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Windstar Cruises to Caribbean

Showing 76-100 of 133 results
Roundtrip
55-Night Caribbean Cruise
$17,899
Windstar Cruises – Wind Surf
145 Reviews
Departs Jan 04, 2026 from Saint Maarten (Phillipsburg), Netherlands Antilles
Up to 3 deals including Avoya Exclusives
7-Night Caribbean Cruise
$2,599
Windstar Cruises – Wind Surf
145 Reviews
Departs Jan 11, 2026 from Saint Maarten (Phillipsburg), Netherlands Antilles
Up to 3 deals including Avoya Exclusives
14-Night Caribbean Cruise
$4,199
Windstar Cruises – Wind Surf
145 Reviews
Departs Jan 11, 2026 from Saint Maarten (Phillipsburg), Netherlands Antilles
Up to 3 deals including Avoya Exclusives
8-Night Caribbean Cruise
$5,399
Windstar Cruises – Star Seeker
Departs Jan 15, 2026 from Miami, Florida
Up to 3 deals including Avoya Exclusives
Roundtrip
7-Night Caribbean Cruise
$2,699
Windstar Cruises – Wind Surf
145 Reviews
Departs Jan 18, 2026 from Bridgetown, Barbados
Up to 3 deals including Avoya Exclusives
14-Night Caribbean Cruise
$4,599
Windstar Cruises – Wind Surf
145 Reviews
Departs Jan 18, 2026 from Bridgetown, Barbados
Up to 3 deals including Avoya Exclusives
Roundtrip
7-Night Caribbean Cruise
$3,299
Windstar Cruises – Star Seeker
Departs Jan 23, 2026 from San Juan, Puerto Rico
Up to 3 deals including Avoya Exclusives
Roundtrip
14-Night Caribbean Cruise
$5,599
Windstar Cruises – Star Seeker
Departs Jan 23, 2026 from San Juan, Puerto Rico
Up to 3 deals including Avoya Exclusives
Roundtrip
7-Night Caribbean Cruise
$2,599
Windstar Cruises – Wind Spirit
98 Reviews
Departs Jan 24, 2026 from Saint Maarten (Phillipsburg), Netherlands Antilles
Up to 3 deals including Avoya Exclusives
7-Night Caribbean Cruise
$2,799
Windstar Cruises – Wind Surf
145 Reviews
Departs Jan 25, 2026 from Bridgetown, Barbados
Up to 3 deals including Avoya Exclusives
15-Night Caribbean Cruise
$4,999
Windstar Cruises – Wind Surf
145 Reviews
Departs Jan 25, 2026 from Bridgetown, Barbados
Up to 3 deals including Avoya Exclusives
Roundtrip
7-Night Caribbean Cruise
$3,299
Windstar Cruises – Star Seeker
Departs Jan 30, 2026 from San Juan, Puerto Rico
Up to 3 deals including Avoya Exclusives
Roundtrip
14-Night Caribbean Cruise
$5,299
Windstar Cruises – Star Seeker
Departs Jan 30, 2026 from San Juan, Puerto Rico
Up to 3 deals including Avoya Exclusives
Roundtrip
14-Night Caribbean Cruise
$4,099
Windstar Cruises – Wind Spirit
98 Reviews
Departs Jan 31, 2026 from Saint Maarten (Phillipsburg), Netherlands Antilles
Up to 3 deals including Avoya Exclusives
Roundtrip
7-Night Caribbean Cruise
$2,999
Windstar Cruises – Star Seeker
Departs Feb 06, 2026 from San Juan, Puerto Rico
Up to 3 deals including Avoya Exclusives
Roundtrip
14-Night Caribbean Cruise
$5,299
Windstar Cruises – Star Seeker
Departs Feb 06, 2026 from San Juan, Puerto Rico
Up to 3 deals including Avoya Exclusives
Roundtrip
14-Night Caribbean Cruise
$4,099
Windstar Cruises – Wind Spirit
98 Reviews
Departs Feb 07, 2026 from Saint Maarten (Phillipsburg), Netherlands Antilles
Up to 3 deals including Avoya Exclusives
Roundtrip
7-Night Caribbean Cruise
$3,299
Windstar Cruises – Star Seeker
Departs Feb 13, 2026 from San Juan, Puerto Rico
Up to 3 deals including Avoya Exclusives
Roundtrip
14-Night Caribbean Cruise
$5,399
Windstar Cruises – Star Seeker
Departs Feb 13, 2026 from San Juan, Puerto Rico
Up to 3 deals including Avoya Exclusives
Roundtrip
7-Night Caribbean Cruise
$2,599
Windstar Cruises – Wind Spirit
98 Reviews
Departs Feb 14, 2026 from Saint Maarten (Phillipsburg), Netherlands Antilles
Up to 3 deals including Avoya Exclusives
11-Night Caribbean Cruise
$3,999
Windstar Cruises – Wind Surf
145 Reviews
Departs Feb 17, 2026 from Cozumel, Mexico
Up to 3 deals including Avoya Exclusives
18-Night Caribbean Cruise
$5,399
Windstar Cruises – Wind Surf
145 Reviews
Departs Feb 17, 2026 from Cozumel, Mexico
Up to 3 deals including Avoya Exclusives
Roundtrip
7-Night Caribbean Cruise
$3,099
Windstar Cruises – Star Seeker
Departs Feb 20, 2026 from San Juan, Puerto Rico
Up to 3 deals including Avoya Exclusives
Roundtrip
14-Night Caribbean Cruise
$5,199
Windstar Cruises – Star Seeker
Departs Feb 20, 2026 from San Juan, Puerto Rico
Up to 3 deals including Avoya Exclusives
Roundtrip
7-Night Caribbean Cruise
$2,599
Windstar Cruises – Wind Spirit
98 Reviews
Departs Feb 21, 2026 from Saint Maarten (Phillipsburg), Netherlands Antilles
Up to 3 deals including Avoya Exclusives
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