Windstar

Windstar Cruises to Caribbean

White sand beach with boulders and palm trees in Virgin Gorda, a beautiful Caribbean destination for a Windstar cruise.

Upcoming Windstar Cruises to Caribbean

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A picturesque view of a red and white lighthouse on a rocky cliff overlooking the vast Atlantic Ocean in St. Anthony, Newfoundland and Labrador.
Windstar

25-night Star Collector Cruise: Autumn In Newfoundland And New England From Boston, Massachusetts

Aboard

Star Pride

From

Boston, Massachusetts

Published prices from

$11,498

per person*

taxes & fees included

A low-angle shot of a massive, imposing cliff face rising dramatically from the dark water, with patches of moss and greenery clinging to its textured, gray rock surface.
Windstar

25-night Star Collector Cruise: Autumn In Newfoundland And New England From Montreal, Quebec

Aboard

Star Pride

From

Montreal, Quebec

A stunning autumn landscape in Havre-Saint-Pierre, Quebec, with a lake reflecting a forest of trees in various shades of green, yellow, and orange, with a wooden pier in the foreground.
Windstar

14-night Quebec And Newfoundland Adventure Cruise From Montreal, Quebec

Aboard

Star Pride

From

Montreal, Quebec

Published prices from

$8,680

per person*

taxes & fees included

A breathtaking view of the unique, rocky coastline of St. George's, Bermuda, with a tall rock formation rising from the shallow, clear turquoise waters.
Windstar

19-night Star Collector: Fall Leaves & Caribbean Breezes Cruise From Montreal, Quebec

Aboard

Star Pride

From

Montreal, Quebec

Published prices from

$6,979

per person*

taxes & fees included

The iconic Library of Celsus in the ancient city of Ephesus, Turkey, with its magnificent, two-story facade and marble columns standing against a backdrop of cypress trees and green hills.
Windstar

70-night Star Collector: Grand Mediterranean And Latin America Adventure Cruise From Istanbul, Turkey

Aboard

Star Legend

From

Istanbul, Turkey

A turquoise and white ferry boat cruises through the harbor in Hamilton, Bermuda, with a backdrop of pastel-colored buildings and houses along the waterfront.
Windstar

8-night Bermuda Bliss Cruise From Boston, Massachusetts

Aboard

Star Pride

From

Boston, Massachusetts

Published prices from

$3,427

per person*

taxes & fees included

An aerial view of the colorful waterfront of St. George's, Grenada, with the town's buildings nestled on a hillside and a long, rocky breakwater extending into the calm, turquoise water.
Windstar

11-night Gems Of The Leeward Islands Cruise From San Juan, Puerto Rico

Aboard

Star Pride

From

San Juan, Puerto Rico

Published prices from

$4,568

per person*

taxes & fees included

Belém Tower on Tagus River.
Windstar

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

Aboard

Wind Star

From

Barcelona, Spain

A scenic view of the white sand beach and lush palm trees of Mystery Island, Aneityum, with calm, turquoise water under a clear blue sky.
Windstar

23-night Star Collector Cruise: Spanish Mystery & Atlantic Crossing From Barcelona, Spain

Aboard

Star Legend

From

Barcelona, Spain

Published prices from

$6,535

per person*

taxes & fees included

Historic El Morro fortress overlooking the ocean in San Juan, Puerto Rico.
Windstar

7-night Windward Islands Surf & Sunsets Cruise From San Juan, Puerto Rico

Aboard

Star Pride

From

San Juan, Puerto Rico

Published prices from

$2,516

per person*

taxes & fees included

An idyllic white-sand beach with turquoise water and palm trees on Jost Van Dyke, with a lush green hill in the background.
Windstar

14-night Star Collector: Lovely Leewards Cruise From San Juan, Puerto Rico

Aboard

Star Pride

From

San Juan, Puerto Rico

Published prices from

$4,070

per person*

taxes & fees included

Rocky beach and palm trees in Barbados.
Windstar

14-night Ocean Crossings Cruise From Lisbon, Portugal

Aboard

Wind Star

From

Lisbon, Portugal

Published prices from

$5,206

per person*

taxes & fees included

An aerial view of the colorful waterfront of St. George's, Grenada, with the town's buildings nestled on a hillside and a long, rocky breakwater extending into the calm, turquoise water.
Windstar

25-night Star Collector: Southern Caribbean Thanksgiving Jubilee Cruise From Lisbon, Portugal

Aboard

Wind Star

From

Lisbon, Portugal

Rocky beach and palm trees in Barbados.
Windstar

22-night Star Collector Cruise: Caribbean Beats & Transatlantic Treats From Malaga, Spain

Aboard

Star Legend

From

Malaga, Spain

Published prices from

$5,491

per person*

taxes & fees included

A picturesque view of the historic Cape Spartel Lighthouse on a cliff overlooking the Atlantic Ocean near Tangier, Morocco.
Windstar

13-night Ocean Crossings Cruise From Malaga, Spain

Aboard

Star Legend

From

Malaga, Spain

Published prices from

$3,304

per person*

taxes & fees included

Historic El Morro fortress overlooking the ocean in San Juan, Puerto Rico.
Windstar

7-night San Juan & The Virgin Islands Cruise From San Juan, Puerto Rico

Aboard

Star Pride

From

San Juan, Puerto Rico

Published prices from

$2,548

per person*

taxes & fees included

Rocky beach and palm trees in Barbados.
Windstar

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

Aboard

Wind Star

From

Bridgetown, Barbados

Colorful colonial balconies in Cartagena.
Windstar

11-night Colombian & Southern Caribbean Coastlines Cruise From Bridgetown, Barbados

Aboard

Wind Star

From

Bridgetown, Barbados

Published prices from

$6,851

per person*

taxes & fees included

A view of Pigeon Island National Landmark, St. Lucia, showing a lush, green peninsula jutting out into the ocean with waves crashing on the rocks.
Windstar

15-night Star Collector: Captivating Caribbean Cruise From Bridgetown, Barbados

Aboard

Star Legend

From

Bridgetown, Barbados

Published prices from

$4,439

per person*

taxes & fees included

A vibrant panoramic view of Castries, St. Lucia, with colorful buildings nestled along the harbor and lush green hills in the background under a blue sky with white clouds.
Windstar

7-night Jewels Of The Windward Islands Cruise From Bridgetown, Barbados

Aboard

Star Legend

From

Bridgetown, Barbados

Published prices from

$1,942

per person*

taxes & fees included

A breathtaking aerial view of the iconic Pitons, two majestic volcanic peaks, rising from the turquoise waters of the Caribbean Sea on the island of St. Lucia, with a small bay and sailboats.
Windstar

16-night Star Collector: Windward Islands & Spanish New World Cruise From Bridgetown, Barbados

Aboard

Star Legend

From

Bridgetown, Barbados

Published prices from

$4,414

per person*

taxes & fees included

A breathtaking tropical beach on Mayreau Island, Grenadines, with white sand, tall palm trees, and turquoise water under a perfectly blue sky.
Windstar

8-night Windward Ways & Tobago Cays Cruise From Bridgetown, Barbados

Aboard

Star Legend

From

Bridgetown, Barbados

Published prices from

$2,820

per person*

taxes & fees included

An aerial view of Road Bay, Anguilla, showing a pristine white sand beach, lush green vegetation, and the stunningly clear turquoise water of the Caribbean Sea.
Windstar

21-night Star Collector: Hearty Ports & Rum Punches - A Transatlantic Crossing Cruise From Lisbon, Portugal

Aboard

Wind Surf

From

Lisbon, Portugal

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.
Windstar

8-night Panama Canal, Cartagena, San Blas Islands & More Cruise From Oranjestad, Aruba, Caribbean

Aboard

Star Legend

From

Oranjestad, Aruba, Caribbean

Published prices from

$2,886

per person*

taxes & fees included

Lush rainforest and beach in Costa Rica.
Windstar

16-night Star Collector: Latin America Explorer Cruise From Oranjestad, Aruba, Caribbean

Aboard

Star Legend

From

Oranjestad, Aruba, Caribbean

Published prices from

$5,719

per person*

taxes & fees included

Cupecoy Beach with white resort buildings, St. Maarten.
Windstar

7-night Beach Fun & Sun: A Remote Caribbean Getaway Cruise From Philipsburg, St. Maarten, The Netherlands

Aboard

Wind Surf

From

Philipsburg, St. Maarten, The Netherlands

Published prices from

$2,623

per person*

taxes & fees included

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.
Windstar

14-night Star Collector: Caribbean Explorations Cruise From Philipsburg, St. Maarten, The Netherlands

Aboard

Wind Surf

From

Philipsburg, St. Maarten, The Netherlands

Published prices from

$4,208

per person*

taxes & fees included

A breathtaking panoramic view of Charlotte Amalie harbor in St. Thomas, with a cruise ship anchored in the bay, surrounded by rolling green hills and a colorful sunset.
Windstar

7-night Classic Caribbean Cruise From Philipsburg, St. Maarten, The Netherlands

Aboard

Wind Surf

From

Philipsburg, St. Maarten, The Netherlands

Published prices from

$2,432

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.
Windstar

13-night Latin America Explorer Cruise From Puerto Caldera, Costa Rica

Aboard

Star Legend

From

Puerto Caldera, Costa Rica

Published prices from

$5,800

per person*

taxes & fees included

Colorful colonial balconies in Cartagena.
Windstar

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

Aboard

Star Legend

From

Fuerte Amador, Panama

Published prices from

$3,066

per person*

taxes & fees included

A breathtaking aerial view of the iconic Pitons, two majestic volcanic peaks, rising from the turquoise waters of the Caribbean Sea on the island of St. Lucia, with a small bay and sailboats.
Windstar

14-night Star Collector: Windward Islands & Spanish New World Cruise From Fuerte Amador, Panama

Aboard

Star Legend

From

Fuerte Amador, Panama

Published prices from

$8,290

per person*

taxes & fees included

A stunning panoramic view of Rodney Bay on the island of St. Lucia, showing a bustling harbor filled with sailboats, a colorful town, and lush green hills under a bright blue, cloudy sky.
Windstar

8-night Windward Ways & Tobago Cays Cruise From Oranjestad, Aruba, Caribbean

Aboard

Star Legend

From

Oranjestad, Aruba, Caribbean

Published prices from

$5,820

per person*

taxes & fees included

A beautiful Porto Santo beach landscape with a long stretch of golden sand, a wicker bench, a wooden fence, and the distinctive mountains of Madeira in the background.
Windstar

15-night Ocean Crossings Cruise From Bridgetown, Barbados

Aboard

Star Legend

From

Bridgetown, Barbados

Published prices from

$2,796

per person*

taxes & fees included

A scenic view of the iconic Plaza de España in Seville, Spain, featuring its grand arcade of arches and columns, a main building with a clock tower, and a bright blue sky.
Windstar

23-night Star Collector Cruise: Spanish Shores Transatlantic Crossing From Bridgetown, Barbados

Aboard

Star Legend

From

Bridgetown, Barbados

Published prices from

$5,567

per person*

taxes & fees included

A beautiful panoramic shot from a garden in Funchal, Madeira, Portugal, showcasing meticulously manicured flower beds in geometric patterns with the city and the Atlantic Ocean in the background.
Windstar

15-night Ocean Crossings Cruise From Philipsburg, St. Maarten, The Netherlands

Aboard

Wind Surf

From

Philipsburg, St. Maarten, The Netherlands

Published prices from

$3,030

per person*

taxes & fees included

Historic Halifax waterfront buildings.
Windstar

25-night Star Collector: Autumn In Newfoundland And New England Cruise From Boston, Massachusetts

Aboard

Star Pride

From

Boston, Massachusetts

Published prices from

$14,478

per person*

taxes & fees included

Historic El Morro fortress overlooking the ocean in San Juan, Puerto Rico.
Windstar

21-night Star Collector: Fall Leaves & Caribbean Breezes Cruise From Montreal, Quebec

Aboard

Star Pride

From

Montreal, Quebec

Published prices from

$7,187

per person*

taxes & fees included

A panoramic view of Gustavia, Saint Barthélemy, featuring a bay filled with luxury yachts and sailboats, framed by lush, green hillsides dotted with houses.
Windstar

17-night Star Collector Cruise: Bermuda & Caribbean Island Explorer From Boston, Massachusetts

Aboard

Star Pride

From

Boston, Massachusetts

Published prices from

$4,926

per person*

taxes & fees included

A panoramic view of Gustavia, Saint Barthélemy, featuring a bay filled with luxury yachts and sailboats, framed by lush, green hillsides dotted with houses.
Windstar

10-night Bermuda Bliss Cruise From Boston, Massachusetts

Aboard

Star Pride

From

Boston, Massachusetts

Published prices from

$3,027

per person*

taxes & fees included

An aerial view of the colorful waterfront of St. George's, Grenada, with the town's buildings nestled on a hillside and a long, rocky breakwater extending into the calm, turquoise water.
Windstar

21-night Star Collector Cruise: Windward Islands, Spanish Cities & Costa Rica From San Juan, Puerto Rico

Aboard

Star Pride

From

San Juan, Puerto Rico

Published prices from

$7,397

per person*

taxes & fees included

A high-angle view of the bustling harbor of Marigot, St. Martin, with boats and yachts docked along the coast and colorful buildings nestled against the green hills.
Windstar

14-night Star Collector Cruise: Caribbean Islands & Colombian Coast Discovery From San Juan, Puerto Rico

Aboard

Star Pride

From

San Juan, Puerto Rico

Published prices from

$4,939

per person*

taxes & fees included

This is a scenic image of a tropical beach in Santo Domingo, with multiple colorful fishing boats resting on the sandy shore, tall palm trees, and the calm turquoise sea under a bright, clear sky.
Windstar

7-night The Spanish Main: Rise Of The New World Cruise From San Juan, Puerto Rico

Aboard

Star Pride

From

San Juan, Puerto Rico

Published prices from

$3,081

per person*

taxes & fees included

Historic El Morro fortress overlooking the ocean in San Juan, Puerto Rico.
Windstar

14-night Star Collector: Coffee, Canal & Callaloo: Central America, Colombia & The Caribbean Cruise From San Juan, Puerto Rico

Aboard

Star Pride

From

San Juan, Puerto Rico

Published prices from

$4,930

per person*

taxes & fees included

A panoramic view of Gustavia, Saint Barthélemy, featuring a bay filled with luxury yachts and sailboats, framed by lush, green hillsides dotted with houses.
Windstar

7-night Beach Fun & Sun: A Remote Caribbean Getaway From Philipsburg, St. Maarten, The Netherlands

Aboard

Wind Surf

From

Philipsburg, St. Maarten, The Netherlands

Published prices from

$2,623

per person*

taxes & fees included

Belém Tower on Tagus River.
Windstar

14-night Ocean Crossings Cruise From Lisbon, Portugal

Aboard

Star Legend

From

Lisbon, Portugal

Published prices from

$7,784

per person*

taxes & fees included

Historic El Morro fortress overlooking the ocean in San Juan, Puerto Rico.
Windstar

21-night Star Collector Cruise: Atlantic Crossing To The Virgin Islands From Lisbon, Portugal

Aboard

Star Legend

From

Lisbon, Portugal

Published prices from

$11,676

per person*

taxes & fees included

A snorkeler swims in the turquoise waters of the Baths National Park on Virgin Gorda, surrounded by massive granite boulders and palm trees.
Windstar

7-night San Juan & The Virgin Islands Cruise From San Juan, Puerto Rico

Aboard

Star Legend

From

San Juan, Puerto Rico

Published prices from

$2,723

per person*

taxes & fees included

A breathtaking panoramic view of Cruz Bay, St. John, showcasing a vibrant coastal town with white-sand beaches, clear turquoise waters, and numerous boats in the harbor.
Windstar

14-night Star Collector Cruise: Lovely Leewards From San Juan, Puerto Rico

Aboard

Star Legend

From

San Juan, Puerto Rico

Published prices from

$4,350

per person*

taxes & fees included

A high-angle view of the bustling harbor of Marigot, St. Martin, with boats and yachts docked along the coast and colorful buildings nestled against the green hills.
Windstar

7-night Windward Islands Surf & Sunsets Cruise From San Juan, Puerto Rico

Aboard

Star Legend

From

San Juan, Puerto Rico

Published prices from

$2,691

per person*

taxes & fees included

A close-up shot of two cougars, or pumas, resting on a rocky ledge. The cougar in the foreground looks directly at the camera, its tawny-colored face and alert eyes focused, while the other cougar is curled up and resting behind it.
Windstar

21-night Star Collector Cruise: Costa Rica, Panama & Aruba From Puerto Caldera, Costa Rica

Aboard

Star Pride

From

Puerto Caldera, Costa Rica

Published prices from

$6,927

per person*

taxes & fees included

A close-up shot of two cougars, or pumas, resting on a rocky ledge. The cougar in the foreground looks directly at the camera, its tawny-colored face and alert eyes focused, while the other cougar is curled up and resting behind it.
Windstar

14-night Star Collector Cruise: Latin America Explorer From Puerto Caldera, Costa Rica

Aboard

Star Pride

From

Puerto Caldera, Costa Rica

Published prices from

$5,166

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.
Windstar

22-night Star Collector Cruise: Caribbean Charms To Iberian Shores From San Juan, Puerto Rico

Aboard

Star Legend

From

San Juan, Puerto Rico

Published prices from

$2,451

per person*

taxes & fees included

An aerial view of the bustling city of Balboa, Panama, with a scenic coastal road alongside a marina and tall modern skyscrapers in the background.
Windstar

14-night Star Collector Cruise: Panama, Aruba & The British Virgin Islands From Balboa, Panama

Aboard

Star Pride

From

Balboa, Panama

Published prices from

$5,073

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 From Balboa, Panama

Aboard

Star Pride

From

Balboa, Panama

Published prices from

$2,676

per person*

taxes & fees included

An aerial view of Agadir, Morocco, showcasing the city's long sandy beach and curving coastline, with a busy marina and port in the foreground.
Windstar

15-night Ocean Crossings Cruise From San Juan, Puerto Rico

Aboard

Star Legend

From

San Juan, Puerto Rico

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.
Windstar

21-night Star Collector Cruise: Caribbean Collection: ABC, BVI & The Windwards From Oranjestad, Aruba, Caribbean

Aboard

Star Pride

From

Oranjestad, Aruba, Caribbean

Published prices from

$7,097

per person*

taxes & fees included

A scenic landscape view of Admiralty Bay in Bequia, St. Vincent and the Grenadines, with dozens of sailboats moored on the vibrant turquoise water, surrounded by lush green hills.
Windstar

14-night Star Collector Cruise: Windward Islands, ABC Islands & The Virgin Islands From Oranjestad, Aruba, Caribbean

Aboard

Star Pride

From

Oranjestad, Aruba, Caribbean

Published prices from

$5,046

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.
Windstar

7-night Island Trails Cruise: Aruba To The Virgin Islands From Oranjestad, Aruba, Caribbean

Aboard

Star Pride

From

Oranjestad, Aruba, Caribbean

Published prices from

$3,559

per person*

taxes & fees included

A scenic landscape view of Admiralty Bay in Bequia, St. Vincent and the Grenadines, with dozens of sailboats moored on the vibrant turquoise water, surrounded by lush green hills.
Windstar

23-night Star Collector Cruise: Tropical Horizons To Historic Amsterdam From San Juan, Puerto Rico

Aboard

Star Pride

From

San Juan, Puerto Rico

Published prices from

$4,655

per person*

taxes & fees included

Tulip fields with traditional windmills, showcasing the beauty of the Netherlands in springtime.
Windstar

16-night Ocean Crossings Cruise From San Juan, Puerto Rico

Aboard

Star Pride

From

San Juan, Puerto Rico

Published prices from

$2,760

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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