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Windstar Cruises to Caribbean

Showing 126-139 of 139 results
Roundtrip
14-Night Caribbean Cruise
$4,099
Windstar Cruises – Wind Spirit
98 Reviews
Departs Mar 14, 2026 from Bridgetown, Barbados
Up to 2 deals including an Avoya Exclusive
7-Night Caribbean Cruise
$3,199
Windstar Cruises – Star Pride
90 Reviews
Departs Mar 15, 2026 from Oranjestad, Aruba
Up to 2 deals including an Avoya Exclusive
Roundtrip
7-Night Caribbean Cruise
$2,299
Windstar Cruises – Wind Surf
145 Reviews
Departs Mar 21, 2026 from Saint Maarten (Phillipsburg), Netherlands Antilles
Up to 2 deals including an Avoya Exclusive
Roundtrip
7-Night Caribbean Cruise
$2,599
Windstar Cruises – Wind Spirit
98 Reviews
Departs Mar 21, 2026 from Bridgetown, Barbados
Up to 2 deals including an Avoya Exclusive
Roundtrip
14-Night Caribbean Cruise
$3,699
Windstar Cruises – Wind Surf
145 Reviews
Departs Mar 21, 2026 from Saint Maarten (Phillipsburg), Netherlands Antilles
Up to 2 deals including an Avoya Exclusive
Roundtrip
10-Night Caribbean Cruise
$3,999
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
$5,599
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
$8,099
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
$17,299
Windstar Cruises – Star Seeker
Departs Mar 27, 2026 from San Juan, Puerto Rico
Up to 2 deals including an Avoya Exclusive
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 2 deals including an Avoya Exclusive
1-Night Caribbean Cruise
$299
Windstar Cruises – Star Seeker
Departs May 06, 2026 from Seattle, Washington
Up to 2 deals including an Avoya Exclusive
Roundtrip
14-Night Caribbean Cruise
$5,299
Windstar Cruises – Wind Spirit
98 Reviews
Departs Dec 21, 2024 from Bridgetown, Barbados
Roundtrip
7-Night Caribbean Cruise
$3,799
Windstar Cruises – Wind Spirit
98 Reviews
Departs Dec 28, 2024 from Bridgetown, Barbados
Up to 2 deals including an Avoya Exclusive
Roundtrip
14-Night Caribbean Cruise
$5,199
Windstar Cruises – Wind Spirit
98 Reviews
Departs Dec 28, 2024 from Bridgetown, Barbados
Up to 2 deals including an Avoya Exclusive
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