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Windstar Cruises to Caribbean

Showing 1-25 of 56 results
Roundtrip
7-Night Caribbean Cruise
$2,899
Windstar Cruises – Star Pride
90 Reviews
Departs Nov 23, 2024 from San Juan, Puerto Rico
Up to 2 deals including an Avoya Exclusive
Roundtrip
14-Night Caribbean Cruise
$6,299
Windstar Cruises – Star Pride
90 Reviews
Departs Nov 23, 2024 from San Juan, Puerto Rico
Up to 2 deals including an Avoya Exclusive
Roundtrip
10-Night Caribbean Cruise
$3,999
Windstar Cruises – Wind Spirit
98 Reviews
Departs Nov 27, 2024 from Bridgetown, Barbados
Up to 2 deals including an Avoya Exclusive
Roundtrip
7-Night Caribbean Cruise
$3,149
Windstar Cruises – Star Pride
90 Reviews
Departs Nov 30, 2024 from San Juan, Puerto Rico
Up to 2 deals including an Avoya Exclusive
7-Night Caribbean Cruise
$1,998
Windstar Cruises – Star Pride
90 Reviews
Departs Dec 07, 2024 from San Juan, Puerto Rico
Up to 2 deals including an Avoya Exclusive
Roundtrip
7-Night Caribbean Cruise
$2,599
Windstar Cruises – Wind Spirit
98 Reviews
Departs Dec 07, 2024 from Bridgetown, Barbados
Up to 2 deals including an Avoya Exclusive
14-Night Caribbean Cruise
$3,598
Windstar Cruises – Star Pride
90 Reviews
Departs Dec 07, 2024 from San Juan, Puerto Rico
Up to 2 deals including an Avoya Exclusive
Roundtrip
14-Night Caribbean Cruise
$4,799
Windstar Cruises – Wind Spirit
98 Reviews
Departs Dec 07, 2024 from Bridgetown, Barbados
Up to 2 deals including an Avoya Exclusive
7-Night Caribbean Cruise
$1,998
Windstar Cruises – Star Pride
90 Reviews
Departs Dec 14, 2024 from Bridgetown, Barbados
Up to 2 deals including an Avoya Exclusive
Roundtrip
7-Night Caribbean Cruise
$2,293
Windstar Cruises – Wind Spirit
98 Reviews
Departs Dec 14, 2024 from Bridgetown, Barbados
Up to 2 deals including an Avoya Exclusive
Roundtrip
14-Night Caribbean Cruise
$4,999
Windstar Cruises – Wind Spirit
98 Reviews
Departs Dec 14, 2024 from Bridgetown, Barbados
Up to 2 deals including an Avoya Exclusive
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 2 deals including an Avoya Exclusive
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 2 deals including an Avoya Exclusive
Roundtrip
7-Night Caribbean Cruise
$3,499
Windstar Cruises – Wind Surf
145 Reviews
Departs Jan 11, 2025 from Saint Maarten (Phillipsburg), Netherlands Antilles
Up to 2 deals including an Avoya Exclusive
7-Night Caribbean Cruise
$3,599
Windstar Cruises – Star Pride
90 Reviews
Departs Jan 11, 2025 from Bridgetown, Barbados
Up to 2 deals including an Avoya Exclusive
Roundtrip
14-Night Caribbean Cruise
$5,699
Windstar Cruises – Wind Spirit
98 Reviews
Departs Jan 18, 2025 from Bridgetown, Barbados
Up to 2 deals including an Avoya Exclusive
Roundtrip
7-Night Caribbean Cruise
$4,049
Windstar Cruises – Wind Spirit
98 Reviews
Departs Feb 01, 2025 from Bridgetown, Barbados
Up to 2 deals including an Avoya Exclusive
Roundtrip
14-Night Caribbean Cruise
$5,699
Windstar Cruises – Wind Surf
145 Reviews
Departs Feb 01, 2025 from Saint Maarten (Phillipsburg), Netherlands Antilles
Up to 2 deals including an Avoya Exclusive
Roundtrip
7-Night Caribbean Cruise
$3,299
Windstar Cruises – Wind Spirit
98 Reviews
Departs Feb 15, 2025 from Bridgetown, Barbados
Up to 2 deals including an Avoya Exclusive
7-Night Caribbean Cruise
$3,649
Windstar Cruises – Star Pride
90 Reviews
Departs Feb 22, 2025 from Bridgetown, Barbados
Up to 2 deals including an Avoya Exclusive
Roundtrip
7-Night Caribbean Cruise
$3,399
Windstar Cruises – Wind Surf
145 Reviews
Departs Mar 01, 2025 from Saint Maarten (Phillipsburg), Netherlands Antilles
Up to 2 deals including an Avoya Exclusive
Roundtrip
14-Night Caribbean Cruise
$5,399
Windstar Cruises – Wind Surf
145 Reviews
Departs Mar 08, 2025 from Saint Maarten (Phillipsburg), Netherlands Antilles
Up to 2 deals including an Avoya Exclusive
7-Night Caribbean Cruise
$3,199
Windstar Cruises – Star Pride
90 Reviews
Departs Mar 15, 2025 from Oranjestad, Aruba
Up to 2 deals including an Avoya Exclusive
Roundtrip
7-Night Caribbean Cruise
$3,199
Windstar Cruises – Wind Surf
145 Reviews
Departs Mar 15, 2025 from Saint Maarten (Phillipsburg), Netherlands Antilles
Up to 2 deals including an Avoya Exclusive
Roundtrip
14-Night Caribbean Cruise
$4,599
Windstar Cruises – Star Pride
90 Reviews
Departs Nov 02, 2025 from San Juan, Puerto Rico
Up to 2 deals including an Avoya Exclusive
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