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Windward Islands Flotilla

OCSC's Windwards Flotilla

The Windward Islands are an intensely tropical paradise. Rich history, volcanoes, isolated beaches, lush mountains, coral reefs and an amazing sailing experience all await your Caribbean arrival.

The Flotilla begins at the Moorings' base nestled in the dense tropical vegetation of Marigot harbor, St.Lucia (also known as "the Jewel of the Windwards"). Within a couple of hours, you’ll be underneath the towering Pitons, majestic volcanic peaks rising over 2,000 feet from the water’s edge.

Reach the pinnacle of your destination experience as you enter the Tobago Keys – four small sandy shore islands in shallow waters protected by a four-mile long horseshoe barrier reef. In OCSC's experience, this is one of the most beautiful anchorages in the Caribbean.

Canouan is the last point of call – Moorings' new base, in the heart of the Grenadines.

Retail Rate Member Rate


OCSC Members & Repeat OCSC Adventurers save 5%!