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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 Short Hop TW010326A

Embark

Sun 01-03-2026

Port of Spain, Trinidad

Disembark

Tue 03-03-2026

Martinique, Caribbean

From

€500

Twister

The Grenadines & Tobago Cays TW130226

Embark

Fri 13-02-2026

St George’s, Grenada

Disembark

Sun 22-02-2026

Port of Spain, Trinidad

From

€2490

Twister

Sail a Schooner Through the Grenadines TW030226

Embark

Tue 03-02-2026

Martinique, Caribbean

Disembark

Thu 12-02-2026

St George’s, Grenada

From

€2490