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The Cosmopolitan Caribbean Destination - Leeward Islands Yacht Charter

Called the Leeward Islands, these three major islands and the numerous islets that are scattered near them offer a welcoming blend of cultures, lifestyles, and landscapes. You'll experience the French flavor of St. Barth's and St. Martin, the Dutch influence on St. Maarten, and the British background of Anguilla. Easy to access from both the U.S. and Europe, the islands have all of the essential ingredients of an incentive travel program – spa, casino, golf, world class dining and shopping with the added WOW factor of a private luxury yacht fleet and an a Leeward Islands yacht charter itinerary that is 110% customized to your preferences.

Some splendid ports of call on a Leeward Islands yacht charter itinerary include:

St. Maarten/ St. Martin

One island, yet two countries and two languages. One Dutch, one French and both with a West Indian blend. This island has it all - shopping, golf, casinos, discos, beaches, and stunning scenery. Marigot on the French side has an abundance of boutiques with the latest in European and tropical fashions. The open air market at the harbor bustles with the selling of fresh foods and local crafts. Both Marigot and nearby Grand Anse have sidewalk cafes serving French, Creole and West Indian Cuisine. Or you can saunter down a side street for some roast pig or chicken being barbecued in the open air by some locals during your St Martin yacht charter trip. Phillipsburg on the Dutch side is the hub of duty free shopping with dozens of shops selling jewelry, perfume, island handicrafts, souvenirs, linens, and crystal.

St. Barth's

Anyone who has ever been to St. Barth's agrees - it is captivating and magical. A charming flavor of France in the midst of the Caribbean Sea. The fragrance of frangipani in the air, the banter of the French West Indian accents, the smiling faces of the people on the streets, the scent of croissants, the hint of celebrities on the island... all add to its allure. On your St Martin yacht charter itinerary, the main port, Gustavia, rises gently up the hillside from the water's edge with boutiques and fine restaurants throughout. The beaches of the island are superb and never-ending. Baie de Colombier offers great snorkeling and pristine natural beauty, and the nearby island of Ile Fourche is a nature lover's paradise.


Anguilla is laid back island with its own distinct geography and culture. It is a low lying island edged with pristine beaches and coral reefs teeming with fish. You won't find any cities or major villages here. Instead, there's a sprinkling of cottages and world class resorts scattered about the island with farm animals roaming freely along the mostly dirt roads. But even outposts have their watering holes, and Road Bay on the North side is often pulsating with calypso and reggae rhythms. Our St Martin Yacht Charter guests can enjoy golf at the Greg Norman designed course at Temenos Resort or indulge in a spa morning at Cap Jaluca or Viceroy.

Prickly Pear Cays

A litter of islands off of Anguilla where the preservation of natural beauty is evident. An absolute must for snorkeling and beaching during a Leeward Islands yacht charter trip.


A long stretch of sunsplashed beach that melts into turquoise waters... an ancient site of celebration for the Arawak Indians... a place for us to lull the afternoon away.

The Leeward Islands are farther apart than in the BVI so sailing distances from port to port can be slightly longer. The seas are not as protected as in the BVI and can be more robust in the winter months. This is not an issue on our larger yachts, but if you are chartering a smaller yacht, Spring, Summer and Fall are ideal times to embark on a Leeward Islands yacht charter trip.

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