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Windstar Cruises to Caribbean

Showing 1-25 of 129 results
7-Night Caribbean Cruise
$1,998
Windstar Cruises – Star Pride
91 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
$3,868
Windstar Cruises – Star Pride
91 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
91 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
$3,299
Windstar Cruises – Wind Surf
145 Reviews
Departs Dec 21, 2024 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 Dec 21, 2024 from Bridgetown, Barbados
Up to 2 deals including an Avoya Exclusive
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 2 deals including an Avoya Exclusive
Roundtrip
7-Night Caribbean Cruise
$2,239
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
$2,398
Windstar Cruises – Wind Spirit
98 Reviews
Departs Jan 04, 2025 from Bridgetown, Barbados
Up to 2 deals including an Avoya Exclusive
7-Night Caribbean Cruise
$2,519
Windstar Cruises – Star Pride
91 Reviews
Departs Jan 04, 2025 from Oranjestad, Aruba
Up to 2 deals including an Avoya Exclusive
Roundtrip
14-Night Caribbean Cruise
$4,079
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
$5,429
Windstar Cruises – Wind Spirit
98 Reviews
Departs Jan 04, 2025 from Bridgetown, Barbados
Up to 2 deals including an Avoya Exclusive
Roundtrip
7-Night Caribbean Cruise
$2,558
Windstar Cruises – Wind Surf
145 Reviews
Departs Jan 11, 2025 from Saint Maarten (Phillipsburg), Netherlands Antilles
Up to 2 deals including an Avoya Exclusive
Roundtrip
7-Night Caribbean Cruise
$3,699
Windstar Cruises – Wind Spirit
98 Reviews
Departs Jan 11, 2025 from Bridgetown, Barbados
Up to 2 deals including an Avoya Exclusive
Roundtrip
14-Night Caribbean Cruise
$5,099
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
$5,399
Windstar Cruises – Star Pride
91 Reviews
Departs Jan 11, 2025 from Bridgetown, Barbados
Up to 2 deals including an Avoya Exclusive
Roundtrip
7-Night Caribbean Cruise
$3,199
Windstar Cruises – Wind Surf
145 Reviews
Departs Jan 18, 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 Spirit
98 Reviews
Departs Jan 18, 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
14-Night Caribbean Cruise
$5,699
Windstar Cruises – Wind Surf
145 Reviews
Departs Jan 18, 2025 from Saint Maarten (Phillipsburg), Netherlands Antilles
Up to 2 deals including an Avoya Exclusive
Roundtrip
7-Night Caribbean Cruise
$2,718
Windstar Cruises – Wind Surf
145 Reviews
Departs Jan 25, 2025 from Saint Maarten (Phillipsburg), Netherlands Antilles
Up to 2 deals including an Avoya Exclusive
Roundtrip
7-Night Caribbean Cruise
$3,199
Windstar Cruises – Wind Spirit
98 Reviews
Departs Jan 25, 2025 from Bridgetown, Barbados
Up to 2 deals including an Avoya Exclusive
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