Windstar

Caribbean Cruises on Windstar

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

Upcoming Caribbean Cruises on Windstar

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

6-night Panama’s Pristine Caribbean Cruise

Aboard

Star Pride

From

Colon, Panama

Published prices from

$3,279

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.
FREE All-Inclusive Upgrade + FREE Hotel Stay + up to $2,300 Onboard Credit*+ 1 more offer
Windstar

7-night Windward Islands Surf & Sunsets Cruise

Aboard

Star Seeker

From

San Juan, Puerto Rico

Published prices from

$5,733

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.
FREE All-Inclusive Upgrade + FREE Hotel Stay + up to $2,300 Onboard Credit*+ 1 more offer
Windstar

7-night Beach Fun & Sun: A Remote Caribbean Getaway Cruise

Aboard

Wind Surf

From

Philipsburg, St. Maarten, The Netherlands

Published prices from

$3,267

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.
FREE All-Inclusive Upgrade + FREE Hotel Stay + up to $2,300 Onboard Credit*+ 1 more offer
Windstar

14-night Star Collector: Caribbean Explorations Cruise

Aboard

Wind Surf

From

Philipsburg, St. Maarten, The Netherlands

Published prices from

$5,519

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.
FREE All-Inclusive Upgrade + FREE Hotel Stay + up to $2,300 Onboard Credit*+ 1 more offer
Windstar

7-night Windward Island Delights Cruise

Aboard

Wind Spirit

From

Bridgetown, Barbados

Published prices from

$4,216

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 + FREE Hotel Stay + up to $2,300 Onboard Credit*+ 1 more offer
Windstar

7-night Windward Ways and Tobago Cays Cruise

Aboard

Star Pride

From

Oranjestad, Aruba, Caribbean

Published prices from

$3,779

per person*

taxes & fees included

A scenic view of Forte de São João Baptista, a fortress built on a rocky islet in the Berlengas Archipelago, connected by a stone causeway over turquoise water.
FREE All-Inclusive Upgrade + FREE Hotel Stay + up to $2,300 Onboard Credit*+ 1 more offer
Windstar

7-night 2026 President’s Mystery Cruise

Aboard

Star Seeker

From

San Juan, Puerto Rico

Rocky beach and palm trees in Barbados.
FREE All-Inclusive Upgrade + FREE Hotel Stay + up to $2,300 Onboard Credit*+ 1 more offer
Windstar

22-night Star Collector: Caribbean Beats & Transatlantic Treats Cruise

Aboard

Wind Spirit

From

Bridgetown, Barbados

Rocky beach and palm trees in Barbados.
FREE All-Inclusive Upgrade + FREE Hotel Stay + up to $2,300 Onboard Credit*+ 1 more offer
Windstar

7-night Jewels of the Windward Islands Cruise

Aboard

Wind Spirit

From

Bridgetown, Barbados

Cupecoy Beach with white resort buildings, St. Maarten.
FREE All-Inclusive Upgrade + FREE Hotel Stay + up to $2,300 Onboard Credit*+ 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

Tulip fields with traditional windmills, showcasing the beauty of the Netherlands in springtime.
FREE All-Inclusive Upgrade + FREE Hotel Stay + up to $2,300 Onboard Credit*+ 1 more offer
Windstar

16-night Ocean Crossings Cruise

Aboard

Star Pride

From

Bridgetown, Barbados

Published prices from

$4,014

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 + FREE Hotel Stay + up to $2,300 Onboard Credit*+ 1 more offer
Windstar

49-night Star Collector: Grand Caribbean & Americas Explorer Cruise

Aboard

Star Seeker

From

San Juan, Puerto Rico

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.
FREE All-Inclusive Upgrade + FREE Hotel Stay + up to $2,300 Onboard Credit*+ 1 more offer
Windstar

10-night Gems Of The Leeward Islands Cruise

Aboard

Star Seeker

From

San Juan, Puerto Rico

Published prices from

$6,757

per person*

taxes & fees included

Colorful colonial balconies in Cartagena.
FREE All-Inclusive Upgrade + FREE Hotel Stay + up to $2,300 Onboard Credit*+ 1 more offer
Windstar

17-night Star Collector: Seeking The Antilles Cruise

Aboard

Star Seeker

From

San Juan, Puerto Rico

Published prices from

$12,244

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.
FREE All-Inclusive Upgrade + FREE Hotel Stay + up to $2,300 Onboard Credit*+ 1 more offer
Windstar

24-night Star Collector: Historic Caribbean: Legendary Islands, Colombia And Panama Cruise

Aboard

Star Seeker

From

San Juan, Puerto Rico

Alcazaba fortress in Malaga.
FREE All-Inclusive Upgrade + FREE Hotel Stay + up to $2,300 Onboard Credit*+ 1 more offer
Windstar

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

Aboard

Wind Spirit

From

Bridgetown, Barbados

Published prices from

$6,590

per person*

taxes & fees included

Rocky beach and palm trees in Barbados.
FREE All-Inclusive Upgrade + FREE Hotel Stay + up to $2,300 Onboard Credit*+ 1 more offer
Windstar

15-night Ocean Crossings Cruise

Aboard

Wind Spirit

From

Bridgetown, Barbados

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 + FREE Hotel Stay + up to $2,300 Onboard Credit*+ 2 more offers
Windstar

6-night Beach Fun & Sun: A Remote Caribbean Getaway Cruise

Aboard

Wind Surf

From

Philipsburg, St. Maarten, The Netherlands

Published prices from

$4,567

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.
FREE All-Inclusive Upgrade + FREE Hotel Stay + up to $2,300 Onboard Credit*+ 1 more offer
Windstar

21-night Star Collector: Spectacular Transatlantic Journey: Caribbean To The Azores Cruise

Aboard

Wind Surf

From

Philipsburg, St. Maarten, The Netherlands

Published prices from

$6,894

per person*

taxes & fees included

Cupecoy Beach with white resort buildings, St. Maarten.
FREE All-Inclusive Upgrade + FREE Hotel Stay + up to $2,300 Onboard Credit*+ 1 more offer
Windstar

14-night Ocean Crossings + Ponta Delgada, Azores Cruise

Aboard

Wind Surf

From

Philipsburg, St. Maarten, The Netherlands

Published prices from

$3,426

per person*

taxes & fees included

A historic fortress, the Castle of La Calahorra, stands on a hilltop overlooking a town with white-washed houses below, under a blue sky with scattered clouds in Almería, Spain.
FREE All-Inclusive Upgrade + FREE Hotel Stay + up to $2,300 Onboard Credit*+ 1 more offer
Windstar

22-night Star Collector: Atlantic Interludes & Iberian Indulgences Cruise

Aboard

Wind Surf

From

Philipsburg, St. Maarten, The Netherlands

Published prices from

$7,148

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.
FREE All-Inclusive Upgrade + FREE Hotel Stay + up to $2,300 Onboard Credit*+ 1 more offer
Windstar

22-night Star Collector Cruise: Central American Explorations Via The Panama Canal

Aboard

Star Seeker

From

San Juan, Puerto Rico

Colorful colonial balconies in Cartagena.
FREE All-Inclusive Upgrade + FREE Hotel Stay + up to $2,300 Onboard Credit*+ 1 more offer
Windstar

7-night New World Caribbean Trio Cruise

Aboard

Star Seeker

From

San Juan, Puerto Rico

Published prices from

$4,826

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 + FREE Hotel Stay + up to $2,300 Onboard Credit*+ 1 more offer
Windstar

14-night Star Collector: Rainforest Refuges Of Panama & Costa Rica Via The Panama Canal Cruise

Aboard

Star Seeker

From

San Juan, Puerto Rico

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

$16,865

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 + FREE Hotel Stay + up to $2,300 Onboard Credit*+ 1 more offer
Windstar

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

Aboard

Star Pride

From

Montreal, Quebec

Published prices from

$16,765

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 + FREE Hotel Stay + up to $2,300 Onboard Credit*+ 1 more offer
Windstar

14-night Quebec And Newfoundland Adventure Cruise

Aboard

Star Pride

From

Montreal, Quebec

Published prices from

$6,669

per person*

taxes & fees included

Historic Acorn Street in Boston.
FREE All-Inclusive Upgrade + FREE Hotel Stay + up to $2,300 Onboard Credit*+ 1 more offer
Windstar

19-night Star Collector: Fall Leaves & Caribbean Breezes Cruise

Aboard

Star Pride

From

Montreal, Quebec

Published prices from

$8,922

per person*

taxes & fees included

Blue Mosque and historic Istanbul skyline with Bosphorus Strait.
FREE All-Inclusive Upgrade + FREE Hotel Stay + up to $2,300 Onboard Credit*+ 1 more offer
Windstar

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

Aboard

Star Legend

From

Istanbul, Turkey

Historic El Morro fortress overlooking the ocean in San Juan, Puerto Rico.
Up to $500 FREE Onboard Credit*+ 2 more offers
TCW EXCLUSIVE
Windstar

8-night Bermuda Bliss Cruise

Aboard

Star Pride

From

Boston, Massachusetts

Published prices from

$2,926

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.
FREE All-Inclusive Upgrade + FREE Hotel Stay + up to $2,300 Onboard Credit*+ 1 more offer
Windstar

11-night Gems Of The Leeward Islands Cruise

Aboard

Star Pride

From

San Juan, Puerto Rico

Published prices from

$9,157

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

Published prices from

$6,990

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.
FREE All-Inclusive Upgrade + FREE Hotel Stay + up to $2,300 Onboard Credit*+ 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 + FREE Hotel Stay + up to $2,300 Onboard Credit*+ 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 + FREE Hotel Stay + up to $2,300 Onboard Credit*+ 1 more offer
Windstar

14-night Ocean Crossings Cruise

Aboard

Wind Star

From

Lisbon, Portugal

Published prices from

$3,725

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 + FREE Hotel Stay + up to $2,300 Onboard Credit*+ 1 more offer
Windstar

25-night Star Collector: Southern Caribbean Thanksgiving Jubilee Cruise

Aboard

Wind Star

From

Lisbon, Portugal

Published prices from

$9,056

per person*

taxes & fees included

Belém Tower on Tagus River.
FREE All-Inclusive Upgrade + FREE Hotel Stay + up to $2,300 Onboard Credit*+ 1 more offer
Windstar

13-night Ocean Crossings Cruise

Aboard

Star Legend

From

Lisbon, Portugal

A snorkeler swims in the turquoise waters of the Baths National Park on Virgin Gorda, surrounded by massive granite boulders and palm trees.
FREE All-Inclusive Upgrade + FREE Hotel Stay + up to $2,300 Onboard Credit*+ 1 more offer
Windstar

7-night San Juan & The Virgin Islands Cruise

Aboard

Star Pride

From

San Juan, Puerto Rico

Published prices from

$2,862

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 + FREE Hotel Stay + up to $2,300 Onboard Credit*+ 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

Published prices from

$10,700

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 + FREE Hotel Stay + up to $2,300 Onboard Credit*+ 1 more offer
Windstar

11-night Colombian & Southern Caribbean Coastlines Cruise

Aboard

Wind Star

From

Bridgetown, Barbados

Published prices from

$6,030

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 + FREE Hotel Stay + up to $2,300 Onboard Credit*+ 1 more offer
Windstar

15-night Star Collector: Captivating Caribbean Cruise

Aboard

Star Legend

From

Bridgetown, Barbados

Published prices from

$5,658

per person*

taxes & fees included

Rocky beach and palm trees in Barbados.
FREE All-Inclusive Upgrade + FREE Hotel Stay + up to $2,300 Onboard Credit*+ 1 more offer
Windstar

7-night Jewels Of The Windward Islands Cruise

Aboard

Star Legend

From

Bridgetown, Barbados

Published prices from

$3,138

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 + FREE Hotel Stay + up to $2,300 Onboard Credit*+ 1 more offer
Windstar

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

Aboard

Star Legend

From

Bridgetown, Barbados

Published prices from

$5,811

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 + FREE Hotel Stay + up to $2,300 Onboard Credit*+ 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 captivating half-underwater, half-above-water shot of a person snorkeling in the vibrant turquoise waters of the British Virgin Islands with stunning rock formations and palm trees visible above the waterline.
FREE All-Inclusive Upgrade + FREE Hotel Stay + up to $2,300 Onboard Credit*+ 1 more offer
Windstar

21-night Star Collector: Hearty Ports & Rum Punches - A Transatlantic Crossing Cruise

Aboard

Wind Surf

From

Lisbon, Portugal

An aerial view of the colorful waterfront of St. John's, Antigua, with a long pier extending into the calm, blue sea and the town's charming buildings and marina in the background.
FREE All-Inclusive Upgrade + FREE Hotel Stay + up to $2,300 Onboard Credit*+ 1 more offer
Windstar

14-night Ocean Crossings Cruise

Aboard

Wind Surf

From

Lisbon, Portugal

A cruise ship navigating through the Gatun Locks of the Panama Canal, an important navigational route and popular tourist destination.
FREE All-Inclusive Upgrade + FREE Hotel Stay + up to $2,300 Onboard Credit*+ 1 more offer
Windstar

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

Aboard

Star Legend

From

Oranjestad, Aruba, Caribbean

Published prices from

$3,565

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 + FREE Hotel Stay + up to $2,300 Onboard Credit*+ 1 more offer
Windstar

16-night Star Collector: Latin America Explorer Cruise

Aboard

Star Legend

From

Oranjestad, Aruba, Caribbean

Published prices from

$5,677

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.
FREE All-Inclusive Upgrade + FREE Hotel Stay + up to $2,300 Onboard Credit*+ 1 more offer
Windstar

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

Aboard

Star Legend

From

Balboa, Panama

Published prices from

$6,685

per person*

taxes & fees included

Cupecoy Beach with white resort buildings, St. Maarten.
FREE All-Inclusive Upgrade + FREE Hotel Stay + up to $2,300 Onboard Credit*
Windstar

15-night Ocean Crossings Cruise

Aboard

Wind Surf

From

Philipsburg, St. Maarten, The Netherlands

Published prices from

$4,029

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

Notre-Dame Basilica in Montreal.
Windstar

21-night Star Collector: Fall Leaves & Caribbean Breezes Cruise

Aboard

Star Pride

From

Montreal, Quebec

Published prices from

$7,122

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

10-night Bermuda Bliss Cruise

Aboard

Star Pride

From

Boston, Massachusetts

Published prices from

$3,026

per person*

taxes & fees included

Colorful colonial balconies in Cartagena.
Windstar

7-night The Spanish Main: Rise Of The New World Cruise

Aboard

Star Pride

From

San Juan, Puerto Rico

Published prices from

$2,835

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: Coffee, Canal & Callaloo: Central America, Colombia & The Caribbean Cruise

Aboard

Star Pride

From

San Juan, Puerto Rico

Published prices from

$4,993

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.

More to Explore

Cruise Lines

Silversea Cruises

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Norwegian Cruise Line

Oceania Cruises

Carnival Cruise Line

Destinations

Africa

Asia

Transatlantic

South America

Egypt

Ports

Santa Cruz de Tenerife, Canary Islands

Engelhartszell, Austria

Kriens, Switzerland

Eze, Cote d' Azur

Elba, Italy

Cruise Ships

Viking Lofn

AmaLilia

AmaMora

AmaLucia

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