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Windstar Cruises to Caribbean

Showing 76-100 of 136 results
24-night caribbean cruise
$14,889
Windstar Cruises – Star Seeker
Departs Mar 27, 2026 from San Juan, Puerto Rico
Up to 2 deals including an Avoya Exclusive
49-night caribbean cruise
$30,849
Windstar Cruises – Star Seeker
Departs Mar 27, 2026 from San Juan, Puerto Rico
Up to 2 deals including an Avoya Exclusive
7-night caribbean cruise
$2,699
Windstar Cruises – Wind Surf
4.7 (147)
Departs Mar 28, 2026 from Saint Maarten (Phillipsburg), Netherlands Antilles
Up to 2 deals including an Avoya Exclusive
21-night caribbean cruise
$4,499
Windstar Cruises – Wind Surf
4.7 (147)
Departs Mar 28, 2026 from Saint Maarten (Phillipsburg), Netherlands Antilles
Up to 2 deals including an Avoya Exclusive
7-night caribbean cruise
$3,699
Windstar Cruises – Star Seeker
Departs Apr 06, 2026 from San Juan, Puerto Rico
Up to 2 deals including an Avoya Exclusive
14-night caribbean cruise
$6,299
Windstar Cruises – Star Seeker
Departs Apr 06, 2026 from San Juan, Puerto Rico
Up to 2 deals including an Avoya Exclusive
22-night caribbean cruise
$9,599
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
11-night caribbean cruise
$3,599
Windstar Cruises – Star Pride
4.5 (93)
Departs Oct 28, 2026 from San Juan, Puerto Rico
Up to 1 deal
7-night caribbean cruise
$2,499
Windstar Cruises – Star Pride
4.5 (93)
Departs Nov 08, 2026 from San Juan, Puerto Rico
Up to 1 deal
14-night caribbean cruise
$3,999
Windstar Cruises – Star Pride
4.5 (93)
Departs Nov 08, 2026 from San Juan, Puerto Rico
Up to 1 deal
7-night caribbean cruise
$2,499
Windstar Cruises – Star Pride
4.5 (93)
Departs Nov 15, 2026 from San Juan, Puerto Rico
Up to 1 deal
14-night caribbean cruise
$3,999
Windstar Cruises – Star Pride
4.5 (93)
Departs Nov 15, 2026 from San Juan, Puerto Rico
Up to 1 deal
7-night caribbean cruise
$2,499
Windstar Cruises – Star Pride
4.5 (93)
Departs Nov 22, 2026 from San Juan, Puerto Rico
Up to 1 deal
14-night caribbean cruise
$3,999
Windstar Cruises – Star Pride
4.5 (93)
Departs Nov 22, 2026 from San Juan, Puerto Rico
Up to 1 deal
11-night caribbean cruise
$4,099
Windstar Cruises – Wind Star
4.6 (89)
Departs Nov 24, 2026 from Bridgetown, Barbados
Up to 1 deal
18-night caribbean cruise
$6,899
Windstar Cruises – Wind Star
4.6 (89)
Departs Nov 24, 2026 from Bridgetown, Barbados
Up to 1 deal
15-night caribbean cruise
$4,099
Windstar Cruises – Star Legend
4.5 (86)
Departs Nov 27, 2026 from Bridgetown, Barbados
7-night caribbean cruise
$2,499
Windstar Cruises – Star Pride
4.5 (93)
Departs Nov 29, 2026 from San Juan, Puerto Rico
Up to 1 deal
14-night caribbean cruise
$3,999
Windstar Cruises – Star Pride
4.5 (93)
Departs Nov 29, 2026 from San Juan, Puerto Rico
Up to 1 deal
8-night caribbean cruise
$2,999
Windstar Cruises – Star Legend
4.5 (86)
Departs Dec 04, 2026 from Bridgetown, Barbados
16-night caribbean cruise
$4,099
Windstar Cruises – Star Legend
4.5 (86)
Departs Dec 04, 2026 from Bridgetown, Barbados
7-night caribbean cruise
$2,499
Windstar Cruises – Star Pride
4.5 (93)
Departs Dec 06, 2026 from San Juan, Puerto Rico
Up to 1 deal
14-night caribbean cruise
$3,999
Windstar Cruises – Star Pride
4.5 (93)
Departs Dec 06, 2026 from San Juan, Puerto Rico
Up to 1 deal
7-night caribbean cruise
$2,499
Windstar Cruises – Star Pride
4.5 (93)
Departs Dec 13, 2026 from San Juan, Puerto Rico
Up to 1 deal
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