A charter through the Leeward Islands offers a refined mix of untouched nature, rich colonial history, and high-end Caribbean culture. From the refined harbors of Antigua and the wild cliffs of Saba, to the glamor of St. Barths and the barefoot elegance of Anguilla, this ten-day itinerary offers an unforgettable Caribbean escape. The best time to visit is between December and May, when the trade winds are steady, and the seas are ideal for cruising.
Begin your charter in Falmouth Harbour, one of Antigua’s most prestigious yachting hubs, known for its vibrant marina village and proximity to Nelson’s Dockyard, a UNESCO World Heritage Site. After boarding, spend your first afternoon cruising Antigua’s southern coastline or relaxing in the harbor. Enjoy a sunset cocktail on deck or ashore at Pillars, a refined waterfront restaurant nestled beneath limestone cliffs.
Cruise northwest to Nevis, a serene island with a rich history and laid-back Caribbean feel. Visit Charlestown to explore colonial architecture, or enjoy horseback riding along the beach. Anchor near Pinney’s Beach for a relaxed beach setup or a long lunch at Four Seasons Nevis, where luxury meets unspoiled natural beauty.
Cross the channel to St. Kitts, a lush island dominated by the volcanic peak of Mount Liamuiga. Explore the island’s rainforest trails or tour the Brimstone Hill Fortress, another UNESCO World Heritage Site. If time allows, stop for snorkeling at Shitten Bay, a popular spot with clear waters and vibrant reefs.
Known locally as Statia, this island is a hidden gem, steeped in Dutch colonial history and blessed with quiet anchorages. Divers will find a treat in the underwater ruins and coral-encrusted shipwrecks that lie just offshore. Enjoy a quiet dinner on board under the stars.
One of the Caribbean’s most dramatic islands, Saba rises sharply from the sea with sheer cliffs and verdant rainforests. Hike the Mount Scenery trail, or dive the marine park’s vertical walls. There are no beaches here—just stunning natural beauty and rare biodiversity.
Arrive in Gustavia, the glamorous capital of St. Barths, known for its designer boutiques, gourmet restaurants, and stylish beach clubs. Spend the day at Shell Beach or cruise around to Colombier Bay for a private beach experience. Dine ashore at Bonito or L’Isola, two of the island’s most celebrated restaurants.
Continue enjoying St. Barths with a day dedicated to barefoot indulgence. Lounge at Nikki Beach or Le Toiny Beach Club, or explore the island by Mini Moke. The island’s French flair and flawless hospitality make every experience feel effortlessly luxurious.
Cruise north to Anguilla, renowned for its powdery white sands and turquoise bays. Anchor off Meads Bay or Rendezvous Bay, where the beach bars serve some of the best rum punches in the Caribbean. Enjoy snorkeling, kitesurfing, or a relaxed beach picnic.
Spend another day in Anguilla, exploring Shoal Bay, often listed among the world’s top beaches. Visit the offshore cays like Sandy Island or Prickly Pear, each with their own rustic beach bar and excellent snorkeling. This is Caribbean serenity at its finest.
Cruise into Simpson Bay or Port de Plaisance Marina on the Dutch side of St. Martin for disembarkation. Whether flying from Princess Juliana Airport or extending your stay ashore, your journey through the Leeward Islands ends surrounded by unforgettable beauty and the timeless rhythm of the sea.
Your vision is unique. Your charter should be, too. Speak directly with a specialist who will hand-select the perfect yacht, crew, and itinerary from the global fleet, customizing every detail, from the cruising grounds to the chef’s menu.
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