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Windstar Cruises to Caribbean

Showing 1-25 of 124 results
7-night caribbean cruise
Oceanview From
$2,443
Windstar Cruises – Star Pride
4.595 Reviews
Departs Nov 15, 2026 from San Juan, Puerto Rico
Up to 2 deals including an Avoya Exclusive
View Expanded Details
14-night caribbean cruise
Oceanview From
$4,644
Windstar Cruises – Star Pride
4.595 Reviews
Departs Nov 15, 2026 from San Juan, Puerto Rico
Up to 2 deals including an Avoya Exclusive
View Expanded Details
7-night caribbean cruise
Oceanview From
$2,411
Windstar Cruises – Star Pride
4.595 Reviews
Departs Nov 22, 2026 from San Juan, Puerto Rico
Up to 2 deals including an Avoya Exclusive
View Expanded Details
14-night caribbean cruise
Oceanview From
$5,974
Windstar Cruises – Star Pride
4.595 Reviews
Departs Nov 22, 2026 from San Juan, Puerto Rico
Up to 2 deals including an Avoya Exclusive
View Expanded Details
11-night caribbean cruise
Oceanview From
$5,036
Windstar Cruises – Wind Star
4.689 Reviews
Departs Nov 24, 2026 from Bridgetown, Barbados
Up to 2 deals including an Avoya Exclusive
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18-night caribbean cruise
Oceanview From
$8,141
Windstar Cruises – Wind Star
4.689 Reviews
Departs Nov 24, 2026 from Bridgetown, Barbados
Up to 1 deal including an Avoya Exclusive
View Expanded Details
7-night caribbean cruise
Oceanview From
$2,419
Windstar Cruises – Star Legend
4.586 Reviews
Departs Nov 27, 2026 from Bridgetown, Barbados
Up to 2 deals including an Avoya Exclusive
View Expanded Details
15-night caribbean cruise
Oceanview From
$4,709
Windstar Cruises – Star Legend
4.586 Reviews
Departs Nov 27, 2026 from Bridgetown, Barbados
Up to 2 deals including an Avoya Exclusive
View Expanded Details
7-night caribbean cruise
Oceanview From
$3,843
Windstar Cruises – Star Pride
4.595 Reviews
Departs Nov 29, 2026 from San Juan, Puerto Rico
Up to 2 deals including an Avoya Exclusive
View Expanded Details
14-night caribbean cruise
Oceanview From
$5,974
Windstar Cruises – Star Pride
4.595 Reviews
Departs Nov 29, 2026 from San Juan, Puerto Rico
Up to 2 deals including an Avoya Exclusive
View Expanded Details
8-night caribbean cruise
Oceanview From
$2,740
Windstar Cruises – Star Legend
4.586 Reviews
Departs Dec 04, 2026 from Bridgetown, Barbados
Up to 2 deals including an Avoya Exclusive
View Expanded Details
16-night caribbean cruise
Oceanview From
$5,182
Windstar Cruises – Star Legend
4.586 Reviews
Departs Dec 04, 2026 from Bridgetown, Barbados
Up to 2 deals including an Avoya Exclusive
View Expanded Details
7-night caribbean cruise
Oceanview From
$2,411
Windstar Cruises – Star Pride
4.595 Reviews
Departs Dec 06, 2026 from San Juan, Puerto Rico
Up to 2 deals including an Avoya Exclusive
View Expanded Details
14-night caribbean cruise
Oceanview From
$4,434
Windstar Cruises – Star Pride
4.595 Reviews
Departs Dec 06, 2026 from San Juan, Puerto Rico
Up to 2 deals including an Avoya Exclusive
View Expanded Details
7-night caribbean cruise
Oceanview From
$2,443
Windstar Cruises – Star Pride
4.595 Reviews
Departs Dec 13, 2026 from San Juan, Puerto Rico
Up to 2 deals including an Avoya Exclusive
View Expanded Details
14-night caribbean cruise
Oceanview From
$4,644
Windstar Cruises – Star Pride
4.595 Reviews
Departs Dec 13, 2026 from San Juan, Puerto Rico
Up to 2 deals including an Avoya Exclusive
View Expanded Details
7-night caribbean cruise
Oceanview From
$2,658
Windstar Cruises – Wind Surf
4.7148 Reviews
Departs Dec 19, 2026 from Saint Maarten (Phillipsburg), Netherlands Antilles
Up to 2 deals including an Avoya Exclusive
View Expanded Details
14-night caribbean cruise
Oceanview From
$6,560
Windstar Cruises – Wind Surf
4.7148 Reviews
Departs Dec 19, 2026 from Saint Maarten (Phillipsburg), Netherlands Antilles
Up to 2 deals including an Avoya Exclusive
View Expanded Details
7-night caribbean cruise
Inside From
$2,411
Windstar Cruises – Star Pride
4.595 Reviews
Departs Dec 20, 2026 from San Juan, Puerto Rico
Up to 2 deals including an Avoya Exclusive
View Expanded Details
14-night caribbean cruise
Oceanview From
$4,644
Windstar Cruises – Star Pride
4.595 Reviews
Departs Dec 20, 2026 from San Juan, Puerto Rico
Up to 2 deals including an Avoya Exclusive
View Expanded Details
7-night caribbean cruise
Oceanview From
$4,182
Windstar Cruises – Wind Surf
4.7148 Reviews
Departs Dec 26, 2026 from Saint Maarten (Phillipsburg), Netherlands Antilles
Up to 2 deals including an Avoya Exclusive
View Expanded Details
14-night caribbean cruise
Oceanview From
$6,560
Windstar Cruises – Wind Surf
4.7148 Reviews
Departs Dec 26, 2026 from Saint Maarten (Phillipsburg), Netherlands Antilles
Up to 2 deals including an Avoya Exclusive
View Expanded Details
7-night caribbean cruise
Oceanview From
$2,443
Windstar Cruises – Star Pride
4.595 Reviews
Departs Dec 27, 2026 from San Juan, Puerto Rico
Up to 2 deals including an Avoya Exclusive
View Expanded Details
14-night caribbean cruise
Oceanview From
$5,414
Windstar Cruises – Star Pride
4.595 Reviews
Departs Dec 27, 2026 from San Juan, Puerto Rico
Up to 2 deals including an Avoya Exclusive
View Expanded Details
7-night caribbean cruise
Oceanview From
$2,658
Windstar Cruises – Wind Surf
4.7148 Reviews
Departs Jan 02, 2027 from Saint Maarten (Phillipsburg), Netherlands Antilles
Up to 2 deals including an Avoya Exclusive
View Expanded Details
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