Stars of the Greater Antilles
From $4,463 per person
12 days
Ship: Wind Surf
From $4,463 per person
12 days
Ship: Wind Surf
Day-by-day description of your cruise and cruise activities.
Cozumel
The Mesamerican Barrier Reef spans 14 miles around the Mexican island of Cozumel and the impressive marine diversity here makes it an excellent place for snorkeling and diving. Chankanaab, an eco-park surrounding a lagoon offers underwater caverns that are home to dolphins, manatees and sea turtles. Or take a ferry ride over to the mainland to explore the beaches of Playa del Carmen.
Grand Cayman
The largest of the Cayman Islands, Grand Cayman is known for its beautiful beaches and coral reefs. Seven Mile Beach, for one is a long stretch of white sand, calm turquoise waters and shops and restaurants. Stingray City is the most popular attraction where the stingrays can be touched, fed and even held. The island has one cross-country walking path, the Mastic Trail and horseback riding on the beach may be the best way to experience the beauty of this place.
Cayman Brac
On tiny Cayman Brac, The Bluff, a limestone cliff running the length of the island contains numerous caves including the Bat Cave. It is a nature lover’s dream of lovely secluded beaches and lush green forests. Birdwatchers can search for endangered parrots, brown boobies and peregrine falcons or see the parrots at the Parrot Reserve. The hiking trails that crisscross the island lead to historic sites, reptilian habitats and unusual flora.
Ocho Rios, Jamaica
Tourist friendly Ocho Rios is situated in what the locals refer to as “the garden parish” with its abundance of greenery and scenery. See the popular Dunn’s River Falls or zipline at Mystic Mountain Rainforest. Visit National Heritage Sites like the Port Maria Courthouse or Fort Haldane. See the estate made famous in the James Bond “Goldeneye” movie and weave through the variety of shops at the Ocho Rios Craft Market.
Santo Domingo
La Capital, as Santo Domingo is affectionately known, is a UNESCO site and one of the oldest cities in the Caribbean, with Zona Colonial buildings dating back to the 1500s. Santo Domingo is also considered the most modern metropolis in the Caribbean doing a great job of converging old and new. At the heart of the Zona Colonial, a pedestrian-friendly maze of cobblestones and interesting architecture is the first cathedral built in the New World. Find time to sample the aromatic coffee and cacao.
La Romana
La Romana has something for every outdoor lover. White-sand beaches, pristine coral reefs, shallow and extreme depth waters teeming with marine life, fields of sugar cane, and cave-riddled forests where Taino rock art and fresh-water springs can be found. It is also home to the renowned Casa de Campo Resort with its award-winning golf course and 16<sup>th</sup> century Altos de Chavon, an amazing replica of a Mediterranean village.
Jost Van Dyke, Great Harbour
For an island comprised of a mere eight square miles, it’s amazing how much there is to do on Jost Van Dyke. Visit the national park on nearby Diamond Cay, snorkel among swaying sponges and angelfish at Sandy Spit, or pilot your own boat around Sir Francis Drake Waterway. After all that, you’ll be ready for an evening drink on the beach — where you can admire your Windstar ship aglow in the harbor.
Virgin Gorda / Prickly Pear, British Virgin Islands
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<li><strong>The beautiful Bank Barrier coral reef wavers just beneath you as your ship makes the break to the bird sanctuary of Prickly Pear Island, so named because it is dotted with prickly pear cacti. Although uninhabited, it does have a beach bar and water sports facilities. Not far away lies the curious assembly of house-sized boulders called “The Baths,” which form huge underground pools and caverns.</strong></li>
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<strong>Please note: only guests with shore excursions booked through Windstar can be tendered to Gun Creek.</strong>
Philipsburg, St. Maarten
Pastel-colored buildings and shops filled with tempting souvenirs herald your arrival to bustling Philipsburg. Situated near the harbor on the Dutch side of St. Maarten, Philipsburg owes its discovery to Christopher Columbus in 1493. Today, celebrated Front Street is home to a number of local Creole restaurants as well as jewelry stores, stylish boutiques, and lively casinos for visitors seeking an upbeat island experience.
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Wind Surf is the crown jewel of Windstar’s fleet—a majestic five-masted sailing yacht that delivers the romance of classic seafaring paired with the elegance and comfort of a modern small ship. As the largest vessel in Windstar’s collection, Wind Surf carries just 342 guests, preserving the line’s commitment to intimacy while offering generous space, upscale amenities, and a truly immersive style of travel.
Originally built in 1990 and acquired by Windstar in 1998, Wind Surf has undergone a series of thoughtful refurbishments that honor her graceful nautical lines while updating the interiors and onboard offerings to reflect a contemporary, boutique-luxury standard. Her soaring sails—automated yet fully functional—allow guests to experience the beauty of wind-powered cruising, often sailing into port with a sense of drama and authenticity no larger ship can replicate.
The ship features 154 ocean-view accommodations, including 31 suites and two deluxe Bridge Suites. Each stateroom is designed with timeless materials and a calm, coastal-inspired aesthetic. Marble bathrooms, L’Occitane amenities, premium linens, and well-appointed sitting areas provide comfort and functionality, while the larger suites offer expanded living space and additional privileges, including preferred dining reservations and personalized service.
Dining aboard Wind Surf is a sophisticated yet unpretentious affair, with multiple restaurants that celebrate culinary variety and regional inspiration. Amphora, the main dining venue, offers a nightly menu of gourmet dishes in an elegant, open-seating setting. Stella Bistro showcases refined French cuisine with modern flair, while Candles transforms the deck into a romantic, open-air grill under the stars. The Veranda is a casual breakfast and lunch spot overlooking the sea, and the Yacht Club Café offers light bites, specialty coffees, and ocean views throughout the day.
The onboard experience is as much about rejuvenation as it is exploration. Guests can unwind in the full-service World Spa by Windstar, exercise in the fitness center, or enjoy a swim in the pool followed by a soak in one of several hot tubs. A signature feature of the yacht is its watersports platform, which opens directly onto the sea and provides complimentary access to paddle boards, kayaks, snorkel gear, and more when anchored in select locations.
Wind Surf sails to some of the world’s most enchanting coastal regions, including the Mediterranean, the Caribbean, and Northern Europe. Her size allows her to slip into smaller ports and scenic harbors inaccessible to larger cruise ships, enabling more meaningful encounters with local culture, history, and natural beauty.
Elegant yet relaxed, polished but never pretentious, Wind Surf is designed for travelers who appreciate the thrill of the open sail, the comfort of spacious suites, and the rewards of authentic, unhurried discovery. She is not just a ship, but a sailing experience reimagined for the modern world.
Reach out to our travel concierges today to create your perfect journey.
