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Classic Caribbean
Jan 23, 2028 — Jan 30, 2028
Starting from
Early Booking Offer All-In Package
Early Booking Offer SBC
PHILIPSBURG, ST. MAARTEN → PHILIPSBURG, ST. MAARTEN
7 Nights on Wind Surf
From the stunning drama of the Pitons to the captivating charm of Les Saintes; hidden coves and secret beaches to exotic markets and lively cafés, you’ll discover the best of this region with one single Caribbean voyage. Sandy beaches, turquoise waters, lush mountains, and beautiful waterfalls blend with the music, tastes, and joie de vivre unique to the Caribbean life.
Popular Highlights
Discover St. Lucia’s UNESCO site when you see the twin Pitons rising majestically from the turquoise sea.
Savor the distinctive French charm of enchanting Les Saintes.
Embrace the island life on St. Kitt’s one-of-a-kind Shipwreck Beach.
Indulge yourself at Windstar's Signature Beach Party with plenty of Caribbean flavors and spirit to savor and share.
Enjoy the unspoiled paradise of Pinney’s Beach where Nevis volunteers tag sea turtles at night.
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.
This capital of Nevis with its narrow streets and brightly painted Victorian and Georgian stone buildings is full of colonial history. Alexander Hamilton lived here as a child and you can see the ruins of the Hamilton Estate. Lovely Pinney's Beach is nearby and a group of volunteers work at night tagging sea turtles here and on the other beautiful beaches. Walk the main street and check out the Museum of Nevis History, St. Thomas Lowland Church and the Nevisian Heritage Village to name a few of the historic sites here.
Get ready for a full day with plenty to do. Snorkel alongside brilliant parrot fish in the bubbly waters of Champagne Beach. Take a break to enjoy more than 150 species of plants and brilliant red-necked Jaco parrots at the botanical gardens. If you're up for an optional hike, don't miss Boiling Lake and the Valley of Desolation at Dominica's Morne Trois Pitons National Park, a UNESCO World Heritage Site.
With fewer than 300 inhabitants and miles of secluded beaches, it's easy to feel as if you're on your own private island. Saline Bay is a delightful anchorage that separates the Caribbean from the Atlantic - and a perfect place to play with some of the toys from the Watersports Platform.
This is the Caribbean as you've always imagined it, with yacht-filled harbors set against volcanic mountains and endless stretches of palm-fringed beach. The underwater world here attracted the likes of Jacques Cousteau, but even novice snorkelers will enjoy exploring these impossibly blue waters.
With Georgian architecture situated against an irresistible backdrop of emerald green hills, Basseterre is one of the loveliest of the Caribbean's small capitals. Beyond town, more than a quarter of St. Kitts has been set aside as Brimstone Hill Fortress national Park, a UNESCO World Heritage Site.
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.
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Available Dates
| Date | Yacht | Starting from | Actions |
|---|---|---|---|
| Nov 28 (Sun) – Dec 5 (Sun), 2027November 28 (Sun) – December 5 (Sun), 2027 | Wind Surf | ||
| Dec 12 (Sun) – Dec 19 (Sun), 2027December 12 (Sun) – December 19 (Sun), 2027 | Wind Surf | ||
| Dec 27 (Mon) – Jan 3 (Mon), 2028December 27 (Mon) – January 3 (Mon), 2028 | Wind Surf | ||
| Jan 9 (Sun) – Jan 16 (Sun), 2028January 9 (Sun) – January 16 (Sun), 2028 | Wind Surf | ||
| Feb 6 (Sun) – Feb 13 (Sun), 2028February 6 (Sun) – February 13 (Sun), 2028 | Wind Surf | ||
| Feb 20 (Sun) – Feb 27 (Sun), 2028February 20 (Sun) – February 27 (Sun), 2028 | Wind Surf | ||
| Mar 5 (Sun) – Mar 12 (Sun), 2028March 5 (Sun) – March 12 (Sun), 2028 | Wind Surf |