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Windstar Cruises to Caribbean

Showing 26-50 of 139 results
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
$5,599
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
14-Night Caribbean Cruise
$5,699
Windstar Cruises – Wind Spirit
98 Reviews
Departs Jan 11, 2025 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 18, 2025 from Saint Maarten (Phillipsburg), Netherlands Antilles
Up to 3 deals including Avoya Exclusives
Roundtrip
7-Night Caribbean Cruise
$3,099
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
$5,429
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
$3,199
Windstar Cruises – Wind Spirit
98 Reviews
Departs Jan 25, 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 Jan 25, 2025 from Saint Maarten (Phillipsburg), Netherlands Antilles
Up to 2 deals including an Avoya Exclusive
Roundtrip
14-Night Caribbean Cruise
$6,379
Windstar Cruises – Wind Spirit
98 Reviews
Departs Jan 25, 2025 from Bridgetown, Barbados
Up to 2 deals including an Avoya Exclusive
Roundtrip
7-Night Caribbean Cruise
$3,499
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
$3,649
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
$5,539
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
14-Night Caribbean Cruise
$6,649
Windstar Cruises – Wind Spirit
98 Reviews
Departs Feb 01, 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 Feb 08, 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 Feb 08, 2025 from Bridgetown, Barbados
Up to 2 deals including an Avoya Exclusive
Roundtrip
14-Night Caribbean Cruise
$5,489
Windstar Cruises – Wind Surf
145 Reviews
Departs Feb 08, 2025 from Saint Maarten (Phillipsburg), Netherlands Antilles
Up to 2 deals including an Avoya Exclusive
Roundtrip
14-Night Caribbean Cruise
$6,499
Windstar Cruises – Wind Spirit
98 Reviews
Departs Feb 08, 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 Feb 15, 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 Feb 15, 2025 from Bridgetown, Barbados
Up to 2 deals including an Avoya Exclusive
Roundtrip
14-Night Caribbean Cruise
$5,449
Windstar Cruises – Wind Surf
145 Reviews
Departs Feb 15, 2025 from Saint Maarten (Phillipsburg), Netherlands Antilles
Up to 2 deals including an Avoya Exclusive
Roundtrip
7-Night Caribbean Cruise
$3,399
Windstar Cruises – Wind Surf
145 Reviews
Departs Feb 22, 2025 from Saint Maarten (Phillipsburg), Netherlands Antilles
Up to 2 deals including an Avoya Exclusive
7-Night Caribbean Cruise
$3,549
Windstar Cruises – Star Pride
90 Reviews
Departs Feb 22, 2025 from Bridgetown, Barbados
Up to 2 deals including an Avoya Exclusive
Roundtrip
14-Night Caribbean Cruise
$5,399
Windstar Cruises – Wind Surf
145 Reviews
Departs Feb 22, 2025 from Saint Maarten (Phillipsburg), Netherlands Antilles
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
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