The Caribbean Season extends from mid-December to the end of April normally culminating with Antigua Classics.
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
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.
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Caribbean Short Hop TW010326A
Embark
Sun 01-03-2026
Port of Spain, Trinidad
Disembark
Tue 03-03-2026
Martinique, Caribbean
From
€500
The Grenadines & Tobago Cays TW130226
Embark
Fri 13-02-2026
St George’s, Grenada
Disembark
Sun 22-02-2026
Port of Spain, Trinidad
From
€2490
Sail a Schooner Through the Grenadines TW030226
Embark
Tue 03-02-2026
Martinique, Caribbean
Disembark
Thu 12-02-2026
St George’s, Grenada
From
€2490