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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

Grayhound

Caribbean - St Lucia to Guadeloupe GR060324

Embark

Wed 28-02-2024

Rodney Bay, Saint Lucia

Disembark

Mon 04-03-2024

Pointe a Pitre, Guadeloupe

Grayhound Sailing

From

€1610.00

Eye of the Wind

100% Caribbean - Eye of the Wind - EYE24/03

Embark

Fri 12-01-2024

Martinique, Caribbean

Disembark

Fri 19-01-2024

Martinique, Caribbean

sailing in the Caribbean with classic sailing

From

€2390

Grayhound

St Lucia Round trip GR280224

Embark

Wed 28-02-2024

Rodney Bay, Saint Lucia

Disembark

Mon 04-03-2024

Rodney Bay, Saint Lucia

Grayhound with Classic Sailing

From

€1380.00