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Windstar Cruises to Caribbean

Showing 26-50 of 106 results
55-night caribbean cruise
$19,299
Windstar Cruises – Wind Surf
4.7 (146)
Departs Jan 04, 2026 from Saint Maarten (Phillipsburg), Netherlands Antilles
Up to 2 deals including an Avoya Exclusive
7-night caribbean cruise
$2,699
Windstar Cruises – Wind Surf
4.7 (146)
Departs Jan 11, 2026 from Saint Maarten (Phillipsburg), Netherlands Antilles
Up to 1 deal
14-night caribbean cruise
$4,299
Windstar Cruises – Wind Surf
4.7 (146)
Departs Jan 11, 2026 from Saint Maarten (Phillipsburg), Netherlands Antilles
Up to 1 deal
10-night caribbean cruise
$4,599
Windstar Cruises – Wind Spirit
4.8 (98)
Departs Jan 14, 2026 from Saint Maarten (Phillipsburg), Netherlands Antilles
Up to 2 deals including an Avoya Exclusive
17-night caribbean cruise
$6,699
Windstar Cruises – Wind Spirit
4.8 (98)
Departs Jan 14, 2026 from Saint Maarten (Phillipsburg), Netherlands Antilles
Up to 2 deals including an Avoya Exclusive
8-night caribbean cruise
$5,849
Windstar Cruises – Star Seeker
Departs Jan 15, 2026 from Miami, Florida
Up to 1 deal
7-night caribbean cruise
$2,699
Windstar Cruises – Wind Surf
4.7 (146)
Departs Jan 18, 2026 from Bridgetown, Barbados
Up to 1 deal
14-night caribbean cruise
$4,899
Windstar Cruises – Wind Surf
4.7 (146)
Departs Jan 18, 2026 from Bridgetown, Barbados
Up to 2 deals including an Avoya Exclusive
7-night caribbean cruise
$3,799
Windstar Cruises – Star Seeker
Departs Jan 23, 2026 from San Juan, Puerto Rico
Up to 2 deals including an Avoya Exclusive
14-night caribbean cruise
$6,499
Windstar Cruises – Star Seeker
Departs Jan 23, 2026 from San Juan, Puerto Rico
Up to 2 deals including an Avoya Exclusive
7-night caribbean cruise
$2,699
Windstar Cruises – Wind Spirit
4.8 (98)
Departs Jan 24, 2026 from Saint Maarten (Phillipsburg), Netherlands Antilles
Up to 2 deals including an Avoya Exclusive
7-night caribbean cruise
$2,999
Windstar Cruises – Wind Surf
4.7 (146)
Departs Jan 25, 2026 from Bridgetown, Barbados
Up to 2 deals including an Avoya Exclusive
15-night caribbean cruise
$5,299
Windstar Cruises – Wind Surf
4.7 (146)
Departs Jan 25, 2026 from Bridgetown, Barbados
Up to 2 deals including an Avoya Exclusive
7-night caribbean cruise
$3,499
Windstar Cruises – Star Seeker
Departs Jan 30, 2026 from San Juan, Puerto Rico
Up to 2 deals including an Avoya Exclusive
14-night caribbean cruise
$8,059
Windstar Cruises – Star Seeker
Departs Jan 30, 2026 from San Juan, Puerto Rico
Up to 2 deals including an Avoya Exclusive
6-night caribbean cruise
$2,499
Windstar Cruises – Wind Spirit
4.8 (98)
Departs Jan 31, 2026 from Saint Maarten (Phillipsburg), Netherlands Antilles
Up to 2 deals including an Avoya Exclusive
14-night caribbean cruise
$4,699
Windstar Cruises – Wind Spirit
4.8 (98)
Departs Jan 31, 2026 from Saint Maarten (Phillipsburg), Netherlands Antilles
Up to 2 deals including an Avoya Exclusive
7-night caribbean cruise
$2,899
Windstar Cruises – Wind Spirit
4.8 (98)
Departs Feb 07, 2026 from Saint Maarten (Phillipsburg), Netherlands Antilles
Up to 2 deals including an Avoya Exclusive
14-night caribbean cruise
$4,799
Windstar Cruises – Wind Spirit
4.8 (98)
Departs Feb 07, 2026 from Saint Maarten (Phillipsburg), Netherlands Antilles
Up to 2 deals including an Avoya Exclusive
6-night caribbean cruise
$2,599
Windstar Cruises – Wind Spirit
4.8 (98)
Departs Feb 14, 2026 from Saint Maarten (Phillipsburg), Netherlands Antilles
Up to 2 deals including an Avoya Exclusive
11-night caribbean cruise
$3,999
Windstar Cruises – Wind Surf
4.7 (146)
Departs Feb 17, 2026 from Cozumel, Mexico
Up to 2 deals including an Avoya Exclusive
18-night caribbean cruise
$5,599
Windstar Cruises – Wind Surf
4.7 (146)
Departs Feb 17, 2026 from Cozumel, Mexico
Up to 2 deals including an Avoya Exclusive
14-night caribbean cruise
$5,699
Windstar Cruises – Star Seeker
Departs Feb 20, 2026 from San Juan, Puerto Rico
Up to 2 deals including an Avoya Exclusive
6-night caribbean cruise
$2,599
Windstar Cruises – Wind Spirit
4.8 (98)
Departs Feb 21, 2026 from Saint Maarten (Phillipsburg), Netherlands Antilles
Up to 2 deals including an Avoya Exclusive
14-night caribbean cruise
$4,099
Windstar Cruises – Wind Spirit
4.8 (98)
Departs Feb 21, 2026 from Saint Maarten (Phillipsburg), Netherlands Antilles
Up to 2 deals including an Avoya Exclusive
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