Treasures of the Caribbean and the Windward Islands

Program Overview

Experience seafaring in its most timeless form on this custom-designed, seven-night cruise of the Caribbean’s tropical Windward Islands aboard the exclusively chartered Wind Star. This Five-Star, four-masted small sailing ship features ocean-view accommodations and complimentary Wi-Fi access (conditions permitting). Sail into secluded harbors inaccessible to larger vessels, exploring the Windward Islands’ natural, cultural and historical treasures. Visit Grenada, the “Spice Island,” replete with historical landmarks and rare herbs; Martinique’s rum distillery and Balata Gardens; St. Lucia’s majestic waterfall and volcanic Sulphur Springs; and St. Vincent and the Grenadines, including Tobago Cays Marine Park. Barbados Pre-Program Option is offered.

Program Details

February 26 to March 5, 2022 (Wind Star)
From $3995 plus air View Terms & Conditions
  • Exclusively chartered cruise aboard the Five‑Star small sailing ship Wind Star.
  • Five-Star, ocean-view accommodations.
  • All meals included aboard ship.
  • Complimentary alcoholic and nonalcoholic beverages available throughout the cruise.
  • Complimentary Wi-Fi access (conditions permitting).
  • Specially designed itinerary to the southern Caribbean’s seldom-visited Windward Islands, inaccessible to larger vessels—all excursions included.
  • Sail round-trip UNESCO World Heritage-designated Bridgetown, Barbados, calling at beautiful St. Vincent and the Grenadines, Martinique—“island of flowers”—and St. Lucia, iconic for its Gros and Petit Pitons.
  • Complimentary snorkeling equipment and opportunities to experience the coral reefs of Tobago Cays Marine Park.
  • Excursions to a variety of lush and intriguing ecosystems—including St. Lucia’s Diamond Falls Botanical Gardens.

Day 1 - Depart the U.S. or Canada/Arrive Bridgetown, Barbados/Embark Wind Star

Day 2 - Rodney Bay, St. Lucia/Soufrière

Day 3 - Terre-de-Haut, Îles des Saintes

Day 4 - Fort-de-France, Martinique

Day 5 - Kingstown, St. Vincent and the Grenadines/Admiralty Bay, Port Elizabeth, Bequia

Day 6 - St. George’s, Grenada

Day 7 - St. Vincent and the Grenadines/Tobago Cays

Day 8 - Bridgetown, Barbados/Disembark ship/Return to the U.S. or Canada

View detailed program itinerary >

Wind Star

Five-Star Sailing Yacht

Rated among the top cruise ships by Condé Nast Traveler, the intimate, four-masted Wind Star offer unforgettable Five‑Star sailing experiences. A harmonious alliance of nautical history and elegant style, designed to sail from deep seas into shallow lagoons inaccessible to larger vessels, making each feel like your own private yacht.

Learn more about the Wind Star >

The Beauty of Barbados Pre-Program Option

The ideal complement to your cruise, historical Barbados celebrates a thriving geographical and cultural landscape. Celebrated Bridgetown showcases a fascinating fusion of more than 350 years of English and Afro-Caribbean architecture, culture and traditions. Enjoy a walking tour of Bridgetown’s UNESCO-designated historic center. Visit the Carenage, the focal point of the city, and the site of the iconic Chamberlain Bridge. Tour the notable George Washington House, where the first president of the United States stayed for two months as a young man. In extraordinary Hunte’s Gardens, tropical plant life blooms in a beautifully landscaped rainforest gully. Visit St. John’s Parish Church, one of the oldest churches in Barbados, dating from 1645. Accommodations are for two nights in the deluxe Hilton Barbados hotel.

The Pre-Program Option is available at additional cost. Details will be provided with your reservation confirmation.

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Program Itinerary

Day 1 U.S. / Bridgetown, Barbados

Depart the U.S. for Barbados. Upon arrival, embark Wind Star. Join your traveling companions for the Captain’s Welcome Reception on board this evening.

Day 2 Soufrière, St. Lucia

In Soufrière, wander a canopied haven of vivid flora in Diamond Falls Botanical Gardens, cultivated since the 18th century, past rocks tinted yellow, green and purple from the falls’ mineral-rich waters. At Sulphur Springs, witness firsthand ongoing geological activity in the dormant crater of Soufrière Volcano.

Day 3 Rodney Bay

Experience beautiful Rodney Bay, full of scenic views and friendly people. The view of St. Lucia’s twin volcanic peaks—the Gros Piton and Petit Piton, together part of a UNESCO World Heritage site—is majestic and iconic.

Day 3 Terre-de-Haut, Îles des Saintes

Arrive at Îles des Saintes, also known as Les Saintes, a small, charming archipelago. Enjoy a day at leisure and stroll the quaint streets of Terre-de-Haut, lined with bistros, cafes and shops, or walk to the beach to swim or snorkel.

Gather on deck for a barbecue dinner under a bright blanket of stars (weather permitting).

Day 4 Fort-de-France, Martinique

The most heavily French-influenced of all the Caribbean Basin, Martinique celebrates its Creole heritage amid idyllic scenery. In Fort-de-France, see the varied architectural styles of its historical buildings, including the elaborate Romanesque Schoelcher Library. Admire the verdant Pitons du Carbet from the Sacré Coeur de Balata, a reduced replica of the Basilica of Montmartre in Paris.

At the Balata Gardens, watch effervescent hummingbirds feed on sweet nectar. Stroll through a shaded canopy of trees, amid 3,000 varieties of tropical plants.

Later admire distinct Creole architecture and vast sugarcane fields at the Clément Plantation, a French historical landmark and producer of Clément rum for more than 125 years. Tour the former distillery and see the manor house, notable as the site of the 1991 post‑Gulf War meeting between French President François Mitterand and U.S. President George H. W. Bush.

Day 5, Morning Kingstown, St. Vincent and the Grenadines

Enjoy sweeping vistas of the Caribbean Sea and the capital city of Kingstown from the early‑19th‑century ruins of Fort Charlotte, built atop a steep promontory.

Walk among the largest botanical gardens in the Western Hemisphere, populated with trees from around the world and look for the endangered St. Vincent parrot. Kingstown is replete with historical architecture, including 19th‑century cathedrals

Day 5, Afternoon Admiralty Bay, Port Elizabeth, Bequia

Bequia is the largest island of St. Vincent and the Grenadines. Enjoy spectacular views of yacht‑filled Admiralty Bay from the remains of 18th‑century Hamilton Fort. Visit Mt. Pleasant, Bequia’s highest accessible point, for its amazing views.

Day 6 St. George’s, Grenada

Grenada’s volcanic isle enjoys cool breezes perfumed with fragrant exports—salt air swirled with nutmeg, cinnamon, cloves, mace, allspice, wild coffee and organic cocoa.

See historical landmarks in the picturesque capital, St. George’s, including Fort George. Enjoy panoramic views of the Carenage, a scenic waterfront dotted with colorful fishing boats and Georgian‑style architecture.

Walk among cinnamon, clove and bay trees in an herb and spice garden, where ginger, pepper and turmeric also grow, and learn about rare botanicals, such as zebapique and jump-up-and-kiss-me, used in cooking, traditional remedies and liqueurs.

Visit Grenada’s largest rum distillery and savor regional, impeccably aged rum. This afternoon, stroll the white-sand shores of Grand Anse Beach at your leisure.

Day 7 St. Vincent and the Grenadines / Tobago Cays

Ship arrives Tobago Cays, Grenadines. An ideal snorkeling retreat shielded from the sea by Horseshoe Reef, Tobago Cays Marine Park is an underwater gallery of colorful sponges, conchs, sea turtles, butterflyfish and parrotfish.

Attend the Captain’s Farewell Reception this evening.

Day 8 Bridgetown, Barbados / U.S.

Disembark in Bridgetown and transfer to the airport for your return flight to the U.S. or Canada.