Luxury Caribbean Yacht Charter: Leeward Islands

Exploring The Leeward Islands

A yacht charter in the Leeward Islands offers one of the most captivating and diverse experiences in the Caribbean. Stretching between Puerto Rico and Dominica, this chain of volcanic islands is named after the trade winds that sweep across its turquoise waters. A Leeward Islands yacht charter is unlike any other Caribbean itinerary, combining French elegance, colonial history, vibrant culture, and untouched natural beauty.

Unlike the Mediterranean, with its cosmopolitan ports and ancient ruins, the Leeward Islands deliver a perfect mix of luxury, adventure, and relaxation. Guests can explore designer boutiques one day, dive pristine reefs the next, or unwind on pink-sand beaches far from the crowds. 

We, at Moncada, provide a carefully curated itinerary to ensure that our guests can experience the true beauty of the Leeward Islands. They can explore the heart of the Caribbean by visiting Antigua and Barbuda and travel to more exclusive islands such as St Barts and Isle Fourchue.

Discover the Distinctive Leeward Islands

Each island in the Leeward Islands has its own character, making a Caribbean yacht charter adventure truly unique. Our charters allow guests to explore both iconic hotspots and hidden gems, all with the 5* comfort and service of a luxury superyacht.

Antigua

Antigua is the heart of Caribbean yachting, with 365 beaches and world-class facilities in Nelson’s Dockyard and English Harbour. Guests can enjoy watersports like jet-skiing, paddleboarding, or sailing in calm bays. The evenings are perfect for waterfront dining followed by cocktails under the stars, making Antigua a quintessential destination for your Leeward Islands yacht charter. Beyond the harbours, the island’s charm unfolds at the vibrant Shirley Heights Lookout, where steel drum bands play as the sun sets over the bay. Fine dining options like Sheer Rocks and Catherine’s Café bring European flair to Caribbean ingredients, while local markets in St. John’s offer handmade crafts and island spices that reflect Antigua’s deep maritime heritage.

Barbuda

Barbuda offers unparalleled tranquillity with 11 miles of pink-sand beaches, ideal for guests seeking privacy. Yachts anchor in serene bays where the only sounds are waves and seabirds. Visitors can explore the Frigate Bird Sanctuary, enjoy beach barbecues prepared by the yacht chef, or dive into vibrant coral gardens. For anyone seeking a serene escape, Barbuda exemplifies the allure of a Caribbean yacht charter adventure. The island also invites exploration of its unique caves and sinkholes, such as the Two Foot Bay Caves, filled with ancient Arawak petroglyphs. Guests can visit the small community of Codrington to experience local fishing traditions and sample freshly caught lobster at Uncle Roddy’s Beach Bar, a favourite among visiting yacht guests.

Saint Kitts & Nevis

These twin islands combine natural beauty with colonial history. Saint Kitts is famous for Mount Liamuiga hikes and Brimstone Hill Fortress, a UNESCO World Heritage site, while Nevis offers hot springs, plantation resorts, and slow-paced island life. Together, they provide an ideal balance of exploration and relaxation for yacht charter guests. Visitors can ride the scenic St. Kitts Railway through lush hillsides or explore the colourful streets of Basseterre lined with local craft markets. On Nevis, Bananas Restaurant and Golden Rock Inn offer fine dining amid tropical gardens, while heritage sites like the birthplace of Alexander Hamilton reflect the island’s fascinating colonial past.

St. Eustatius (Statia)

Statia is one of the most authentic stops for a Leeward Islands yacht charter. Its marine park attracts divers with volcanic reefs and shipwrecks, while the historic town of Oranjestad showcases 18th-century architecture. Statia offers a quieter, intimate experience, providing a contrast to the glamour of St. Barts or St. Martin. Guests can visit the small museums and restored warehouses that tell stories of the island’s role as the “Golden Rock” of Caribbean trade. Hikers can explore the Quill Volcano, a lush crater filled with exotic flora and panoramic views, or enjoy local dishes made with island-grown produce at Blue Bead Bar & Restaurant, a long-time favourite amongst divers and sailors.

St. Barts & Isle Fourchue

St. Barts is synonymous with luxury, French cuisine, and designer shopping in Gustavia. Guests on a yacht charter can anchor in turquoise waters at Colombier Beach or explore Isle Fourchue, a rugged, uninhabited island perfect for private snorkelling, paddleboarding, and picnics. This combination of elegance and seclusion makes St. Bart’s an ideal destination on a Caribbean yacht charter. The island’s dining scene is world-renowned, with iconic spots such as Le Tamarin and Bonito offering refined menus in lush, tropical settings. Beyond the glamour, guests can explore the island’s cultural side at the Wall House Museum or visit artisanal boutiques where French-Caribbean craftsmanship takes centre stage.

St. Martin/Sint Maarten

Split between French sophistication and Dutch liveliness, St. Martin/Sint Maarten is an ideal stop for a yacht charter in the Caribbean. The French side offers gourmet dining and calm anchorages, while the Dutch side boasts casinos, nightlife, and duty-free shopping. Iconic Maho Beach provides the thrill of low-flying planes, adding an unforgettable element to any yacht charter. Visitors can also explore Grand Case, known as the “Gourmet Capital of the Caribbean”, home to renowned restaurants like L’Auberge Gourmande and Le Pressoir. On the Dutch side, Philipsburg’s boardwalk features local rum shops, art galleries, and a lively marina scene where Caribbean music and culture come to life.

Anguilla

Anguilla offers calm anchorages, powdery white beaches like Shoal Bay, and a growing reputation for gourmet cuisine. Guests can swim, paddleboard, or enjoy beachfront lobster dinners under the stars, experiencing understated luxury in one of the Caribbean’s most refined settings. The island is celebrated for its relaxed sophistication, where spots like Blanchard’s Beach Shack and Veya Restaurant combine fine dining with island charm. Visitors can also explore the island’s thriving arts scene, with galleries showcasing local painters and sculptors, or visit the Sandy Ground salt pond, a reminder of Anguilla’s early salt-trading heritage.

Why Choose a Leeward Islands Yacht Charter

A Leeward Islands yacht charter combines the best elements of Caribbean cruising: chic harbours, secluded beaches, historic towns, and natural beauty. Compared to other destinations, the Leewards provide a balance of glamour, adventure, and relaxation. Guests can alternate between designer shopping and secret coves, coral reef diving and gourmet dining, or bustling French ports and untouched pink-sand beaches. 

This diversity makes yacht chartering in the Leeward Islands unmatched: guests enjoy both luxurious indulgence and authentic Caribbean experiences in a single journey.

The Essence of a Yacht Charter in the Leeward Islands

With Moncada, a Leeward Islands yacht charter experience offers unforgettable contrasts: lively harbours, serene anchorages, pristine reefs, and beaches where the only footprints are your own. From St. Barts’ glamour to Barbuda’s seclusion and Statia’s historical charm, every stop reveals a new side of the Caribbean.