Day 1 Philipsburg, St Martin
It's been some 300 years since the Dutch and French established a truce on tiny St. Martin (St Maarten), dividing the island into two delightfully distinct yet amicable parts. So amicable, in fact, that you can cross back and forth freely from one side to the other. Philipsburg is the vivacious capital of the Dutch half. Along Front Street, the citrus-colored buildings are home to gourmet restaurants, lively casinos and some of the best duty-free shopping in the world. Pause for a taste of the local guavaberry rum, listen to street musicians play on the broad boardwalk or head to the French-side village of Grand Case for conch fritters and quaint Creole architecture. Board your small ship, the Wind Spirit, and settle in for your upcoming Caribbean adventure.
Day 2-3 Falmouth, Antigua
Your first port of call on your Caribbean tour is Antigua. It's said that Antigua has 365 beaches—one for every day of the year. But this precocious former British colony also boasts a fascinating maritime history. We'll head for Falmouth Harbour in the south, across the island from the large cruise ship port of St. John's and much closer to the island's most famous attraction, Nelson's Dockyard. Admiral Lord Horatio Nelson spent the early days of his career here helping to protect England's sea trade. Today, it's the only working Georgian dockyard left in the world, and well worth a stroll through the museum and gracious 18th-century buildings that now house inns and shops. Along with beaches and history, Antigua's bounty includes a verdant rainforest, stately old sugar plantations and mills, and tempting English traditions such as afternoon tea.
Day 4 Sopers Hole, Tortola, BVI
Unlike many islands in the Caribbean, Tortola has kept growth in check, with no buildings taller than a palm tree and no fast food restaurants. Yet its natural attractions—including white sand beaches, a primeval rainforest, and water so clear it gives you vertigo—have turned this into a mecca for yachtsmen, snorkelers, and divers. Moor at Soper's Hole, much less crowded than Road Town where the big ships dock. Pirate history abounds here. Soper's Hole was the one-time hangout of Blackbeard the pirate, and nearby Norman Island is said to be the inspiration for Robert Louis Stevenson's novel, Treasure Island. It's rumored that treasure still lies there waiting to be discovered. When it's time to depart, sail away at sunset through Sir Francis Drake Channel, once known as "Freebooter Gangway."
Day 5 Jost Van Dyke, BVI
Ask any yachtsman about Jost Van Dyke and watch his face light up. Known as the "Barefoot Island" for its laid-back lifestyle, Jost (rhymes with "toast") has a reputation that belies its tiny size. Covering just eight square miles and with fewer than 300 residents, The island only got electricity in 1995, yet it's world-famous for its parties on Halloween and New Year's Eve. Guests on larger cruise ships must ferry over from Road Town, but you'll anchor right in Great Harbour, the "commercial hub." Sip a Painkiller and dine on a flying fish sandwich at the Soggy Dollar, or visit Foxy's for some Calypso and barbecue. Head to the Bubbly Pool for a naturally effervescent soak. Go diving and hand-feed groupers. Come back aboard and count an infinite number of stars.
Day 6 Virgin Gorda, BVI
Virgin Gorda is where you'll find the most exclusive resorts in the British Virgin Islands, lured by its other-worldly beauty. With a draft of only 17 feet, Wind Surf gives you rare access, maneuvering through the gap in the reef to North Sound—a secluded part of Virgin Gorda usually reserved for much smaller yachts. Anchor just off Vixen Point on gorgeous Prickly Pear Island, a BVI National Park. Take a tender ashore and hike to North Beach, where turtles often nest. Venture south to The Baths, a labyrinth of Rubenesque granite boulders surrounding beautiful white sand beaches and turquoise grottoes. Or further north to mysterious Anagada Island, a flat limestone atoll boasting miles of white sandy beaches, the third largest barrier reef in the world, and hundreds of pink flamingos.
Day 7 Gustavia, St Barthelemy
When the rich and famous head to the Caribbean, like as not they head to St. Barts. Not a bad outcome for an island the French originally sold off as being too hilly, rocky, small, and dry to be profitable. Others did see potential here though—first French buccaneers and later Sweden, which turned it into a profitable free port during the colonial wars of the 18th century. France eventually bought the island back, but the free port status remains, making this a great place to shop for everything from the latest French fashions to island crafts. Have lunch at the infamous "Cheeseburger in Paradise" made famous by Jimmy Buffet. Watch for celebrities along the Rue de la République. Stand at the rail as you depart under the stars by sail power alone, without even starting the engines.
Day 8 Philipsburg, St Martin
Return to St Martin this morning and disembark after breakfast.