Leeward Islands

St. Martin • Anguilla • St. Barts • St. Kitts & Nevis The Leeward Islands offer one of the Caribbean’s most rewarding yacht charter experiences, blending European sophistication with tropical beauty. Beginning and ending in St. Martin / Sint Maarten, this itinerary explores the pristine beaches of Anguilla, the glamour of St. Barts, the secluded waters of Île Fourchue, and the volcanic landscapes of St. Kitts & Nevis. Along the way, discover crystal-clear anchorages, exceptional cuisine, vibrant island culture, and some of the finest sailing grounds in the Caribbean.

 

Day 1 | St. Martin / Sint Maarten Board your yacht at noon in Simpson Bay, one of the Caribbean’s premier yachting centres. After a warm welcome from your captain and crew, settle into your luxurious surroundings and enjoy lunch on deck. Spend the afternoon exploring the island’s unique blend of Dutch and French influences, from the lively waterfronts of Simpson Bay to the boutiques, cafés, and markets of Marigot. As the sun sets over the Caribbean Sea, enjoy your first dinner aboard and toast the beginning of an unforgettable voyage.

Day 2 | Anguilla Following a leisurely breakfast, cruise to the neighbouring island of Anguilla, renowned for its powder-soft white-sand beaches and turquoise waters. Anchor off Shoal Bay or Road Bay and spend the day swimming, paddleboarding, snorkelling, or simply relaxing on pristine shores. For those wishing to explore further, the nearby Prickly Pear Cays offer exceptional marine life and untouched natural beauty. Enjoy a relaxed evening under the stars in one of the Caribbean’s most tranquil settings.

Day 3 | Grand Case, St. Martin Return to the French side of St. Martin and anchor in the beautiful bay of Grand Case. Widely regarded as the gastronomic capital of the Caribbean, Grand Case is famed for its blend of French cuisine and island flavours. Stroll along the waterfront, browse charming boutiques, and enjoy lunch at one of the village’s celebrated restaurants. Spend the afternoon swimming from the yacht before a memorable evening overlooking the bay.

Day 4 | Tintamarre & Île Fourchue Cruise past the unspoiled island of Tintamarre, where pristine beaches and protected waters provide excellent opportunities for swimming and snorkelling. Continue to Île Fourchue, a secluded and uninhabited island between St. Martin and St. Barts. Surrounded by crystal-clear waters and vibrant coral reefs, this peaceful anchorage is a paradise for snorkellers and divers. Spend the afternoon exploring the underwater world before enjoying dinner beneath a canopy of stars.

Day 5 | St. Barts A short morning cruise brings you to Gustavia, the elegant capital of St. Barts. Known for its chic atmosphere, designer boutiques, fine dining, and sophisticated beach clubs, St. Barts has long been a favourite destination for luxury travellers and yacht owners alike. Spend the day exploring the island, relaxing on one of its idyllic beaches, or enjoying lunch overlooking the harbour. In the evening, immerse yourself in the vibrant social scene that has made St. Barts one of the Caribbean’s most sought-after destinations.

Day 6 | St. Kitts & Nevis Set course south towards the twin-island nation of St. Kitts & Nevis. As volcanic peaks rise from the horizon, discover a Caribbean rich in history, culture, and natural beauty. Explore historic plantation estates, wander charming waterfront villages, or relax on the golden sands of Pinney’s Beach. Golf enthusiasts may wish to enjoy a round at the renowned Four Seasons Resort Nevis, while others can simply savour the islands’ relaxed atmosphere and spectacular scenery.

Day 7 | Return to St. Martin / Sint Maarten Enjoy a final day of cruising through the sparkling waters of the Leeward Islands as your yacht returns towards St. Martin. Spend the day enjoying watersports, swimming in secluded bays, or simply relaxing on deck while taking in the magnificent Caribbean scenery. On your final evening aboard, celebrate the journey with a farewell dinner prepared by your private chef as the sun sets on your Caribbean adventure.

Day 8 | St. Martin / Sint Maarten Enjoy a leisurely breakfast and a final morning aboard before disembarking at noon in Simpson Bay. With Princess Juliana International Airport just a short drive away, onward travel is effortless, bringing an exceptional Leeward Islands yacht charter to a close.