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Windstar Cruises to Caribbean

Showing 126-133 of 133 results
49-Night Caribbean Cruise
$17,299
Windstar Cruises – Star Seeker
Departs Mar 27, 2026 from San Juan, Puerto Rico
Up to 3 deals including Avoya Exclusives
Roundtrip
7-Night Caribbean Cruise
$2,399
Windstar Cruises – Wind Surf
145 Reviews
Departs Mar 28, 2026 from Saint Maarten (Phillipsburg), Netherlands Antilles
Up to 3 deals including Avoya Exclusives
21-Night Caribbean Cruise
$3,999
Windstar Cruises – Wind Surf
145 Reviews
Departs Mar 28, 2026 from Saint Maarten (Phillipsburg), Netherlands Antilles
Up to 3 deals including Avoya Exclusives
7-Night Caribbean Cruise
$3,199
Windstar Cruises – Star Seeker
Departs Apr 06, 2026 from San Juan, Puerto Rico
Up to 3 deals including Avoya Exclusives
14-Night Caribbean Cruise
$5,599
Windstar Cruises – Star Seeker
Departs Apr 06, 2026 from San Juan, Puerto Rico
Up to 3 deals including Avoya Exclusives
22-Night Caribbean Cruise
$8,499
Windstar Cruises – Star Seeker
Departs Apr 06, 2026 from San Juan, Puerto Rico
Up to 3 deals including Avoya Exclusives
1-Night Caribbean Cruise
$299
Windstar Cruises – Star Seeker
Departs May 06, 2026 from Seattle, Washington
Up to 3 deals including Avoya Exclusives
Roundtrip
14-Night Caribbean Cruise
$6,499
Windstar Cruises – Wind Spirit
98 Reviews
Departs Feb 08, 2025 from Bridgetown, Barbados
Up to 3 deals including Avoya Exclusives
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