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It's Multiple Choice

Town & Country US

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October 2025

Why pick just one island to visit? Sleek, yachtlike cruise ships can take you in style to many.

- BY SUE BRYANT

It's Multiple Choice

Star Clipper is modeled on the graceful clipper ships of the 19th century. They're what inspired young men to go to sea.

All are smaller than typical cruise ships—no casinos, shops, Broadway-style shows, or packed schedules of activities. All are nimble—able to anchor where larger vessels cannot. Some have water sports marinas, so you can slip right into the sea. Choose one of the masted ones and there’s also the romance of travel powered by the wind. We especially like the ships below—and their unique itineraries. To fully live the yachting life, tie two or more trips together. Now, that’s “wintering in the Caribbean.”

LE PONANT Ponant's three-mast, 16-cabin sailing yacht. ITINERARY Seven days, Guadeloupe to St. Martin. HIGHLIGHTS The Iles des Saintes: fishing boats in pretty bays, French Creole houses, seaside cafés. Antigua’s scenic Falmouth Bay and restored Georgian-era Nelson's Dockyard, from which Britain ruled its Caribbean empire. St. Bart's: Le Ponant will fit right in with the gin palaces in Gustavia Harbor. And Anguilla's beachy, decidedly not sceney Prickly Pear Cays. VIBE Interiors are a smart new cream and navy, there's a marina, and every meal at Le Diamant is an occasion: This is the only Relais & Châteaux sailing ship. DATES Jan. 10-17.

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