Windstar Cruises to the Caribbean

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Windstar Cruises to the Caribbean

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Windstar's stretched Star Pride (Photo/Melinda Crow)
Star Pride
Star Pride Cabins
Star Pride
Cuadro 44 on Windstar's Star Pride (Photo/Melinda Crow)
Star Pride
Pool on Windstar's Star Pride (Photo/Melinda Crow)
Star Pride
Star Pride
Star Pride

7 Nights

Winter Antilles Escape 7c Sju-bgi

Port: San Juan • St. Thomas • St. Barts • Little Bay • Dominica • St. Lucia • Grenada • Barbados

128 reviews
Dec 7, 2024
Windstar Cruises
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7 Nights

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

Port: St. Maarten • Antigua • Road Bay • Sopers Hole • Jost Van Dyke • Virgin Gorda • St. Barts +1 more

259 reviews
Feb 1, 2025
Windstar Cruises
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7 Nights

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

Port: St. Maarten • Antigua • Road Bay • Sopers Hole • Jost Van Dyke • Virgin Gorda • St. Barts +1 more

259 reviews
Feb 15, 2025
Windstar Cruises
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Windstar's stretched Star Pride (Photo/Melinda Crow)
Star Pride
Star Pride Cabins
Star Pride
Cuadro 44 on Windstar's Star Pride (Photo/Melinda Crow)
Star Pride
Pool on Windstar's Star Pride (Photo/Melinda Crow)
Star Pride
Star Pride
Star Pride

7 Nights

Windward Ways & Tobago Cays 7d Orj-bgi

Port: Aruba • Willemstad • Bonaire • Soufriere • Mayreau • Barbados

128 reviews
Mar 15, 2025
Windstar Cruises
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Cruise Critic Favorite

10 Nights

Hidden Treasures Of The Lesser Antilles 10d Bgi-bg...

Port: Barbados • St. Kitts • St. Barts • Sopers Hole • Jost Van Dyke • Virgin Gorda • Iles des Saintes +2 more

105 reviews
Nov 27, 2024
Windstar Cruises
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Cruise Critic Favorite

7 Nights

Naturally Costa Rica 7d Ptc-ptc

Port: Puntarenas • Playa Flamingo • Corinto • San Juan del Sur • Playas del Coco • Herradura +2 more

116 reviews
Feb 15, 2025
Windstar Cruises
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7 Nights

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

Port: St. Maarten • Antigua • Road Bay • Sopers Hole • Jost Van Dyke • Virgin Gorda • St. Barts +1 more

259 reviews
Mar 28, 2026
Windstar Cruises
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7 Nights

Windward Ways & Tobago Cays 7d Bgi-orj

Port: Barbados • Mayreau • Soufriere • Bonaire • Willemstad • Aruba

128 reviews
Jan 11, 2025
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7 Nights

Windward Islands Surf & Sunsets 7d Sju-sju

Port: San Juan • Grenada • Bequia • St. Lucia • Iles des Saintes • St. Maarten • San Juan

128 reviews
Nov 23, 2024
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7 Nights

Jewels Of The Windward Islands 7d Bgi-bgi

Port: Barbados • St. Lucia • Casablanca • Aabenraa • St. Vincent • Mayreau • Grenada • Bequia +1 more

105 reviews
Jan 4, 2025
Windstar Cruises
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7 Nights

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

Port: St. Maarten • Antigua • Road Bay • Sopers Hole • Jost Van Dyke • Virgin Gorda • St. Barts +1 more

259 reviews
Jan 25, 2025
Windstar Cruises
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7 Nights

San Juan & The Virgin Islands 7d Sju-sju

Port: San Juan • St. Thomas • St. Barts • Little Bay • St. Maarten • Jost Van Dyke • Virgin Gorda +1 more

128 reviews
Nov 30, 2024
Windstar Cruises
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7 Nights

Classic Caribbean 7d Ph1-ph1

Port: St. Maarten • Charlestown • Dominica • St. Lucia • Iles des Saintes • St. Kitts +2 more

259 reviews
Feb 8, 2025
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7 Nights

Costa Rica & Panama Canal 7d Ptc-onx

Port: Puntarenas • Quepos • Puerto Jimenez • Isla Parida • Balboa • Panama Canal • Colon

128 reviews
Feb 16, 2026
Windstar Cruises
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7 Nights

Windward Ways & Tobago Cays 7d Bgi-orj

Port: Barbados • Mayreau • Soufriere • Bonaire • Willemstad • Aruba

128 reviews
Feb 22, 2025
Windstar Cruises
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