Leeward Islands Yacht Charter Guide for 2024 and 2025 | Caribbean

Sailing Leeward Islands

Discover St Martin, St Barths, Anguilla and Antigua on your Leeward Islands yacht charter vacation in the Caribbean

St Barths | St Martin | Anguilla | Antigua | Other Helpful Information

The Leeward Islands are a beautiful collection of islands that lie to the east of Puerto Rico in the Lesser Antilles of the Caribbean. Arguably some of the most beautiful yacht charter destinations in the world, the Leeward Islands are a perfect choice for your next yacht charter - expect to find unspoiled, private beaches to chic shops and superb restaurants.

With everything from secluded island paradise to lively towns and nightlife, we can help you to discover the ultimate Leeward Islands charter holiday for you and your family or friends.

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St Martin

Philipsburg,Sint Maarten

At the centre of the Caribbean yachting industry and with a stunning coastline, St Martin is the ideal destination to start your Leeward Islands yacht charter. Its dual nationality of French and Dutch makes for two diverse halves of the island and a vibrant culture to explore with everything from French boulangeries to the exciting Dutch nightlife. Berth in the marina of the Caribbean's biggest lagoon, Simpson Bay where you will find a luxury marina village incorporating everything you might need in a holiday destination including restaurants, shops, a swimming pool and tennis courts. Simpson Bay is also ideally located close to the Princess Juliana International Airport, meaning transfers from airport to yacht are simple and inexpensive.

Enjoy the classical Caribbean town of Marigot, once a quaint fishing port that is now lined with chic bistros and fresh food markets. On the Dutch side, discover beautiful beach resorts and fruity rum cocktails for a real taste of Caribbean life. See our St Martin Yacht Charter Guide for more information on the island.

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St Barths

St Barths

St Barths is a small, yet highly desirable luxury charter destination where the food and wine are delicious and the sense of style and fashion, unmistakable. The island has been, for some time, a destination for those seeking both relaxation and sophistication in the Caribbean…a true taste of the Mediterranean! Gustavia Harbor can now dock up to sixty yachts (200’ maximum) in the inner harbor with anchorages for another 100+ yachts in the outer harbor. The steep, mountainous island is home to gorgeous, unpopulated beaches, fine restaurants and fashionable shopping. For twenty-two years, St. Barth’s also hosts cultural events such as the annual Classical Music Festival which now has been expanded to include jazz and ballet.

This island will give you a taste of pure luxury, whether on board a modern motor yacht, a sailing yacht or a catamaran with secluded beaches and some of the best restaurants in the Caribbean, your visit to St Barths will be unforgettable. Find out more about chartering a crewed charter from St Barths or including it in your bareboat itinerary by visiting the St Barths Yacht Charter Guide.

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Caribbean blue waters and palm trees in Anguilla

With over thirty secluded beaches, Anguilla has been one of the Caribbean’s best-kept secrets but is becoming one of its most exclusive and sought after destinations. This is an English island where cars drive on the left side of the road and there is a palpable friendliness, making it a relaxing charter destination. Charter clients can fly into the Anguilla airport directly now that the airport has been expanded for private jets. Alternatively, Anguilla is just six miles to the north of St. Martin and reachable in about 20 minutes by boat.

Head to West End Bay for perfect privacy, stunning sunsets and cliff-top hikes or while away the hours in the shallow waters of Forest Bay, perfect for swimming along with another beautiful beach. With miles of empty beaches, even in the height of the season, you will feel truly relaxed and at one with nature exploring the shores of this beautiful island. For more information on charters available from Anguilla visit our Anguilla Yacht Charter Guide.


This is an island of exciting colonial history, with the main harbor being that of Nelson's Navy as well as having 365 beaches, Antigua is not on a must-see island of the Caribbean, but also the perfect place to begin your dream yacht charter holiday. Antigua is surrounded by colorful coral reefs, perfect for those who enjoy exploring below the waves either snorkeling or diving - many of our crewed charters include equipment for such exciting expeditions! Visit the bustling town of St Johns, the capital of the island, for fabulous shopping and some of the best dining experiences in the Caribbean.

You may wish to visit the nearby and uninhabited island of Barbuda to experience its vibrant tropical wildlife and stunningly secluded beaches ideal for switching off from the outside world. Find your own piece of paradise and watch one of the most beautiful sunsets in the world from a beach or boat. If you want to find out more about chartering a yacht from Antigua, visit our Antigua Yacht Charter Guide to start planning your dream vacation.

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Other Helpful Information

There are infinite ways to spend your holiday in the Leeward Islands. It is important to match your (and your party's) desires and goals to the itinerary. It is just as easy to find a quiet cove each night for a peaceful diner on board with your group, as it is to find the many restaurants and bars for late-night entertainment. If you'd like any suggestions about the Leewards, or any other yacht charter destinations, please feel free to get in touch.

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Our Caribbean destinations: The Windward Islands | Antigua | British Virgin Islands | Grenada | Guadeloupe | Martinique | Spanish Virgin Islands | St Barths | Anguilla | St Martin/Maarten | St Lucia | St Vincent and the Grenadines | US Virgin Islands - St Thomas, St John, St Croix

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