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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


The Caribbean Sailing Voyages

Eye of the Wind

Caribbean Christmas 2023 EYE23/42


Fri 22-12-2023

Bridgetown, Barbados


Fri 29-12-2023

St George’s, Grenada

Limited Spaces Available Caribbean Sunset - The Caribbean on a Tall Ship Sailing Morgenster with Classic Sailing




Tenacious Atlantic Sailing Holiday from Bermuda to Portland UK TNS625


Sat 01-04-2023

St Georges, Bermuda


Sun 30-04-2023

Portland, UK

Sailing holidays on Tall ship Tenacious