Destination Area: Caribbean Ocean/Gulf Of Mexico
Length: 14 NIGHTS
Vessel: Wind Surf


Philipsburg, St. Maarten on November 18, 2017


Philipsburg, St. Maarten (return) on December 2, 2017

$2,499 per person double occupancy, plus port charges.
Book now for $100 on-board credit

For more information call us toll free at 1-877-882-4395.

Explore the Caribbean Leeward Island Chain at a leisurely pace for 14 days.

Wind Surf is the largest ship in our fleet, and among the most luxurious. Suites are twice the size of standard cabins, and all cabins have a ...

Read more about the Wind Surf     

  • Anchor alongside the pristine beaches of Pigeon Island’s 40-acre National Park and explore at your leisure
  • Discover St. Lucia’s UNESCO Site when you see the twin Pitons rising majestically from the turquoise sea
  • Embrace the island life on St. Kitt’s one-of-a-kind Shipwreck Beach
  • Enjoy the unspoiled paradise of Barbuda with its pink beaches and soaring frigate birds
  • Soak in the natural bathing pools of "The Baths" at Virgin Gorda
  • Enjoy Windstar’s exclusive Signature Beach Barbecue at Prickly Pear Beach
  • Swim in the emerald pool below the falls on Dominica
  • Mingle with the glitterati in St. Barts
  • Overnight in Jost Van Dyke and Virgin Gorda for more in-depth exploration

Skip the usual Caribbean cruise stops and discover the small harbors, overlooked havens and most remote secrets among the Leeward Islands. Whether you’re looking for hidden shops, sampling new cuisine or seeking a local place to sip rum cocktails over the melodic beat of steel drums, this highly personalized adventure is an intimate opportunity to familiarize yourself with the lesser-known charms of Barbuda, Soper’s Hole in Tortola, Gustavia in St. Barthémy, St. Lucia’s Pigeon Island and much more.

Philipsburg, St. Maarten
Philipsburg was founded in 1763 by John Philips, a Scottish captain in the Dutch navy, and soon became a bustling center of international trade. Two historic forts bear witness to Philipsburg's strategic importance in St. Martin's history: Fort Amsterdam and Fort Willem.

The main shopping district, Front Street, is in the heart of the city. Philipsburg has a port that is home to many cruise liners and tall ships.

Falmouth Harbour, Antigua
Falmouth Harbour is the home of the Antigua Yacht Club, the host club for yachts sailing in Antigua Race Week and the Antigua Classic Yacht Regatta. It is situated on the south side of Antigua, at the opposite end of the island from St. John's the major cruise ship port on Antigua.

During the race & regatta weeks, Falmouth Harbour is filled with some of the most beautiful classic yachts, and the speediest of racing yachts. The races are held just outside the harbor entrance, ranging up to 8 miles offshore. These races are international events, attracting the best of the big yacht sailors from around the world.

Right next door to Falmouth Harbour is English Harbour, and the famous Nelson's Dockyard, Naval Base for the British Caribbean fleet during the great age of sail, from the late 1700's until it was abandoned in 1889. Nelson's Dockyard has since been restored. You can see the capstans used to warp ships into the sheltered anchorage, the remains of a sail loft, shore batteries for the protection of the ships in harbor, Clarence House built for soon-to-be crowned King William IV when he was captain of H.M.S Pegasus, one of the ships in Horatio Nelson's fleet. Around the harbor you can find Shirley Heights and the colonial observation post for the harbor, now a good vantage point to watch the racing yachts maneuver.

Soper's Hole, Tortola, BVI
Soper's Hole is a favorite "gunkhole" on Tortola, a delightful spot to anchor. Soper's Hole exhibits quaint charm and is a center of activity. Soper's Hole is a very picturesque harbor as well as an excellent overnight anchorage.

Blackbeard, rumor has it, used Soper's Hole as a lookout from which his men could spot ships laden with riches headed for Europe. The only Jolly Roger you'll see today in Soper's Hole is the Jolly Roger Restaurant & Inn.

Tortola is the largest island in the BVI chain. There are a variety of things to do and see such as powdery white sandy beaches, lush green mountains and a yacht filled harbor. Notice that the past of the West Indies meets the present in Tortola.

Europeans began making their mark in Tortola after 1492 when Christopher Columbus spotted the BVI region. In the 16th century the English took over Tortola from the Dutch. Sugar cane was the major income generator and it was African slaves who performed the bulk of the work. The island is primarily focused on the tourist trade and a locus for yachting.

Great Harbor/Jost van Dyke (overnight)
Great Harbor is a fascinating melting pot of British Virgin Islanders & visiting sailors who land on this perfect BVI beach and stay a while! Great Harbor is the center of activity for Jost Van Dyke, one of the most popular anchorages for yachts in the BVI, with a variety of beach bars, including the famous Foxy's.

Virgin Gorda, BVI (overnight)
When you think of Virgin Gorda, you think The Baths - one of the Caribbean's natural wonders, a spectacular formation of gigantic boulders, creating grottoes and caves that you can explore on foot. The island is home for the famous resort of Little Dix Bay, as well as the Bitter End Yacht Club.

Gustavia/St. Barts
There was never any hope of lucrative sugar plantations in St.Barts. It was too dry, too steep, too rocky, and, finally, too small. Unsuitable for agriculture, the island was never coveted as a prize during the colonial wars of the 18th century.

The island did, however, have a serviceable harbor, and this allowed the town that grew around it, Gustavia, to play a key role in that intermittent conflict, a role that was to presage much of its future.

As a free port under Swedish rule, Gustavia provided a trade and supply center for the various warring factions. When a sea captain captured a prize or raided a settlement, he could sell the booty in St. Barths, and at the same time resupply his ship. Overflowing warehouses surrounded a harbor packed with ships from many nations, and a mercantile and architectural tradition was established that has lingered to the present day.

Today, the town has adjusted itself to satisfy the increasing number of visiting tourists. Restaurants, boutiques, and gift shops now line streets once busy with merchants, merchant seamen, and adventurers.

St. Martin / St. Maarten
The smallest island in the world shared by two countries. St. Martin/St. Maarten is big on shopping. You can also try your luck in one of St. Maarten's many casinos. Whether you go Dutch in Philipsburg or prefer Marigot's French touch, you're always welcome.

Barbuda is one of those very few islands in the Caribbean that remains so undeveloped as to seem positively deserted at times. With the exception of the guests of the island's small number of accommodations, the population seems to consist largely of the graceful Fregata magnificens, or frigate bird. As the birds possess a marked preference for the northwest lagoon, Barbuda's seemingly endless white and pink sand beaches are left to the peaceful wanderings of those lucky enough to sojourn here.

Activities on Barbuda are appropriately relaxed, including beachcombing (on the northeastern Atlantic coast), fishing, golf, tennis, snorkeling, diving, or simply soaking up the sun. Points of interest include the Frigate Bird Sanctuary, the truly noteworthy pink and white sand beaches, and an abundance of shipwrecks and beautiful reefs.

Barbuda's history has been intimately tied to that of Antigua for centuries. The first early attempts to settle Barbuda (by both the British and French) were failures, and it wasn't until 1666 that the British established a colony strong enough to survive the ravages of both nature and the Caribs. In 1680, four years before he began cultivating sugar on Antigua, Christopher Codrington was granted (with his brother John) a land lease in Barbuda. With subsequent leases that granted them additional rights to the substantial wreckage along Barbuda's reefs, they became the island's preeminent family. For much of the eighteenth century the Codrington land on Barbuda was used to produce food and to supply additional slave labor for the Codrington sugar plantations on Antigua, and so the Barbuda's fortunes rose and fell with those of its larger neighbor. Testament to the influence of the Codringtons remains today, both in the island's place names and in its architectural remains. On Barbuda's highest point (124 feet) are the ruins of the Codrington estate, Highland House, and on the island's south coast still sits the 56-foot high Martello castle and tower, a fortress that was used both for defense and as a vantage from which to spot valuable shipwrecks on the outlying reefs.

Roseau, Dominica
Dominica is an island republic in the West Indies, specifically in the Windward Islands. The island has 148 miles of coastline, and covers 751 square miles of land area. The population of Dominica is under 75,000. Roseau is the island's capital. Dominica is lush and beautiful, and is home to some of the friendliest people in the West Indies. The island is known as the spot for ecotourists, with many parks and places to mountain climb, nature walk or explore. The diving is great here, too, but the beaches are less attractive than on other islands.

Pigeon Island, St. Lucia
Pigeon Island National Landmark is one of the Caribbean's most historic spots, an important monument of St. Lucia's history. It offers a vivid representation of the cultural and historical monuments of international, civil, military and marine cross currents, characteristic of West Indian history. Pigeon Island offers lots of photo opportunities. You can visit the interpretation center, eat at Jambe de Bois restaurant, walk up to Fort Rodney and view historical ruins. A living museum within a natural setting, Pigeon Island is being nurtured through careful protection and intelligent development to serve the intellectual, cultural, and recreational needs of all who visit this historic site. The picturesque, 44 acre island reserve, grasslands, dry tropical forests, beaches and twin peaks, off the north west end of St. Lucia, was originally surrounded by water but was joined to the mainland by a man made causeway in 1972. The Landmark is perfect for an outing tailored to your specific needs - With or without a guide, the island is an easy and accessible location for relaxing or exploring. Whatever your preference, don't forget your camera for breathtaking photo opportunities.

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