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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

Eye of the Wind

Explore the British Virgin Islands by Tall Ship EYE23/08

Embark

Fri 17-02-2023

Tortola, Caribbean

Disembark

Fri 24-02-2023

Tortola, Caribbean

Limited Spaces Available Sailing holidays in the Caribbean with Classic Sailing

From

€2390.00

Morgenster

Caribbean Island Hopping MR050124

Embark

Fri 05-01-2024

Pointe a Pitre, Guadeloupe

Disembark

Thu 11-01-2024

St Martin / St Maarten

Sail in the Caribbean with Classic Sailing

From

€1680

Morgenster

A Colourful Caribbean New Year MR291223

Embark

Fri 29-12-2023

Martinique, Caribbean

Disembark

Thu 04-01-2024

Pointe a Pitre, Guadeloupe

Caribbean Beach - The Caribbean on a Tall Ship Sailing Morgenster with Classic Sailing

From

€1880