Leeward Islands Yacht Charter Guide for 2024-2025

Sailing the Leeward Islands

Discover the secrets of St. Martin, St. Barths, Anguilla, and Antigua as you vacation on your luxury yacht charter in the Leeward Islands

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

The Leeward Islands are an eclectic collection of volcanic island formations that lie to the east of Puerto Rico and the Virgin Islands. Part of the Lesser Antilles and arguably one of the most beautiful destinations in the world, the Leeward Islands are a perfect choice for your next yacht charter. As you explore each of these distinct locales, expect to find unspoiled private beaches, chic shops, superb restaurants, and stunning coastlines.

With everything from secluded island paradises to lively towns with thriving nightlives, discover the perfect escape on board your Leeward Islands charter holiday. There is no better way for you and your family or friends to experience these waters.

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St. Martin

Philipsburg,Sint Maarten
Philipsburg, Sint Maarten

As the center of yachting and yacht racing in the Caribbean, St. Martin is the ideal destination to embark upon your Leeward Islands yacht charter. The island has a rich history and currently boasts dual French and Dutch nationality. In fact, the island is divided almost in half between the countries, and as a result, there is a fantastic mixing of cultures, with everything from French boulangeries to enticing Dutch beach clubs, there is something for everyone here. 

You can fly into Princess Juliana International Airport and make a simple transfer to the waters of Simpson Bay, the Caribbean's largest lagoon. It is the perfect place to embark and set out upon your bespoke charter vacation. With nightclubs and fine dining available on the Dutch side and classical Caribbean towns like Marigot on the French, there is so much to discover here. 

Anywhere you venture on this island, you will find beautiful beach resorts and have the opportunity to get a taste of the Caribbean lifestyle. For more information about the island check out our St. Martin Yacht Charter Guide or reach out to one of our Charter Experts to start planning your perfect getaway.

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St. Martin Charter Types


St. Barths

St Barths
Stunning St. Barths

St. Barths is a small yet highly desirable luxury charter destination with delicious food and wine, and an unmistakable sense of style and fashion. The island brings a new flavor of sophistication to the relaxed atmosphere of the Bahamas, making this paradise like a taste of the Mediterranean. This chic island is home to gorgeous, unpopulated beaches, fine restaurants, and fashionable shopping, and with Gustavia Harbor docking up to sixty yachts (200’ maximum) in the inner harbor and another 100+ anchorages in the outer harbor, there is no better time to charter a yacht in St. Barths. 

For more than forty years the island has hosted the annual St. Barths Music Festival showcasing the best musicians, singers, and composers from renowned orchestras. Charter a yacht and live in unrivaled comfort as you listen to the finest music in the world. 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 all over for you to discover, your visit to St. Barth's will be unforgettable. Find out more about chartering a crewed yacht from St. Barths or including it in your bareboat itinerary by visiting our St. Barths Yacht Charter Guide.

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St. Barths Yacht Charter Types 


Anguilla

Caribbean blue waters and palm trees in Anguilla
Secluded beach, Anguilla

With its plethora of secluded beaches, Anguilla was one of the Caribbean’s best-kept secrets, but it is slowly becoming one of the most exclusive and sought-after destinations in the region. This British island will have you driving on the left side of the road and enjoying the palpable friendliness of the locals as you explore its hidden corners and relax on the beaches. Known as the culinary capital of the Caribbean, you are certain to find delectable cuisine and unmatched comfort in any of the restaurants on the island. 

Charter clients can fly into the Anguilla airport directly now that the airport has been expanded for private jets or Anguilla is just six miles and twenty minutes by boat to the north of St. Martin and Princess Juliana International Airport. Once you are there, head to West End Bay for stunning sunsets, and cliff-top hikes, or while away the hours swimming the shallow waters of Forest Bay. 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 or reach out to one of our Charter Experts.


Antigua

Antigua is home to 365 beaches and an exciting colonial history with the island's main harbor featured in the famous book Nelson's Navy.  This island is a must-see destination in the Caribbean and the perfect place to begin your dream yacht charter holiday. Surrounded by colorful coral reefs, and thriving schools of fish, Antigua is the perfect place to explore below the waves and get up close to nature. Whether you want to snorkel or dive, many of our crewed charters include equipment for exciting expeditions! Visit the bustling town of St. Johns for fabulous shopping and some of the best dining experiences in the Caribbean.

On your charter, venture over to the nearby uninhabited island of Barbuda and experience its vibrant tropical wildlife and stunningly secluded beaches where you can disconnect from the outside world. Find your own piece of paradise here and watch one of the most beautiful sunsets in the world from the beach or your yacht. 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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Antigua Yacht Charter Types


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 dinner on board with your group, as it is to find the many restaurants and bars for late-night entertainment. If you would like any suggestions about where to go or what to fo in the Leeward islands, or any other yacht charter destinations, please feel free to get in touch with one of our Charter Experts.

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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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