to enjoy the serenity of hiking in Sage Mountain National Park. Dine ashore at Pusser’s, on the waterfront in Road Town.
Head south to uninhabited Norman Island to snorkel in The Caves – three sea caves at the base of cliffs. Now turn east for RMS Rhone Marine Park. You can snorkel above the wreck; or pre-arrange a scuba dive of the steam ship. End your afternoon in the Spanish Town on Virgin Gorda, and dine with your toes in the sand at Coco Maya.
This morning venture the short distance to The Baths to spend a couple of hours snorkeling amid natural seawater pools and fantastical granite boulders. Then sail up Virgin Gorda Sound for lunch at the Bitter End Yacht Club. Spend the afternoon threading through the Prickly Pear cays then head north for Anegada, a huge coral with blinding white beaches. Anchor off Pomato Point and enjoy a delicious seafood dinner.
A 93 mile (150 km) gap of open ocean separates the easternmost Virgin Islands from Anguilla, so you’ll spend most of the day at the helm. An early morning start should put you in sheltered Road Bay, Anguilla, before sundown. For dinner, head ashore to Blanchards Beach Shack, a taxi ride away at Mead’s Bay.
You’ll want a rest day ashore after yesterday’s crossing. Explore laid-back Anguilla by car, scooter, or local taxi. Don’t miss Wallblake House, Cheddie’s Carving Studio, and the Heritage Collection Museum. Ride over to CuisinArt Golf Resort & Spa for lunch and a round of golf or spa treatments. In the evening, enjoy a memorable dinner at Veya Restaurant (North Hill Village 2640).
This morning head south on a 3-hour sail to Marigot on St. Martin, with time for shopping in the Creole market and lunch at Mario’s Bistro sidewalk cafe. In the early afternoon, head along the northern shore to Île Tintamarre for fabulous snorkeling in St. Martin Marine Reserve. Sail south for Philipsburg, arriving in time for some duty-free shopping in the capital of the Dutch side of this dual-nationality island. Dine at Chesterfield’s before trying your hand at one of Philipsburg’s casinos.
Sail down to alluringly green and mountainous St. Barthelemy, the chic celebrity isle. First, sail your yacht up to the snug and protected wharf in Gustavia, with its fine restaurants, French boutiques, and chic bars. Lunch at La Crêperie before sailing the 3 miles (5 km) to Anse de Colombier, at the northern tip of the island. While here, snorkel and take a short hike ashore for sweeping views. In late afternoon, return to Gustavia for shopping, plus a divine dinner then cocktails at Bonito.
Set sail at dawn for the 60 mile (97km) southwest passage to St. Kitts. Arriving in early afternoon, lunch at El Fredo’s, then walk to Basseterre. There will be time to rent a Moke (a beach buggy) to explore the rest of the island: don’t miss Romney Manor Plantation, the Arawak Carvings near Old Road, and Brimstone Hill Fortress. Dine at Serendipity.
Head north this morning for the volcanic and mountainous tiny isle of St. Eustatius, just 8 miles (14 km) northwest of St. Kitts. Expect a spectacular reach in the easterly trades. Anchor in Oranje Bay and go ashore in Oranjestad for lunch and well-earned cocktails at The Old Gin House. Hike The Quill in the afternoon – a great appetite-builder for a West Indian dinner at the oceanfront Golden Era Hotel.
Your journey 120 miles (195 km) northwest to St Croix will take all day, so set out at dawn to arrive at the island by early evening. Anchor off Christiansted and have a well-earned meal at The Buccaneer Hotel, set in a former sugar mill.
Spend the morning roaming Chistiansted, with its well-preserved 18th-century buildings within easy walking distance of the waterfront, including Fort Christiansvaern and the old Danish Customs House. After an early lunch, set sail to St. Thomas to end your sailing adventure.
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t Sentry box at Fort Christiansted