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Blue water sailing in the Caribbean

The Caribbean Season extends from mid-December to the end of April normally culminating with Antigua Classics.

Windward and Leeward Islands, the Greater Antilles.

The ‘ward’ you in fairly easy to define, when the British gained control of many of the Lesser Antilles, they designated Antigua, Montserrat and the islands to the north as the “Leeward Islands“. Guadeloupe and the islands to the south were designated as the “Windward Islands

Photo By David Stanley

The Greater Antilles.

The Great Antilles stretches from the Virgin Islands in the North West to Cuba and The Bahamas in the north.

As a sailor you will realize it’s easier to sail from the Windward Islands downwind to the Leeward Islands and on into the Antilles Chain, in essence many of our Caribbean voyages follow the principle.

Each year the selection of voyages is always changing, it may be the same vessel going to different islands or new vessels going to their wish list of wonderful islands.

Catch the sun, the rum and the rhythms of the Caribbean sea and music.

Cuba with Classic Sailing
cuba

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The Caribbean Sailing Voyages

Twister

Caribbean Island Hopping to St Martin TW150325

Embark

Sat 15-03-2025

Martinique, Caribbean

Disembark

Thu 27-03-2025

St Martin / St Maarten

From

€2900

Twister

Caribbean Island Hopping to MartiniqueTW060325

Embark

Thu 06-03-2025

St George’s, Grenada

Disembark

Fri 14-03-2025

Martinique, Caribbean

From

€2070

Twister

Suriname to the Spice Isle TW250225

Embark

Tue 25-02-2025

Paramaribo, Suriname, South America

Disembark

Wed 05-03-2025

St George’s, Grenada

From

€1710