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Windstar Cruises to Caribbean

Showing 51-75 of 106 results
28-night caribbean cruise
$8,299
Windstar Cruises – Wind Spirit
4.8 (98)
Departs Feb 21, 2026 from Saint Maarten (Phillipsburg), Netherlands Antilles
14-night caribbean cruise
$14,899
Windstar Cruises – Star Seeker
Departs Feb 27, 2026 from San Juan, Puerto Rico
Up to 2 deals including an Avoya Exclusive
7-night caribbean cruise
$2,499
Windstar Cruises – Wind Spirit
4.8 (98)
Departs Feb 28, 2026 from Saint Maarten (Phillipsburg), Netherlands Antilles
Up to 2 deals including an Avoya Exclusive
7-night caribbean cruise
$2,599
Windstar Cruises – Wind Surf
4.7 (146)
Departs Feb 28, 2026 from Saint Maarten (Phillipsburg), Netherlands Antilles
Up to 2 deals including an Avoya Exclusive
15-night caribbean cruise
$3,999
Windstar Cruises – Wind Spirit
4.8 (98)
Departs Feb 28, 2026 from Saint Maarten (Phillipsburg), Netherlands Antilles
Up to 1 deal including an Avoya Exclusive
14-night caribbean cruise
$4,499
Windstar Cruises – Wind Surf
4.7 (146)
Departs Feb 28, 2026 from Saint Maarten (Phillipsburg), Netherlands Antilles
Up to 2 deals including an Avoya Exclusive
7-night caribbean cruise
$5,199
Windstar Cruises – Star Seeker
Departs Mar 06, 2026 from San Juan, Puerto Rico
Up to 2 deals including an Avoya Exclusive
14-night caribbean cruise
$13,699
Windstar Cruises – Star Seeker
Departs Mar 06, 2026 from San Juan, Puerto Rico
Up to 2 deals including an Avoya Exclusive
14-night caribbean cruise
$4,099
Windstar Cruises – Wind Spirit
4.8 (98)
Departs Mar 07, 2026 from Bridgetown, Barbados
Up to 2 deals including an Avoya Exclusive
14-night caribbean cruise
$3,999
Windstar Cruises – Wind Surf
4.7 (146)
Departs Mar 14, 2026 from Saint Maarten (Phillipsburg), Netherlands Antilles
Up to 2 deals including an Avoya Exclusive
7-night caribbean cruise
$2,599
Windstar Cruises – Star Pride
4.5 (93)
Departs Mar 15, 2026 from Oranjestad, Aruba
Up to 2 deals including an Avoya Exclusive
7-night caribbean cruise
$2,399
Windstar Cruises – Wind Surf
4.7 (146)
Departs Mar 21, 2026 from Saint Maarten (Phillipsburg), Netherlands Antilles
Up to 2 deals including an Avoya Exclusive
7-night caribbean cruise
$2,599
Windstar Cruises – Wind Spirit
4.8 (98)
Departs Mar 21, 2026 from Bridgetown, Barbados
Up to 2 deals including an Avoya Exclusive
14-night caribbean cruise
$3,699
Windstar Cruises – Wind Surf
4.7 (146)
Departs Mar 21, 2026 from Saint Maarten (Phillipsburg), Netherlands Antilles
Up to 2 deals including an Avoya Exclusive
6-night caribbean cruise
$2,399
Windstar Cruises – Wind Surf
4.7 (146)
Departs Mar 28, 2026 from Saint Maarten (Phillipsburg), Netherlands Antilles
Up to 2 deals including an Avoya Exclusive
14-night caribbean cruise
$5,699
Windstar Cruises – Star Seeker
Departs Apr 06, 2026 from San Juan, Puerto Rico
Up to 2 deals including an Avoya Exclusive
8-night caribbean cruise
$2,399
Windstar Cruises – Star Pride
4.5 (93)
Departs Oct 20, 2026 from Boston, Massachusetts
Up to 1 deal including an Avoya Exclusive
11-night caribbean cruise
$3,599
Windstar Cruises – Star Pride
4.5 (91)
Departs Oct 28, 2026 from San Juan, Puerto Rico
Up to 1 deal including an Avoya Exclusive
7-night caribbean cruise
$2,499
Windstar Cruises – Star Pride
4.5 (91)
Departs Nov 08, 2026 from San Juan, Puerto Rico
Up to 1 deal including an Avoya Exclusive
14-night caribbean cruise
$3,999
Windstar Cruises – Star Pride
4.5 (92)
Departs Nov 08, 2026 from San Juan, Puerto Rico
Up to 1 deal including an Avoya Exclusive
7-night caribbean cruise
$2,499
Windstar Cruises – Star Pride
4.5 (91)
Departs Nov 15, 2026 from San Juan, Puerto Rico
Up to 1 deal including an Avoya Exclusive
14-night caribbean cruise
$3,999
Windstar Cruises – Star Pride
4.5 (91)
Departs Nov 15, 2026 from San Juan, Puerto Rico
Up to 1 deal including an Avoya Exclusive
7-night caribbean cruise
$2,499
Windstar Cruises – Star Pride
4.5 (91)
Departs Nov 22, 2026 from San Juan, Puerto Rico
Up to 1 deal including an Avoya Exclusive
14-night caribbean cruise
$3,999
Windstar Cruises – Star Pride
4.5 (91)
Departs Nov 22, 2026 from San Juan, Puerto Rico
Up to 1 deal including an Avoya Exclusive
11-night caribbean cruise
$3,799
Windstar Cruises – Wind Star
4.6 (89)
Departs Nov 24, 2026 from Bridgetown, Barbados
Up to 1 deal including an Avoya Exclusive
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