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Windstar Cruises to Caribbean

Showing 1-25 of 70 results
Roundtrip
7-Night Caribbean Cruise
$1,499
Windstar Cruises – Star Pride
86 Reviews
Departs Nov 04, 2023 from Philipsburg, Sint Maarten
Up to 1 deal
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7-Night Caribbean Cruise
$1,499
Windstar Cruises – Star Pride
86 Reviews
Departs Nov 11, 2023 from Philipsburg, Sint Maarten
Up to 1 deal
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Roundtrip
7-Night Caribbean Cruise
$1,799
Windstar Cruises – Star Pride
86 Reviews
Departs Nov 18, 2023 from Bridgetown, Barbados
Up to 1 deal
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7-Night Caribbean Cruise
$2,199
Windstar Cruises – Star Pride
86 Reviews
Departs Nov 25, 2023 from Bridgetown, Barbados
Up to 1 deal
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Roundtrip
7-Night Caribbean Cruise
$1,999
Windstar Cruises – Wind Surf
137 Reviews
Departs Dec 09, 2023 from Philipsburg, Sint Maarten
Up to 1 deal
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6-Night Caribbean Cruise
$1,099
Windstar Cruises – Star Pride
86 Reviews
Departs Dec 16, 2023 from Oranjestad, Aruba
Up to 1 deal
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Roundtrip
7-Night Caribbean Cruise
$1,999
Windstar Cruises – Wind Surf
137 Reviews
Departs Dec 16, 2023 from Philipsburg, Sint Maarten
Up to 1 deal
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11-Night Caribbean Cruise
$2,399
Windstar Cruises – Wind Star
86 Reviews
Departs Dec 19, 2023 from Bridgetown, Barbados
Up to 1 deal
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8-Night Caribbean Cruise
$2,199
Windstar Cruises – Star Pride
86 Reviews
Departs Dec 22, 2023 from Bridgetown, Barbados
Up to 1 deal
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Roundtrip
7-Night Caribbean Cruise
$2,999
Windstar Cruises – Wind Surf
137 Reviews
Departs Dec 23, 2023 from Philipsburg, Sint Maarten
Up to 1 deal
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Roundtrip
7-Night Caribbean Cruise
$2,899
Windstar Cruises – Wind Surf
137 Reviews
Departs Dec 30, 2023 from Philipsburg, Sint Maarten
Up to 1 deal
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Roundtrip
7-Night Caribbean Cruise
$2,199
Windstar Cruises – Wind Surf
137 Reviews
Departs Jan 06, 2024 from Philipsburg, Sint Maarten
Up to 1 deal
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7-Night Caribbean Cruise
$2,499
Windstar Cruises – Star Pride
86 Reviews
Departs Jan 13, 2024 from Oranjestad, Aruba
Up to 1 deal
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Roundtrip
7-Night Caribbean Cruise
$2,599
Windstar Cruises – Wind Surf
137 Reviews
Departs Jan 13, 2024 from Philipsburg, Sint Maarten
Up to 1 deal
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7-Night Caribbean Cruise
$2,399
Windstar Cruises – Star Pride
86 Reviews
Departs Jan 20, 2024 from Bridgetown, Barbados
Up to 1 deal
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Roundtrip
7-Night Caribbean Cruise
$2,399
Windstar Cruises – Wind Surf
137 Reviews
Departs Jan 20, 2024 from Philipsburg, Sint Maarten
Up to 1 deal
Save
Roundtrip
7-Night Caribbean Cruise
$2,599
Windstar Cruises – Wind Surf
137 Reviews
Departs Jan 27, 2024 from Philipsburg, Sint Maarten
Up to 1 deal
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Roundtrip
7-Night Caribbean Cruise
$2,299
Windstar Cruises – Wind Surf
137 Reviews
Departs Feb 03, 2024 from Philipsburg, Sint Maarten
Up to 1 deal
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Roundtrip
7-Night Caribbean Cruise
$2,599
Windstar Cruises – Wind Surf
137 Reviews
Departs Feb 10, 2024 from Philipsburg, Sint Maarten
Up to 1 deal
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7-Night Caribbean Cruise
$2,599
Windstar Cruises – Star Pride
86 Reviews
Departs Feb 10, 2024 from Oranjestad, Aruba
Up to 1 deal
Save
Roundtrip
7-Night Caribbean Cruise
$2,199
Windstar Cruises – Wind Surf
137 Reviews
Departs Feb 17, 2024 from Philipsburg, Sint Maarten
Up to 1 deal
Save
Roundtrip
7-Night Caribbean Cruise
$2,599
Windstar Cruises – Wind Surf
137 Reviews
Departs Feb 24, 2024 from Philipsburg, Sint Maarten
Up to 1 deal
Save
Roundtrip
7-Night Caribbean Cruise
$2,199
Windstar Cruises – Wind Surf
137 Reviews
Departs Mar 02, 2024 from Philipsburg, Sint Maarten
Up to 1 deal
Save
7-Night Caribbean Cruise
$2,199
Windstar Cruises – Star Pride
86 Reviews
Departs Mar 09, 2024 from Oranjestad, Aruba
Up to 1 deal
Save
Roundtrip
7-Night Caribbean Cruise
$2,399
Windstar Cruises – Wind Surf
137 Reviews
Departs Mar 09, 2024 from Philipsburg, Sint Maarten
Up to 1 deal
Save
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