14-Day Ultimate Leeward Islands Yacht Charter

Begin your Leeward Islands adventure in bustling St Martin, where Dutch and French cultures collide. Experience the legendary Maho Beach with its dramatic overhead plane arrivals, visit trendy beach clubs, or enjoy a marina dinner. Settle comfortably into your yacht and prepare for two weeks of Caribbean exploration.

Sail to pristine Anguilla, known for its unspoiled beaches and calm waters. Anchor at iconic Shoal Bay or serene Meads Bay, then dine at world-class restaurants like Blanchards or Cap Juluca. Experience the crystal-clear waters and laid-back luxury that define this hidden Caribbean gem.

Dedicate a full day to Anguilla's treasures, exploring Sandy Island and the Prickly Pear Cays. Snorkel pristine coral reefs, island-hop between uninhabited cays, and experience the unhurried pace of Caribbean living. This proper slow day allows you to truly absorb Anguilla's natural beauty.

Cruise to iconic St Barths and anchor in the picturesque port of Gustavia. Explore designer boutiques from world-renowned brands, relax at upscale beach clubs, and soak in the sophisticated island atmosphere. Watch the sun set over the harbor as yachts and locals create the perfect Caribbean scene.

Dedicate a full day to St Barths' most coveted beaches and establishments. Lounge at legendary St Jean or serene Gouverneur Beach, enjoy lunch at Nikki Beach or Shellona, and experience world-class nightlife or intimate waterfront dining. This is the peak of Caribbean beach culture.

Sail to volcanic Saba, a stark and stunning contrast to the sophistication of St Barths. Explore the Saba Marine Park with world-class diving opportunities, encounter untouched Caribbean nature, and experience the island's quiet charm. This is quintessential hidden Caribbean.

Begin a scenic cruising day as you transition toward the southern Leewards. Arrive in Basseterre with its colonial charm and vibrant port energy. Choose between beachside relaxation, historic exploration, or an intimate onboard evening to reflect on your journey so far.

Explore the dual-island experience of St Kitts and Nevis, staying in the upscale Nevis area near world-class resorts. Visit luxury beach clubs in the Four Seasons vicinity, take in the views of the historic Brimstone Hill Fortress, and experience the perfect blend of Caribbean culture and natural beauty.

Undertake a proper open-water cruising day as you sail to Antigua. Arrive in the historic English Harbour with its UNESCO heritage and active port atmosphere. Settle into this larger island and prepare for extended exploration with dinner at iconic waterfront establishments.

Dedicate a full day to discovering Antigua's 365 beaches—one for each day of the year. Visit the iconic Dickenson Bay and Half Moon Bay, explore the UNESCO heritage of Nelson's Dockyard, and blend Antigua's rich sailing history with world-class beach time and water sports.

Break up the journey back north with leisurely scenic cruising around Antigua's coastline. Make strategic swim stops at secluded coves and pristine beaches. Enjoy relaxed sailing and onboard time to reflect on unforgettable island experiences before returning to St Barths.

Return to St Barths for your final night, now as a seasoned explorer of the Leewards. Discover new beach clubs and dining spots you may have missed, indulge in world-class shopping, and enjoy the "buzz" of this most sophisticated Caribbean destination as your voyage concludes.

Sail back to St Martin for your final evening. Make one last swim stop en route to capture any remaining memories. Enjoy a relaxed farewell dinner onboard or ashore, toasting to an unforgettable 14-day journey through the Leeward Islands' finest experiences.

Bid farewell to the Leeward Islands and your floating sanctuary. Spend your final morning exploring any last corners of St Martin or simply enjoying breakfast on deck. Depart with memories of pristine beaches, world-class dining, dramatic volcanic islands, and unforgettable Caribbean magic.