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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

Tenacious

Tenacious Atlantic Sailing Holiday from Bermuda to Portland UK TNS625

Embark

Sat 01-04-2023

St Georges, Bermuda

Disembark

Sun 30-04-2023

Portland, UK

Sailing holidays on Tall ship Tenacious

From

£1705.00

Tenacious

Tenacious Caribbean Sailing Holiday from Antigua to Bermuda TNS624

Embark

Mon 13-03-2023

Antigua, Caribbean

Disembark

Mon 27-03-2023

St Georges, Bermuda

Sailing holidays on Tenacious with Classic Sailing

From

£895.00

Tenacious

Tenacious Caribbean Sailing Holiday from Antigua TNS622

Embark

Tue 14-02-2023

Antigua, Caribbean

Disembark

Mon 27-02-2023

Antigua, Caribbean

Sailing holidays on Tenacious with Classic Sailing

From

£1495.00