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Windstar Cruises to Caribbean

Showing 1-25 of 148 results
11-Night Caribbean Cruise
$3,399
Windstar Cruises – Star Pride
90 Reviews
Departs Oct 23, 2024 from Boston, Massachusetts
Roundtrip
6-Night Caribbean Cruise
$2,499
Windstar Cruises – Star Pride
90 Reviews
Departs Nov 03, 2024 from San Juan, Puerto Rico
Roundtrip
13-Night Caribbean Cruise
$5,049
Windstar Cruises – Star Pride
90 Reviews
Departs Nov 03, 2024 from San Juan, Puerto Rico
Roundtrip
7-Night Caribbean Cruise
$2,899
Windstar Cruises – Star Pride
90 Reviews
Departs Nov 09, 2024 from San Juan, Puerto Rico
Roundtrip
14-Night Caribbean Cruise
$4,299
Windstar Cruises – Star Pride
90 Reviews
Departs Nov 09, 2024 from San Juan, Puerto Rico
Roundtrip
7-Night Caribbean Cruise
$2,248
Windstar Cruises – Star Pride
90 Reviews
Departs Nov 16, 2024 from San Juan, Puerto Rico
Roundtrip
14-Night Caribbean Cruise
$3,778
Windstar Cruises – Star Pride
90 Reviews
Departs Nov 16, 2024 from San Juan, Puerto Rico
11-Night Caribbean Cruise
$3,418
Windstar Cruises – Wind Star
88 Reviews
Departs Nov 19, 2024 from Bridgetown, Barbados
Roundtrip
7-Night Caribbean Cruise
$2,248
Windstar Cruises – Star Pride
90 Reviews
Departs Nov 23, 2024 from San Juan, Puerto Rico
Roundtrip
14-Night Caribbean Cruise
$4,199
Windstar Cruises – Star Pride
90 Reviews
Departs Nov 23, 2024 from San Juan, Puerto Rico
Roundtrip
10-Night Caribbean Cruise
$3,699
Windstar Cruises – Wind Spirit
98 Reviews
Departs Nov 27, 2024 from Bridgetown, Barbados
Roundtrip
7-Night Caribbean Cruise
$2,699
Windstar Cruises – Star Pride
90 Reviews
Departs Nov 30, 2024 from San Juan, Puerto Rico
7-Night Caribbean Cruise
$2,123
Windstar Cruises – Star Pride
90 Reviews
Departs Dec 07, 2024 from San Juan, Puerto Rico
Up to 1 deal including an Avoya Exclusive
Roundtrip
7-Night Caribbean Cruise
$2,599
Windstar Cruises – Wind Spirit
98 Reviews
Departs Dec 07, 2024 from Bridgetown, Barbados
14-Night Caribbean Cruise
$3,999
Windstar Cruises – Star Pride
90 Reviews
Departs Dec 07, 2024 from San Juan, Puerto Rico
Roundtrip
14-Night Caribbean Cruise
$4,399
Windstar Cruises – Wind Spirit
98 Reviews
Departs Dec 07, 2024 from Bridgetown, Barbados
7-Night Caribbean Cruise
$2,123
Windstar Cruises – Star Pride
90 Reviews
Departs Dec 14, 2024 from Bridgetown, Barbados
Up to 1 deal including an Avoya Exclusive
Roundtrip
7-Night Caribbean Cruise
$2,699
Windstar Cruises – Wind Spirit
98 Reviews
Departs Dec 14, 2024 from Bridgetown, Barbados
Roundtrip
14-Night Caribbean Cruise
$4,599
Windstar Cruises – Wind Spirit
98 Reviews
Departs Dec 14, 2024 from Bridgetown, Barbados
Roundtrip
7-Night Caribbean Cruise
$2,899
Windstar Cruises – Wind Spirit
98 Reviews
Departs Dec 21, 2024 from Bridgetown, Barbados
Roundtrip
7-Night Caribbean Cruise
$2,999
Windstar Cruises – Wind Surf
145 Reviews
Departs Dec 21, 2024 from Saint Maarten (Phillipsburg), Netherlands Antilles
Roundtrip
14-Night Caribbean Cruise
$5,699
Windstar Cruises – Wind Spirit
98 Reviews
Departs Dec 21, 2024 from Bridgetown, Barbados
Roundtrip
14-Night Caribbean Cruise
$5,999
Windstar Cruises – Wind Surf
145 Reviews
Departs Dec 21, 2024 from Saint Maarten (Phillipsburg), Netherlands Antilles
Roundtrip
7-Night Caribbean Cruise
$3,399
Windstar Cruises – Wind Spirit
98 Reviews
Departs Dec 28, 2024 from Bridgetown, Barbados
Roundtrip
7-Night Caribbean Cruise
$4,299
Windstar Cruises – Wind Surf
145 Reviews
Departs Dec 28, 2024 from Saint Maarten (Phillipsburg), Netherlands Antilles
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