Home > Destinations > Caribbean Yacht Charters - Windward Islands

Located on the southern end of the Caribbean chain, the Windward Islands are the Caribbean's best-kept yacht charter secret. These lush and richly tropical volcanic islands are a little peace of France, floating amongst the palm lined sandy beaches and misty rain forests of the Caribbean. The Windward Islands yacht charter area runs from Dominica in the north, to Grenada in the south. The Windward Islands also include the islands of Martinique, St. Lucia, St. Vincent and the Grenadines and Barbados.

This jewel area of the Caribbean hosts yacht charters year-round, with a rainy season from July through October. From its distinctive cuisine to its language, The Windward Islands exude the ambiance of Paris with the warmth, friendliness and spice of the West Indies.

As with most of the Caribbean, The Windward Islands yacht charter season runs from November through July. The primary high season is from mid-December to March, when the winter escapees from North America and Europe arrive in their greatest numbers. The hurricane season is from late July to early October. Although hurricanes are generally rare, this is the least expensive time for Windward Island yacht charters and there are some really good deals available. However, as well as running the risk of storms, this time of year also tends to have lighter (or non-existent) winds.

Of volcanic origin, the islands are generally rugged, mountainous, and well forested, and they have many streams and lakes. With an equable climate, ample rainfall, and rich soil, they produce a variety of tropical agricultural crops for export, including bananas, spices, limes, and cacao. The deep and sheltered harbors encourage considerable inter-island commerce. Fort-de-France, on Martinique, and Castries, on Saint Lucia, are the islands' chief cities. The islands are largely inhabited by descendants of Africans, who were brought as slaves during the colonial period. The culture varies from island to island, but the French influence is particularly strong.

Allow us to custom tailor your luxury, crewed Windward Islands yacht charter. Our knowledge of Caribbean charter yachts, crews, destinations and cruising itineraries is unmatched! We personally inspect each yacht, meet the captains, sample the chefs' cuisine and evaluate the service offered by each yacht crew.

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Sample Windward Island Yacht Charter - St. Lucia to Union Island, including St. Vincent and the Grenadines

Day 1: Your charter yacht awaits you at Marigot Bay, a small, sheltered anchorage known for excellent sunset rum punches.  Enjoy an afternoon swim and dinner aboard.

Day 2: Head south to Soufriere, a small town dominated by the towering twin Pitons, and take a walk in the rain forest or explore the sulphur springs. Enjoy lunch and a swim before leaving for St. Vincent on a beautiful broad reach of about 30 nautical miles.

Day 3: Enjoy lunch at Cumberland Bay, where a forest of coconut and banana trees flows down the valley to the beach. Enjoy the towering mountains and craggy peaks as you motor your luxury charter yacht along the steep and wild terrain of St. Vincent.   Arrive at Young Island for a swim and cocktails before dinner and an overnight stay.

Day 4: Leave early for Bequia. Once an active whaling station, Bequia offers a fun, tropical marketplace and sought after hand-carved wooden sailing boats.  Enjoy your first night at anchor in Admiralty Bay, and step a shore to visit the well know Frangipani Hotel for cocktails on the lawn overlooking the bay.

Day 5: After breakfast pull up anchor for Mustique.  An exclusive island for the rich and famous, visit Basil’s Bar, rent a Moke or a horse to explore, or dive a few of the shipwrecks in the waters around the island.

Day 6: Leave early for a sail to Canouan and relax in a peaceful anchorage off Charlestown Bay for a quiet lunch, before going ashore to explore. Sail to Tobago Cays after lunch, considered the best snorkeling and diving in the Grenadines and enjoy a beautiful night under the stars.

Day 7: Leave for Palm Island and wade along Casuarina Beach, a gorgeous expanse of golden sand and turquoise water.  Enjoy a cocktail at the Sunset Bar before heading back to the yacht for dinner.

Day 8: After breakfast motor to Union Island for your flight home, ending your luxury Windward Islands yacht charter.