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Windstar Cruises to the Caribbean

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Windstar Cruises to the Caribbean

We found you 91 cruises

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Star Legend
Star  Breeze pool lighting

7 Night
Spanish Treasures Via The Panama Canal 7d Orj-ptyDetails

121 Reviews
Leaving:Aruba
Cruise Line:Windstar Cruises
Mar 11, 2023
No prices currently available for this sailing.
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Wind Surf
Wind Surf

7 Night
Beach Fun & Sun: A Remote Caribbean Getaway 7d Ph1...Details

Leaving:St. Maarten
Cruise Line:Windstar Cruises
Feb 10, 2024
No prices currently available for this sailing.
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Star Legend
Star  Breeze pool lighting

7 Night
Windward Ways & Tobago Cays 7d Orj-bgiDetails

Leaving:Aruba
Cruise Line:Windstar Cruises
Feb 11, 2023
No prices currently available for this sailing.
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Star Pride
Windstar's stretched Star Pride (Photo/Melinda Crow)

7 Night
Windward Islands Surf & Sunsets 7d Sju-sjuDetails

Leaving:San Juan
Cruise Line:Windstar Cruises
Nov 26, 2022
No prices currently available for this sailing.
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7 Night
San Juan & The Virgin Islands 7d Sju-sjuDetails

Leaving:San Juan
Cruise Line:Windstar Cruises
Feb 25, 2023
No prices currently available for this sailing.
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7 Night
Windward Islands Surf & Sunsets 7d Sju-sjuDetails

Leaving:San Juan
Cruise Line:Windstar Cruises
Mar 4, 2023
No prices currently available for this sailing.
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Cruise Critic Favorite

7 Night
Jewels Of The Windward Islands 7d Bgi-bgiDetails

Leaving:Barbados
Cruise Line:Windstar Cruises
Mar 28, 2024
No prices currently available for this sailing.
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Cruise Critic Favorite

7 Night
Yachtsmans Caribbean 7d Ph1-ph1Details

Leaving:St. Maarten
Cruise Line:Windstar Cruises
Feb 18, 2023
No prices currently available for this sailing.
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7 Night
Costa Rica & Panama Canal 7d Ptc-onxDetails

Leaving:Puntarenas
Cruise Line:Windstar Cruises
Dec 10, 2022
No prices currently available for this sailing.
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7 Night
Lush & Lovely Islands Of The Lesser Antilles 7d Ph...Details

Leaving:St. Maarten
Cruise Line:Windstar Cruises
Feb 25, 2023
No prices currently available for this sailing.
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11 Night
Caribbean Pleasures 11d Ph1-ph1Details

Leaving:St. Maarten
Cruise Line:Windstar Cruises
Dec 27, 2022
No prices currently available for this sailing.
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7 Night
Lush & Lovely Islands Of The Lesser Antilles 7d Bg...Details

Leaving:Barbados
Cruise Line:Windstar Cruises
Mar 11, 2023
No prices currently available for this sailing.
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7 Night
Beach Fun & Sun: A Remote Caribbean Getaway 7d Ph1...Details

Leaving:St. Maarten
Cruise Line:Windstar Cruises
Dec 16, 2023
No prices currently available for this sailing.
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7 Night
Costa Rica & Panama Canal 7d Ptc-onxDetails

Leaving:Puntarenas
Cruise Line:Windstar Cruises
Mar 11, 2023
No prices currently available for this sailing.
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7 Night
San Juan & The Virgin Islands 7d Sju-sjuDetails

Leaving:San Juan
Cruise Line:Windstar Cruises
Dec 20, 2022
No prices currently available for this sailing.
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