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Yachtsman's Caribbean cruise the world's largest sailing ship with Windstar Cruises

Experience the ultimate Caribbean vacation with Windstar Cruises

There's only one thing better than a Caribbean vacation. And that's a Caribbean vacation on a small ship cruise line. Which is exactly what you'll get with the Yachtsman's Caribbean cruise the world's largest sailing ship with Windstar Cruises.

The aptly named "Wind Surf" is a 350-guest ship designed to whisk you from island to island in comfort. With amenities like complimentary 24-hour room service, non-alcoholic beverages included, welcome cocktails, coffee with the captain on the Open Bridge, a sail away ceremony, and complimentary use of the fitness center and all water sports equipment, you won't have to think about a thing while onboard.

As the official cruise line of the James Beard Foundation, Wind Surf also hosts four restaurants of various upscale cuisine ranging from a romantic grill under the stars to an elegant French bistro. But with no pre-assigned dining times or seats for most dining locations, you're free to eat where and when you please. Because who wants to be told to do anything on vacation?

As if all those amenities weren't enough, Wind Surf is currently undergoing a makeover (to be completed at the end of November) and will soon be sporting an expanded and redesigned spa and lounge area. There's also an addition of the Officer's Suite, which offers guests a chance to stay where the ship's officers have their quarters, providing a unique insider experience you won't find on another cruise line.

Your voyage on Wind Surf begins and ends in St. Maarten. The seven-day adventure will take you to several Caribbean islands, including Anguilla, Antigua, and the British Virgin Islands. Gorgeous beaches, quaint ports reserved for yachtsmen and mouth-watering local eats await you along the voyage. Here are just a few things to explore at each port:

  • Late nights in Jost Van Dyke and Virgin Gorda mean you can enjoy a sunset cocktail from the beach
  • Keep an eye out for celebrities at St. Barts
  • Check out "The Baths" (underground pools) at Virgin Gorda
  • Indulge at Windstar's Signature Beach Party with food and drinks packed with Caribbean flare
  • Discover the hidden Caribbean in Antigua and Anguilla

After a busy day ashore, return to Wind Surf and relax in your stateroom. A fully stocked minibar/fridge, fresh fruit and queen bed with luxurious Egyptian cotton linens await you. Fall asleep to the rocking of the waves and wake up refreshed and ready to once again explore the beauty of the Caribbean.

Ready to book your Yachtsman's Caribbean vacation? Visit Windstar Cruises today.

And to enter for a chance to win a Yachtman's Caribbean cruise for two from Windstar Cruises head to