Caribbean Windward Leeward Islands Cruise

Set sail on a true bluewater legend and discover the Caribbean the way it was meant to be experienced — under canvas, horizon wide open, and island lights twinkling at anchor.

Your journey begins in vibrant Rodney Bay, the yachting heart of Saint Lucia. After a welcome briefing aboard a Swan 51—a yacht synonymous with uncompromising build quality, refined Scandinavian craftsmanship, and a formidable offshore racing pedigree—you’ll feel immediately that this is no ordinary charter.

The Swan 51, built by Nautor Swan, is renowned for its balance, seaworthiness, and performance in serious ocean conditions. Designed for those who appreciate precision sailing, she delivers both exhilarating passages and exceptional onboard comfort.

Day 1–2: St Lucia → Martinique

We clear Rodney Bay and set a northerly course toward Martinique. Expect a spirited beam reach across turquoise waters. Martinique blends French sophistication with Caribbean rhythm—charming anchorages, world-class boulangeries, and lush volcanic landscapes. Evenings are spent beneath dramatic green hills.

Day 3–4: Martinique → Dominica

Next we sail toward the untamed beauty of Dominica, often called “The Nature Island.” Towering mountains plunge into the sea, waterfalls cascade through rainforest valleys, and the scent of spice hangs in the air. This is raw Caribbean—authentic, dramatic, unforgettable. The fortunate can get a glimpse of the rare sperm whale pod cruising these exceptional waters.

Day 5: Dominica → Îles des Saintes

A shorter but spectacular passage takes us to the idyllic archipelago of Îles des Saintes. French-Caribbean charm defines this stop: pastel houses, quiet anchorages, and panoramic views from hilltop forts. Swim in crystalline bays or wander cobbled streets with a café in hand.

Day 6: Îles des Saintes → Guadeloupe

We continue to Guadeloupe, a butterfly-shaped island rich in Creole culture and dramatic scenery. Explore vibrant markets, hike through tropical forests, or relax on secluded beaches. Under sail, the Swan 51 comes alive in the steady trade winds.

Day 7–8: Guadeloupe → Antigua

Our final offshore leg brings us to Antigua and Barbuda, famed for its sailing heritage. We conclude in historic Nelson’s Dockyard, a beautifully restored Georgian naval base and UNESCO World Heritage Site. Mooring here feels like arriving at the spiritual home of Caribbean yachting.

A final evening toast marks the completion of a remarkable island-hopping passage through some of the Caribbean’s most storied waters.

The Experience

8 days / 7 nights aboard a Swan 51

– Professional, experienced skipper included
– All yacht operating costs covered (fuel, marina fees, insurance, onboard provisioning basics)
– Hands-on sailing encouraged for those who wish to participate
– Small group, performance-oriented cruising
– Flights and travel to/from the Caribbean are not included.

This is not a cruise ship holiday. It is a sailor’s voyage — powered by trade winds, shaped by seamanship, and defined by the rhythm of the sea.
If you’re ready to experience the Caribbean as it was meant to be explored, step aboard.