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Windstar Cruises to the Caribbean

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Windstar Cruises to the Caribbean

We found you 53 cruises

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Star Pride
Star Pride

11 Night
Gems Of The Leeward Islands 11d Sju-sju Details

109 Reviews
Leaving:San Juan
Cruise Line:Windstar Cruises
Dec 27, 2022
No prices currently available for this sailing.
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Star Pride
Star Pride

7 Night
San Juan & The Virgin Islands 7d Sju-sju Details

Leaving:San Juan
Cruise Line:Windstar Cruises
Nov 19, 2022
No prices currently available for this sailing.
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Wind Star
Wind Star

7 Night
Costa Rica & Panama Canal 7d Onx-ptc Details

Leaving:Colon
Cruise Line:Windstar Cruises
Jan 7, 2023
No prices currently available for this sailing.
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Wind Surf
Wind Surf

7 Night
Jewels Of Windward Islands 7d Bgi-bgi Details

Leaving:Barbados
Cruise Line:Windstar Cruises
Mar 4, 2023
No prices currently available for this sailing.
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Sponsored

Up to $400 more while sailing the Med

  • Up to $400 on board credit per cabin on select Mediterranean voyages
  • Cruise Critic Editor’s Choice for Best New Ship in the US for 2021
  • Caribbean and Mediterranean itineraries
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Virgin Voyages

7 Night
Classic Caribbean 7d Ph1-ph1 Details

Leaving:St. Maarten
Cruise Line:Windstar Cruises
Dec 10, 2022
No prices currently available for this sailing.
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7 Night
Spanish Treasures Via The Panama Canal 7d Orj-pty Details

Leaving:Aruba
Cruise Line:Windstar Cruises
Feb 25, 2023
No prices currently available for this sailing.
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7 Night
Costa Rica & Panama Canal 7d Onx-ptc Details

Leaving:Colon
Cruise Line:Windstar Cruises
Feb 18, 2023
No prices currently available for this sailing.
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7 Night
Spanish Treasures Via The Panama Canal 7d Orj-pty Details

Leaving:Aruba
Cruise Line:Windstar Cruises
Jan 28, 2023
No prices currently available for this sailing.
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Cruise Critic Favorite

7 Night
Yachtsmans Caribbean 7d Ph1-ph1 Details

Leaving:St. Maarten
Cruise Line:Windstar Cruises
Jan 21, 2023
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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7 Night
Windward Ways & Tobago Cays 7d Orj-bgi Details

Leaving:Aruba
Cruise Line:Windstar Cruises
Feb 11, 2023
No prices currently available for this sailing.
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7 Night
Jewels Of Windward Islands 7d Bgi-bgi Details

Leaving:Barbados
Cruise Line:Windstar Cruises
Feb 4, 2023
No prices currently available for this sailing.
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Cruise Critic Favorite

7 Night
Yachtsmans Caribbean 7d Ph1-ph1 Details

Leaving:St. Maarten
Cruise Line:Windstar Cruises
Jan 7, 2023
No prices currently available for this sailing.
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Cruise Critic Favorite

7 Night
Yachtsmans Caribbean 7d Ph1-ph1 Details

Leaving:St. Maarten
Cruise Line:Windstar Cruises
Mar 18, 2023
No prices currently available for this sailing.
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Cruise Critic Favorite

7 Night
Yachtsmans Caribbean 7d Ph1-ph1 Details

Leaving:St. Maarten
Cruise Line:Windstar Cruises
Feb 18, 2023
No prices currently available for this sailing.
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