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Windstar Cruises to Caribbean

Showing 1-25 of 133 results
Roundtrip
10-Night Caribbean Cruise
$3,999
Windstar Cruises – Wind Spirit
98 Reviews
Departs Nov 27, 2024 from Bridgetown, Barbados
Up to 3 deals including Avoya Exclusives
Roundtrip
7-Night Caribbean Cruise
$3,099
Windstar Cruises – Star Pride
90 Reviews
Departs Nov 30, 2024 from San Juan, Puerto Rico
Up to 3 deals including Avoya Exclusives
7-Night Caribbean Cruise
$1,998
Windstar Cruises – Star Pride
90 Reviews
Departs Dec 07, 2024 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 Dec 07, 2024 from Bridgetown, Barbados
Up to 3 deals including Avoya Exclusives
14-Night Caribbean Cruise
$3,598
Windstar Cruises – Star Pride
90 Reviews
Departs Dec 07, 2024 from San Juan, Puerto Rico
Up to 3 deals including Avoya Exclusives
Roundtrip
14-Night Caribbean Cruise
$4,799
Windstar Cruises – Wind Spirit
98 Reviews
Departs Dec 07, 2024 from Bridgetown, Barbados
Up to 3 deals including Avoya Exclusives
7-Night Caribbean Cruise
$1,998
Windstar Cruises – Star Pride
90 Reviews
Departs Dec 14, 2024 from Bridgetown, Barbados
Up to 3 deals including Avoya Exclusives
Roundtrip
7-Night Caribbean Cruise
$2,899
Windstar Cruises – Wind Spirit
98 Reviews
Departs Dec 14, 2024 from Bridgetown, Barbados
Up to 3 deals including Avoya Exclusives
Roundtrip
14-Night Caribbean Cruise
$4,999
Windstar Cruises – Wind Spirit
98 Reviews
Departs Dec 14, 2024 from Bridgetown, Barbados
Up to 3 deals including Avoya Exclusives
Roundtrip
7-Night Caribbean Cruise
$2,398
Windstar Cruises – Wind Surf
145 Reviews
Departs Dec 21, 2024 from Saint Maarten (Phillipsburg), Netherlands Antilles
Up to 3 deals including Avoya Exclusives
Roundtrip
7-Night Caribbean Cruise
$3,299
Windstar Cruises – Wind Spirit
98 Reviews
Departs Dec 21, 2024 from Bridgetown, Barbados
Up to 3 deals including Avoya Exclusives
Roundtrip
7-Night Caribbean Cruise
$4,099
Windstar Cruises – Wind Surf
145 Reviews
Departs Dec 28, 2024 from Saint Maarten (Phillipsburg), Netherlands Antilles
Up to 3 deals including Avoya Exclusives
Roundtrip
7-Night Caribbean Cruise
$2,398
Windstar Cruises – Wind Spirit
98 Reviews
Departs Jan 04, 2025 from Bridgetown, Barbados
Up to 3 deals including Avoya Exclusives
7-Night Caribbean Cruise
$2,676
Windstar Cruises – Star Pride
90 Reviews
Departs Jan 04, 2025 from Oranjestad, Aruba
Up to 3 deals including Avoya Exclusives
Roundtrip
7-Night Caribbean Cruise
$2,719
Windstar Cruises – Wind Surf
145 Reviews
Departs Jan 04, 2025 from Saint Maarten (Phillipsburg), Netherlands Antilles
Up to 3 deals including Avoya Exclusives
Roundtrip
14-Night Caribbean Cruise
$5,429
Windstar Cruises – Wind Spirit
98 Reviews
Departs Jan 04, 2025 from Bridgetown, Barbados
Up to 3 deals including Avoya Exclusives
Roundtrip
14-Night Caribbean Cruise
$6,799
Windstar Cruises – Wind Surf
145 Reviews
Departs Jan 04, 2025 from Saint Maarten (Phillipsburg), Netherlands Antilles
Up to 3 deals including Avoya Exclusives
Roundtrip
7-Night Caribbean Cruise
$3,699
Windstar Cruises – Wind Spirit
98 Reviews
Departs Jan 11, 2025 from Bridgetown, Barbados
Up to 3 deals including Avoya Exclusives
Roundtrip
7-Night Caribbean Cruise
$3,799
Windstar Cruises – Wind Surf
145 Reviews
Departs Jan 11, 2025 from Saint Maarten (Phillipsburg), Netherlands Antilles
Up to 3 deals including Avoya Exclusives
7-Night Caribbean Cruise
$4,999
Windstar Cruises – Star Pride
90 Reviews
Departs Jan 11, 2025 from Bridgetown, Barbados
Up to 3 deals including Avoya Exclusives
Roundtrip
14-Night Caribbean Cruise
$6,799
Windstar Cruises – Wind Surf
145 Reviews
Departs Jan 11, 2025 from Saint Maarten (Phillipsburg), Netherlands Antilles
Up to 3 deals including Avoya Exclusives
Roundtrip
14-Night Caribbean Cruise
$11,099
Windstar Cruises – Wind Spirit
98 Reviews
Departs Jan 11, 2025 from Bridgetown, Barbados
Up to 3 deals including Avoya Exclusives
Roundtrip
7-Night Caribbean Cruise
$3,399
Windstar Cruises – Wind Surf
145 Reviews
Departs Jan 18, 2025 from Saint Maarten (Phillipsburg), Netherlands Antilles
Up to 3 deals including Avoya Exclusives
Roundtrip
7-Night Caribbean Cruise
$3,799
Windstar Cruises – Wind Spirit
98 Reviews
Departs Jan 18, 2025 from Bridgetown, Barbados
Up to 3 deals including Avoya Exclusives
Roundtrip
14-Night Caribbean Cruise
$5,899
Windstar Cruises – Wind Surf
145 Reviews
Departs Jan 18, 2025 from Saint Maarten (Phillipsburg), Netherlands Antilles
Up to 3 deals including Avoya Exclusives
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