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Windstar Cruises to Caribbean

Showing 51-75 of 124 results
7-night caribbean cruise
$3,299
Windstar Cruises – Wind Surf
4.7 (148)
Departs Mar 14, 2026 from Saint Maarten (Phillipsburg), Netherlands Antilles
Up to 1 deal
14-night caribbean cruise
$5,599
Windstar Cruises – Wind Surf
4.7 (148)
Departs Mar 14, 2026 from Saint Maarten (Phillipsburg), Netherlands Antilles
Up to 2 deals including an Avoya Exclusive
7-night caribbean cruise
$2,799
Windstar Cruises – Star Pride
4.5 (95)
Departs Mar 15, 2026 from Oranjestad, Aruba
Up to 2 deals including an Avoya Exclusive
6-night caribbean cruise
$3,499
Windstar Cruises – Wind Spirit
4.8 (100)
Departs Mar 15, 2026 from Bridgetown, Barbados
Up to 1 deal
7-night caribbean cruise
$3,099
Windstar Cruises – Wind Spirit
4.8 (100)
Departs Mar 21, 2026 from Bridgetown, Barbados
Up to 2 deals including an Avoya Exclusive
7-night caribbean cruise
$3,399
Windstar Cruises – Wind Surf
4.7 (147)
Departs Mar 21, 2026 from Saint Maarten (Phillipsburg), Netherlands Antilles
Up to 2 deals including an Avoya Exclusive
14-night caribbean cruise
$5,899
Windstar Cruises – Wind Surf
4.7 (148)
Departs Mar 21, 2026 from Saint Maarten (Phillipsburg), Netherlands Antilles
Up to 2 deals including an Avoya Exclusive
10-night caribbean cruise
$5,799
Windstar Cruises – Star Seeker
Departs Mar 27, 2026 from San Juan, Puerto Rico
Up to 2 deals including an Avoya Exclusive
17-night caribbean cruise
$8,499
Windstar Cruises – Star Seeker
Departs Mar 27, 2026 from San Juan, Puerto Rico
Up to 2 deals including an Avoya Exclusive
24-night caribbean cruise
$14,299
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
$29,399
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
$3,499
Windstar Cruises – Wind Surf
4.7 (148)
Departs Mar 28, 2026 from Saint Maarten (Phillipsburg), Netherlands Antilles
Up to 2 deals including an Avoya Exclusive
21-night caribbean cruise
$5,299
Windstar Cruises – Wind Surf
4.7 (148)
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 (95)
Departs Oct 20, 2026 from Boston, Massachusetts
Up to 2 deals including an Avoya Exclusive
11-night caribbean cruise
$3,599
Windstar Cruises – Star Pride
4.5 (95)
Departs Oct 28, 2026 from San Juan, Puerto Rico
Up to 2 deals including an Avoya Exclusive
7-night caribbean cruise
$2,499
Windstar Cruises – Star Pride
4.5 (95)
Departs Nov 08, 2026 from San Juan, Puerto Rico
Up to 2 deals including an Avoya Exclusive
14-night caribbean cruise
$3,999
Windstar Cruises – Star Pride
4.5 (95)
Departs Nov 08, 2026 from San Juan, Puerto Rico
Up to 2 deals including an Avoya Exclusive
7-night caribbean cruise
$2,499
Windstar Cruises – Star Pride
4.5 (95)
Departs Nov 15, 2026 from San Juan, Puerto Rico
Up to 2 deals including an Avoya Exclusive
14-night caribbean cruise
$4,099
Windstar Cruises – Star Pride
4.5 (95)
Departs Nov 15, 2026 from San Juan, Puerto Rico
Up to 2 deals including an Avoya Exclusive
7-night caribbean cruise
$2,699
Windstar Cruises – Star Pride
4.5 (95)
Departs Nov 22, 2026 from San Juan, Puerto Rico
Up to 2 deals including an Avoya Exclusive
14-night caribbean cruise
$4,099
Windstar Cruises – Star Pride
4.5 (95)
Departs Nov 22, 2026 from San Juan, Puerto Rico
Up to 2 deals including an Avoya Exclusive
11-night caribbean cruise
$4,299
Windstar Cruises – Wind Star
4.6 (89)
Departs Nov 24, 2026 from Bridgetown, Barbados
Up to 2 deals including an Avoya Exclusive
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