Flights to/from St. Maarten
Smaller Ship / Smaller Ports
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.
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.
Day 1: Feb 10, 2024
Depart 7:00 PM
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.
Day 2: Feb 11, 2024
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.
Day 3: Feb 12,2024
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.
Day 4: Feb 13, 2024
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.
Feb 13, 2024 7:00pm-
10:00pm Feb 14, 2024
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.
Day 6: Feb 15, 2024
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
Day 7: Feb 16, 2024
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.
Saturday Feb 17, 2024
Let yourself go – at Windstar’s Signature Beach Party, where the Caribbean spirit is in full swing.
Let the Bubbly Pool on Jost Van Dyke wash your cares away.
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.
Stroll Pusser’s Landing, the charming boardwalk of Soper’s Hole on your way to a secluded beach
Find your beautiful spot on the beach while you sample some of the most delicious rum punch found in the Caribbean at Road Bay
This trip has it all, including Valentine's Day! All at savings starting at $1,400!
On any day, our 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 their 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 bowls of flowers and fresh fruit will still be waiting for you, along with rich tufted headboards, soft seascape colors, beautiful new upholstery, and fine count Egyptian cotton linens welcome you to an oasis of relaxing indulgence.
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.
The beauty of Wind Surf's dining offerings is that all restaurants are included within your cruise fare, including the ship's specialty restaurants, Candles and Stella Bistro. For a ship of Wind Surf's size, we found the range of dining options superb at dinnertime.
The ship's open-air Pool Bar is located on the Main Deck below Compass Rose.
Guests can talk with the Captain and officers on watch, view the navigational charts, and enjoy one of the best views on the ship.
The Compass Rose is Wind Surf’s lounge area which includes a small stage for a two person band, dance floor, bar and doors leading to an outside seating area. The venue makes the ideal location for guests to enjoy sailaways and pre-dinner drinks.
Stylish comfort and ocean views welcome you in 188 square feet of beautifully designed comfort. Your queen bed (which can be separated as twins if you prefer) is swathed in luxurious Egyptian cotton linens. Before or after you enjoy an invigorating massage shower with soothing L’Occitane® bath products, wrap up in your waffle-weave robe, have a snack from the fresh fruit bowl, or simply stretch out and smell the flowers.
With 376 square feet, you’ll find the perfect space for time together — and plenty of room for time to yourself. You’ll even enjoy two full separate bathrooms. All the amenities of the staterooms await you, plus a beautiful sitting area, and two flat-screen television sets with DVD players.
You’ll be pampered perfectly with ocean views, white sand beach and amenities galore. Located on St. Maarten just south of the amicable French/Dutch divide, you’ll find adventure, serenity, and your life’s dreams come true at this exotic, tropical island resort.