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Charter Destination The Leeward Islands

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Experience the essence of Caribbean beauty with a superyacht charter in the Leeward Islands. Spanning over 150 miles from Anguilla in the north to Dominica, the Leeward Islands offer a fascinatingly diverse selection of islands to explore. With excellent transport links and a well-developed yachting infrastructure, whether you seek a family adventure or an upscale celebration, the Leeward Islands are a perfect destination for a luxury yacht charter.

The Leeward Islands are a paradise for water sports enthusiasts, with excellent conditions for everything from windsurfing and kiteboarding to deep-sea fishing and scuba diving. The coral reefs are teeming with life, and there are numerous wrecks and dive sites to explore. If you’re looking for a more relaxed experience, you can simply drop anchor in a secluded bay and soak up the sun or swim in the crystal-clear Caribbean Sea.

When it comes to dining, the Leeward Islands offer an incredible range of options, from beachside shacks serving up local specialities to high-end restaurants helmed by Michelin-starred chefs. The local cuisine blends African, European, and Caribbean influences, with fresh seafood, tropical fruits, and spices taking centre stage. And if you’re in the mood for a party, the Leeward Islands are home to some of the liveliest nightlife in the Caribbean, with beach bars, clubs, and casinos.

The Leeward Islands offer outstanding natural beauty and are steeped in history, offering an inviting balance of Caribbean spirit and laidback luxury; where each island offers something unique to discover. Charter a luxury motor yacht or harness the power of mother nature aboard an elegant sailing boat and discover this paradisical destination in style.


Amongst the best Leeward Islands to drop anchor at are Antigua, Saba, St. Eustatius, St. Maarten, St. Thomas, Anguilla, Virgin Gorda, and St. Barts.



Spend a few days discovering the best of Antigua’s 365 beaches and sail into the famed English Harbour. The island’s unmistakable British ambience provides a window into a captivating and diverse history. One of the most significant historical landmarks is the UNESCO-protected Nelson’s Dockyard in English Harbour. As the oldest Georgian harbour still operational, it is the focal point for Antigua’s annual Sailing Week, a prominent event on the yachting calendar. The beaches are the island’s primary attractions, but its appeal also lies in its maritime history – combined, they have placed the island in pole position on the Caribbean map.

The Leeward Islands, Antigua


Our Leeward Islands yacht charter itinerary would be incomplete without mentioning the tiny island of Saba, which lies to the northwest. Saba boasts towering cliffs and volcanic peaks that rise out of the Caribbean Sea, creating a stunning coastline to cruise. While there are no beaches to speak of, diving and snorkelling are world-class. Hike into the island’s interior, and explore the lush rainforest teeming with life. Alternatively, explore the peaceful capital named The Bottom.

Leeward islands, Saba


Nearby St. Eustatius, or “Statia” as it’s affectionately known, is an undiscovered gem. With its charming capital Oranjestad and fascinating yet poignant history that includes everything from pirates to the slave trade, chartering a yacht opens up precious opportunities to visit these lesser-known Caribbean treasures.

Leeward Islands, St. Eustatius


The bustling island of St. Maarten brings a distinctly cosmopolitan vibe, making it a must-visit on a Leeward Islands yacht charter. Divided into French and Dutch territories, St. Maarten’s Dutch side boasts a lively nightlife scene with casinos and nightclubs, while on the French side, gourmet cuisine and long, lazy days and French-influenced dinners are plentiful. The island’s cultural mix matches its diverse scenery, with European-style cafes and chic boutiques lining whitewashed Caribbean beaches. The adventurous can even follow a crew-led mission to the 424m-high Paradise Peak or fly above a mango plantation on an extreme zip line.

St. Maarten, Leeward Islands


As you step ashore at St. Thomas, you’ll be welcomed by the sights and sounds of one of the Caribbean’s most vibrant and sophisticated islands. A lively party atmosphere is guaranteed with an array of bars, clubs, and restaurants catering to every taste and mood. And for those who love to indulge in a little retail therapy, the island’s tax-free shopping is an absolute must.

St. Thomas is not just about partying and shopping. Indeed, the island boasts a rich and fascinating history, dating back to the days of pirates and colonial sugar plantations. There are plenty of opportunities to explore the island’s past, with historical sites and museums that offer a glimpse into St. Thomas’s intriguing past.

 St. Thomas, Leeward Islands


Anguilla, a British Overseas Territory, is also worth discovering during your Leeward Islands yacht charter. The island’s natural beauty, including some of the best beaches in the world, has been preserved while still offering luxurious retreats and a range of activities for superyacht charter guests to enjoy.

Sailing along the island’s idyllic coastline, one can enjoy the crystal-clear waters and spot the native red-billed tropicbirds. Anguilla’s rich wildlife and impressive wrecks and coral reefs below the waves, provide endless options for activities for yacht enthusiasts. Join local islanders and dance to live reggae on the powdered sugar sands of Shoal Bay or participate in one of Anguilla’s regular regattas.

Beyond the beaches, Anguilla offers rugged landscapes to explore, and golf enthusiasts will appreciate Anguilla’s golf course designed by golf legend Greg Norman. Take a day trip to Prickly Pear Cays, a truly secluded island just off Anguilla’s western coast, or visit the protected areas of Big Spring Cave, known for its prehistoric petroglyphs, or East End Pond, a wildlife conservation site.

With its unspoiled innocence and laid-back atmosphere, Anguilla is a destination that exudes the casual, low-key elegance that discerning travellers seek. Whether you’re sipping a rum punch while gazing out at the famous Shoal Bay sunset or enjoying the island’s many other charms, Anguilla is a place that will captivate your senses. And now, with a superyacht marina in development, Anguilla is quickly becoming a favourite among the yachting crowd.

Anguilla, Leeward Islands


Anguilla isn’t alone as a destination that appeals to those seeking sun-soaked adventure and tranquil escapes. The next recommendation on our Leeward Islands yacht charter itinerary is nestled among the British Virgin Islands. Virgin Gorda is a superyacht charter destination that beckons with its plethora of scenic beaches, stunning coral reefs, and world-renowned resorts. For those who wish to explore the Caribbean in style and luxury, Virgin Gorda is an excellent choice. Whether you want to indulge in the ultimate relaxation or seek out thrilling watersports, this island paradise has it all.

Virgin Gorda’s scenic charm extends beyond its stunning coral sand beaches though. The island’s interior is dotted with hidden treasures, such as the ruins of the Spanish fortress at the Little Fort National Park and the National Parks at Devil’s Bay, North Sound, Spring Bay and Gorda Peak. The island is also home to one of the world’s top 10 wreck dive sites – the RMS Rhone – a must-visit for avid divers.

Leeward islands, Virgin Gorda


St. Barts, the ‘it’ island with red-tiled roofs, French cuisine, and high-end boutiques, offers the most luxurious experience of all the isles. With every amenity expected of exclusive resorts, including excellent restaurants and designer boutiques, this unique and sophisticated island exudes a South-of-France feel with a tropical backdrop.

A short cruise south, berth in the fully serviced Christophe Harbour in St. Kitts. Perfectly positioned to the south of the island for access to the capital Basse Terre and an abundance of historical sites. Step ashore and discover rolling sugarcane fields, plantation ruins, and merchant houses now home to boutique hotel properties for a fascinating insight into this stunning island’s colonial past.

Leeward islands, St barts

A Leeward Islands yacht charter is an unforgettable experience, offering a unique blend of luxury and adventure in one of the world’s most beautiful destinations. Whether you’re seeking relaxation, adventure, or a little bit of both, the Leeward Islands truly have it all.

Why Visit?

  • Beautiful beaches
  • Big game fishing
  • Chic boutiques
  • Vibrant nightlife
  • World class restaurants
  • Wreck diving