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Windstar Cruises to Caribbean

Showing 1-25 of 116 results
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
$4,199
Windstar Cruises – Wind Spirit
98 Reviews
Departs Dec 28, 2024 from Bridgetown, Barbados
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
$3,199
Windstar Cruises – Star Pride
91 Reviews
Departs Jan 04, 2025 from Oranjestad, Aruba
Up to 2 deals including an Avoya Exclusive
Roundtrip
7-Night Caribbean Cruise
$3,499
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
$5,599
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
$2,558
Windstar Cruises – Wind Surf
145 Reviews
Departs Jan 11, 2025 from Saint Maarten (Phillipsburg), Netherlands Antilles
Up to 2 deals including an Avoya Exclusive
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
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
7-Night Caribbean Cruise
$2,239
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
14-Night Caribbean Cruise
$5,899
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
$6,099
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
$10,899
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
$2,379
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
$3,599
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
$2,878
Windstar Cruises – Wind Surf
145 Reviews
Departs Feb 01, 2025 from Saint Maarten (Phillipsburg), Netherlands Antilles
Up to 3 deals including Avoya Exclusives
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
$3,199
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
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
7-Night Caribbean Cruise
$2,413
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
$5,599
Windstar Cruises – Wind Surf
145 Reviews
Departs Feb 15, 2025 from Saint Maarten (Phillipsburg), Netherlands Antilles
Up to 2 deals including an Avoya Exclusive
7-Night Caribbean Cruise
$2,379
Windstar Cruises – Star Pride
91 Reviews
Departs Feb 22, 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 22, 2025 from Saint Maarten (Phillipsburg), Netherlands Antilles
Up to 2 deals including an Avoya Exclusive
14-Night Caribbean Cruise
$4,899
Windstar Cruises – Star Pride
91 Reviews
Departs Feb 22, 2025 from Bridgetown, Barbados
Up to 2 deals including an Avoya Exclusive
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