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Wind Spirit, Leeward & Windward Caribbean Havens ex St Maarten to Bridgetown

14 Night Cruise sailing from St Maarten to Bridgetown aboard Wind Spirit.

Departs
Saturday, 21st February 2026
Ship
Wind Spirit
Windstar Cruises
Pricing is From and Per Person
Cabin Twin Triple Quad Single
N/A N/A N/A N/A

Please note, while prices and inclusions are accurate at time of loading they are subject to change due to changes in cruise line policies and pricing and due to currency fluctuations. Currency surcharges may apply. Please check details of price and inclusions at time of booking.

14 Night Cruise sailing from St Maarten to Bridgetown aboard Wind Spirit.

Highlights of this cruise:

St Maarten
St. Maarten is one of the most rewarding stops for a cruise-ship passenger. The island is divided between French St. Martin in the north and Dutch St. Maarten in the south. Each side manages to retain its own distinct flavor.

The French side (St. Martin), is certainly more relaxed and sophisticated. There are first-class resorts and secluded white sand beaches. Its capital, Marigot, is Mediterranean resort-like, with yachts in the harbor, and open-air markets and shops lining the waterfront. A bit to the north, Grand Case is known for the island's best restaurants.

The Dutch side (Sint Maarten) is a lively destination of white sand beaches, casinos, historical sites, shopping venues and lot of nightlife. Most ships dock in Philipsburg, the capital of Dutch St. Maarten. Its two main streets, Frontstreet and Backstreet, are bustling thoroughfares lined with shops and restaurants.

Jost Van Dyke
The British Virgin Islands, about 60 (mostly uninhabited) islands and cays, are one of the Caribbean's most popular destinations. Jost Van Dyke is a casual island with protected anchorages, fine beaches and beachfront restaurants and bars. It is said to have been named after an early Dutch settler, a former pirate.

At Great Harbour, Little Harbour, and White Bay there are safe, protected anchorages and unspoilt beaches shaded with coconut palms and seagrape trees. Discover inviting restaurants, bars, and small shops selling local treasures.

Parties here are legendary, especially at Foxy's. This bar and its owner are known to travellers from around the world for the New Year's Eve and Halloween parties, when Great Harbour fills up with yachts.

Gustavia
Saint-Barthélemy (St Barts) is a French island located in the Caribbean among the Leeward Islands. It lies near the islands of Saint Martin, Saba and Anguilla off the coast of Puerto Rico. Gustavia is the main town on St Barts, and has long been considered a playground of the rich and famous. It’s known for its beautiful pristine beaches, gourmet dining in chic bistros and high-end designer shopping.

Excellent shopping can be found on Quai de la Republique, Rue du General De Gaulle, and Rue Oscar II. The shopping is within easy walking distance of the tender wharf. The flea market and pastry stores in Gustavia are also a treat for tourists.

Exploring Gustavia you’ll find the St. Barths museum which is small, but somewhat interesting and the fort at the northern end of the harbor ( Fort Gustav III) offers great views of the harbor for photo opportunities. Shell Beach is popular for families with kids as it has little surf, and lots of tide pools.

Cruise Itinerary
Date Activity Arrive Depart
21/02/26 St Maarten 7:00 PM
22/02/26 Sopers Hole, British Virgin Islands 8:00 AM 6:00 PM
22/02/26 Jost Van Dyke, British Virgin Islands 7:00 PM overnight
23/02/26 Jost Van Dyke, British Virgin Islands 10:00 PM
24/02/26 Virgin Gorda, British Virgin Islands 7:00 AM 5:00 PM
25/02/26 Gustavia, St Barts 8:00 AM 10:00 PM
26/02/26 Road Bay, Anguilla 8:00 AM 6:00 PM
27/02/26 Falmouth, Antigua & Barbuda 8:00 AM 5:00 PM
28/02/26 St Maarten 6:00 AM
01/03/26 Basseterre, St Kitts & Nevis 8:00 AM 9:00 PM
02/03/26 Gustavia, St Barts 8:00 AM 10:00 PM
03/03/26 Montserrat 11:00 AM 10:00 PM
04/03/26 Les Saintes, Guadeloupe 8:00 AM 5:00 PM
05/03/26 Roseau, Dominica 8:00 AM 5:00 PM
06/03/26 Pigeon Island, St Lucia 7:00 AM 4:00 PM
07/03/26 Bridgetown, Barbados 6:00 AM
Itinerary may vary by sailing date and itineraries may be changed at the cruise lines discretion. Please check itinerary details at time of booking and before booking other travel services such as airline tickets.

Available Sailing Dates