Windstar

Windstar Cruises to Southern Caribbean

Colorful buildings along the waterfront of Oranjestad, Aruba, a vibrant port of call for a Windstar cruise in the Southern Caribbean.

Upcoming Windstar Cruises to Southern Caribbean

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A vibrant orange and red sunset over the tranquil harbor in Sydney, Nova Scotia, with the setting sun reflecting on the water.
Up to $500 FREE Onboard Credit*+ 2 more offers
TCW EXCLUSIVE
Windstar

25-night Star Collector Cruise: Autumn In Newfoundland And New England

Aboard

Star Pride

From

Boston, Massachusetts

Published prices from

$16,565

per person*

taxes & fees included

A beautiful shot of the rocky coastline of Baie-Comeau, a port city in Quebec, Canada, with rugged cliffs covered in pine trees meeting the calm, reflective waters of the bay.
FREE All-Inclusive Upgrade*+ 1 more offer
Windstar

25-night Star Collector Cruise: Autumn In Newfoundland And New England

Aboard

Star Pride

From

Montreal, Quebec

Published prices from

$16,565

per person*

taxes & fees included

A charming white and red lighthouse, perched on a dramatic red cliff overlooking the ocean, with lush green grass and a few houses under a bright blue sky on Cap-aux-Meules, Quebec.
FREE All-Inclusive Upgrade*+ 1 more offer
Windstar

14-night Quebec And Newfoundland Adventure Cruise

Aboard

Star Pride

From

Montreal, Quebec

Published prices from

$5,250

per person*

taxes & fees included

Blue Mosque and historic Istanbul skyline with Bosphorus Strait.
FREE All-Inclusive Upgrade*+ 1 more offer
Windstar

70-night Star Collector: Grand Mediterranean And Latin America Adventure Cruise

Aboard

Star Legend

From

Istanbul, Turkey

An aerial panoramic view of a winding road overlooking Frigate Bay and the Caribbean Sea, with rolling green hills, a beach, and the town of Basseterre, St. Kitts.
FREE All-Inclusive Upgrade*+ 1 more offer
Windstar

11-night Gems Of The Leeward Islands Cruise

Aboard

Star Pride

From

San Juan, Puerto Rico

Published prices from

$4,257

per person*

taxes & fees included

Alcazaba fortress in Malaga.
Up to $500 FREE Onboard Credit*+ 2 more offers
TCW EXCLUSIVE
Windstar

24-night Star Collector: Classic Crossing To Spain & More Cruise

Aboard

Wind Star

From

Barcelona, Spain

An idyllic white-sand beach with turquoise water and palm trees on Jost Van Dyke, with a lush green hill in the background.
FREE All-Inclusive Upgrade*+ 1 more offer
Windstar

14-night Star Collector: Lovely Leewards Cruise

Aboard

Star Pride

From

San Juan, Puerto Rico

Published prices from

$4,593

per person*

taxes & fees included

A picturesque view of a small town nestled at the base of a lush, green mountain on Iles des Saintes, Guadeloupe, with boats moored in the deep blue water and fluffy clouds in the sky.
FREE All-Inclusive Upgrade*+ 1 more offer
Windstar

7-night Windward Islands Surf & Sunsets Cruise

Aboard

Star Pride

From

San Juan, Puerto Rico

Published prices from

$2,930

per person*

taxes & fees included

Belém Tower on Tagus River.
FREE All-Inclusive Upgrade*+ 1 more offer
Windstar

14-night Ocean Crossings Cruise

Aboard

Wind Star

From

Lisbon, Portugal

An aerial view of the Kralendijk waterfront in Bonaire, showcasing the contrast between the deep blue ocean and the shallow turquoise water near the shore, with sailboats anchored offshore.
FREE All-Inclusive Upgrade*+ 1 more offer
Windstar

25-night Star Collector: Southern Caribbean Thanksgiving Jubilee Cruise

Aboard

Wind Star

From

Lisbon, Portugal

A picturesque view of the historic Cape Spartel Lighthouse on a cliff overlooking the Atlantic Ocean near Tangier, Morocco.
FREE All-Inclusive Upgrade*
Windstar

13-night Ocean Crossings Cruise

Aboard

Star Legend

From

Malaga, Spain

Published prices from

$3,304

per person*

taxes & fees included

A close-up of a small, adorable squirrel monkey with a black cap and a light brown body, perched on a tree branch surrounded by lush, yellow-green leaves.
FREE All-Inclusive Upgrade*+ 1 more offer
Windstar

18-night Star Collector: Reefs & Rainforests: The Caribbean, Colombia, Panama & Costa Rica Via The Panama Canal Cruise

Aboard

Wind Star

From

Bridgetown, Barbados

A scenic view of a pristine beach on the San Blas Islands, Panama, with a line of tall palm trees casting shadows on the white sand and clear turquoise water.
FREE All-Inclusive Upgrade*+ 1 more offer
Windstar

11-night Colombian & Southern Caribbean Coastlines Cruise

Aboard

Wind Star

From

Bridgetown, Barbados

Published prices from

$5,730

per person*

taxes & fees included

A sunny view of the colorful waterfront of Willemstad, Curacao, with its iconic pastel-colored Dutch colonial buildings lining the Handelskade street and a ship docked in the port.
FREE All-Inclusive Upgrade*+ 1 more offer
Windstar

15-night Star Collector: Captivating Caribbean Cruise

Aboard

Star Legend

From

Bridgetown, Barbados

Published prices from

$5,358

per person*

taxes & fees included

Rocky beach and palm trees in Barbados.
FREE All-Inclusive Upgrade*+ 1 more offer
Windstar

7-night Jewels Of The Windward Islands Cruise

Aboard

Star Legend

From

Bridgetown, Barbados

Published prices from

$2,838

per person*

taxes & fees included

An aerial view of the Kralendijk waterfront in Bonaire, showcasing the contrast between the deep blue ocean and the shallow turquoise water near the shore, with sailboats anchored offshore.
FREE All-Inclusive Upgrade*+ 1 more offer
Windstar

16-night Star Collector: Windward Islands & Spanish New World Cruise

Aboard

Star Legend

From

Bridgetown, Barbados

Published prices from

$5,611

per person*

taxes & fees included

A beautiful view from Fort King George in Scarborough, Tobago, with historic cannons overlooking the Caribbean Sea and the town below, framed by lush tropical trees.
FREE All-Inclusive Upgrade*+ 1 more offer
Windstar

8-night Windward Ways & Tobago Cays Cruise

Aboard

Star Legend

From

Bridgetown, Barbados

Published prices from

$3,519

per person*

taxes & fees included

A cruise ship navigating through the Gatun Locks of the Panama Canal, an important navigational route and popular tourist destination.
FREE All-Inclusive Upgrade*+ 1 more offer
Windstar

8-night Panama Canal, Cartagena, San Blas Islands & More Cruise

Aboard

Star Legend

From

Oranjestad, Aruba, Caribbean

Published prices from

$3,365

per person*

taxes & fees included

A scenic view of a pristine beach on the San Blas Islands, Panama, with a line of tall palm trees casting shadows on the white sand and clear turquoise water.
FREE All-Inclusive Upgrade*+ 1 more offer
Windstar

16-night Star Collector: Latin America Explorer Cruise

Aboard

Star Legend

From

Oranjestad, Aruba, Caribbean

Published prices from

$5,427

per person*

taxes & fees included

A picturesque view of a small town nestled at the base of a lush, green mountain on Iles des Saintes, Guadeloupe, with boats moored in the deep blue water and fluffy clouds in the sky.
FREE All-Inclusive Upgrade*+ 1 more offer
Windstar

14-night Star Collector: Caribbean Explorations Cruise

Aboard

Wind Surf

From

Philipsburg, St. Maarten, The Netherlands

Published prices from

$5,419

per person*

taxes & fees included

Cupecoy Beach with white resort buildings, St. Maarten.
FREE All-Inclusive Upgrade*+ 1 more offer
Windstar

7-night Classic Caribbean Cruise

Aboard

Wind Surf

From

Philipsburg, St. Maarten, The Netherlands

Published prices from

$2,851

per person*

taxes & fees included

A dreamy long-exposure shot of the coastline in Manuel Antonio National Park near Quepos, Costa Rica, with a tranquil, misty ocean flowing between large, jagged rocks and a lush green headland in the distance at sunset.
FREE All-Inclusive Upgrade*
Windstar

13-night Latin America Explorer Cruise

Aboard

Star Legend

From

Puerto Caldera, Costa Rica

Published prices from

$5,627

per person*

taxes & fees included

An aerial view of Bocas del Toro, a vibrant town on the Caribbean coast of Panama, featuring colorful houses built over clear blue water and numerous sailboats docked nearby.
FREE All-Inclusive Upgrade*
Windstar

6-night Panama Canal, Cartagena, San Blas Islands & More Cruise

Aboard

Star Legend

From

Fuerte Amador, Panama

Published prices from

$3,665

per person*

taxes & fees included

Panama City skyline from water.
FREE All-Inclusive Upgrade*
Windstar

14-night Star Collector: Windward Islands & Spanish New World Cruise

Aboard

Star Legend

From

Fuerte Amador, Panama

Published prices from

$6,785

per person*

taxes & fees included

A sunny view of the colorful waterfront of Willemstad, Curacao, with its iconic pastel-colored Dutch colonial buildings lining the Handelskade street and a ship docked in the port.
FREE All-Inclusive Upgrade*
Windstar

8-night Windward Ways & Tobago Cays Cruise

Aboard

Star Legend

From

Oranjestad, Aruba, Caribbean

Published prices from

$4,019

per person*

taxes & fees included

Historic Halifax waterfront buildings.
Windstar

25-night Star Collector: Autumn In Newfoundland And New England Cruise

Aboard

Star Pride

From

Boston, Massachusetts

Published prices from

$10,065

per person*

taxes & fees included

A cruise ship navigating through the Gatun Locks of the Panama Canal, an important navigational route and popular tourist destination.
Windstar

7-night Panama Canal, Cartagena, San Blas Islands & More Cruise

Aboard

Star Pride

From

Balboa, Panama

Published prices from

$3,365

per person*

taxes & fees included

*Rates and offers are per person, in US Dollars, based on double occupancy, capacity controlled, subject to availability and confirmation, and may change without notice. Government taxes and fees are included. Rates and offers are available for select dates and categories only. Additional restrictions may apply. Call 1-800-377-9383 for full terms and conditions.

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Destinations

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Ports

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Karukinka, Tierra del Fuego

Ilheus, Brazil

Cruise Ships

Norwegian Sky

AmaSofia

Norwegian Jewel

S.S. São Gabriel

Wonder of the Seas