Bask on remote beaches resplendent in natural beauty during this relaxing, unrushed, and uncrowded 7-day getaway to secluded Caribbean destinations Windstar specializes in. Board a private speedboat bound for Little Bay, Anguilla’s smallest and most private beach, then snorkel among flitting grunts, wrasses and snappers. Guide your own rigid inflatable boat (RIB) through Sir Francis Drake Waterway bays and isles around Jost Van Dyke. Sink in solitude to the silent depths where an 1867 steamship rests, an iconic Tortola dive site that doubled as an underwater movie set. Embark from Windstar’s onboard Watersports Platform on your own self-directed snorkeling and kayaking adventures. Find the warm sunset twilight during an overnight port stay at Virgin Gorda. Windstar takes you to the secret beaches and invites you to join us for our private Signature Beach Party, a fun in the sun affair, full of the rhythm and joy of the Caribbean.
- Let yourself go – at Windstar’s Signature Beach Party, where the Caribbean spirit is in full swing.
- Relax on the sands of Norman Island, inspiration for Robert Louis Stevenson’s Treasure Island
- Soak in the natural bathing pools of "The Baths" at Virgin Gorda.
There are no future departures for this trip at this stage.
Arrive on board.
Arrive at the boardwalk of Pusser’s Landing and mingle with other yachtsmen in the utterly charming marina at Soper’s Hole. Find a deserted stretch of beach to kick back and ponder this tiny port’s rich heritage of romance, pirates, and adventure. An evening departure features a once-in-a-lifetime romantic sunset Sail Away.
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 harbour.
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. Althought 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.
Affectionately known as St. Barts, the Caribbean’s most chic island adds a French flair to Riviera-like beaches and duty-free boutiques. Walk past gingerbread cottages in search of celebrities, shop for designer fashions, or sip the island’s signature ti punch as kite surfers fly by.
With its protected shoreline, calm surf, spectacular coral reefs and sugar-soft beaches, Road Bay has become a destination for boaters, with its delightful restaurants, bars, and shops. Anguilla has some of the most beautiful sunsets and delicious rum punch to be found in the Caribbean. It is also home to Cuban tree frogs, red-footed tortoise, green iguanas and five species of bats. Worth checking out is Wallblake House, a heritage plantation house and museum said to be the oldest building on the island and located nearby.
It’s said that Antigua has 365 beaches – one for every day of the year. See how many you can discover as our stay in port stretches into the evening to accommodate them all. Watch the stars come out as darkness falls and imagine how residents of Andromeda must envy you.
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. Today is the day to disembark.
Itineraries are subject to change.
Wind Surf

Crew: | 210 |
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Length | 535 feet |
On any day, the 342-guest flagship, Wind Surf, the world’s largest sailing ship, draws admiring glances as she glides majestically into port with her tall sails billowing. And her beauty is far more than skin deep. During any cruise, you will find the perfect setting for ‘making an entrance’ in the beautiful reception area – and, appropriately, that’s only the beginning.
When you return to your stateroom, the luxury gets personal. Windstar’s signature bowl of fresh fruit will still be waiting for you, along with rich tufted headboards, soft seascape colours, beautiful new upholstery, and fine count Egyptian cotton linens welcome you to an oasis of relaxing indulgence.
D I N I N G
Fine dining has always been a pillar of the Windstar experience. As the Official Cruise Line of the James Beard Foundation featuring locally inspired cuisine, developed by a list of culinary all-stars using new flavors and fresh ingredients.
Amphora: Amphora presents a contemporary, international menu and fresh local dishes. The room features mirror panels with Murano glass, soft lighting, wall coverings, and art work. Dishes by James Beard Foundation affiliated chefs are served nightly.
Candles: A romantic setting offers alfresco dining with fine steaks and grilled skewers on the menu, where guests can dine under the stars. Reservations required once on board.
Stella Bistro: Features French-inspired cuisine, exclusively onboard Wind Surf. Reservations required once on board.
Veranda: An inviting breakfast and lunch buffet with outdoor seating offers a variety of options including many local ingredients.
Yacht Club Café: A pleasant lounge and all-day snack bar, which is the theperfect place to relax with new friends.
Complimentary in-room: 24-hour room service menu for in-room dining features coursed menu from the main Amphora dining room during dining hours.
P U B L I C S PA C E S
Public Areas: Entertainment lounge, Compass Rose Bar, Star Bar, Terrace Bar, pool, fitness center, WorldSpa by Windstar, two whirlpools, Yacht Club Cafe, Star Boutique.
Watersports Platform: Swim directly from the yacht’s platform and enjoy complimentary snorkeling gear, paddleboards, kayaks and floatable water mats. World Spa by Windstar: Full-service salon and spa from around the world. Offerings include massages, body treatments, facials, manicures, pedicures, aromatherapy, acupuncture.
O P E N B R I D G E
Guests can talk with the Captain and officers on watch, view the navigational charts with the crew and enjoy one of the best views on the ship.
C O M M U N I C AT I O N & E L E C T R O N I C S
Computers, wireless Internet, and cell phone service. Each stateroom/suite is equipped with one standard U.S. 110 and European 220 volt (converter recommended) electric outlet.
S E R V I C E S
Spa services, fitness services, vow renewal, luggage shipping, medical center with full-time physician, wifi, laundry service and onboard cruise consultant.
Wind Surf underwent a significant renovation of public spaces and suites, including an expanded lounge with new lights and sound for upcoming stage performances. Relax into the destinations you’re visiting at the new World Spa by Windstar, which will offer regional spa treatments, including massage styles like Swedish, Japanese Shiatsu and Hawaiian Lomi Lomi. An Officer’s Suite, which might be the only one of its kind, provides you with the chance to stay in the heart of the officer quarters tucked right behind the Bridge.
Everything about Wind Surf speaks of welcome. Come aboard and see it for yourself.
All accommodation features
- Queen Size Bed with Luxurious Linens
- Waffle Weave Robe and Slippers
- TV with DVD Player
- Fully Stocked Mini Bar/Refrigerator
- SafeL'Occitane Bath Amenities
- Fresh Fruit
- Hair Dryers and 110/220 outlets
- Wi-Fi (internet cards can be purchased at reception)
- Bathroom with granite countertop and shower
- Granite vanity with magnifying mirror
