More

Voyage Filters

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

,

The Caribbean Sailing Voyages

Eye of the Wind

Ocean Passage from the Caribbean to Bermuda- EYE25/07

Embark

Tue 18-02-2025

Marigot, St Martin

Disembark

Sat 01-03-2025

St Georges, Bermuda

Sailing holidays on the Eye of the Wind

From

€3850

Eye of the Wind

Hidden Gems of the Caribbean- EYE25/05

Embark

Fri 31-01-2025

Anse Mitan, Martinique

Disembark

Fri 07-02-2025

Pointe a Pitre, Guadeloupe

From

€2590

Eye of the Wind

Explore the Caribbean Sea- EYE25/04

Embark

Fri 24-01-2025

Le Marin, Martinique

Disembark

Fri 31-01-2025

Anse Mitan, Martinique

From

€2590