Southern Caribbean Cruises on Windstar

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

Aboard

Star Seeker

From

San Juan, Puerto Rico

2 Sailings

Feb 27 - Mar 13, 2026

2 Sailings

Feb 27 - Mar 13, 2026

Published prices from

$5,733

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.

14-night Star Collector: Lovely Leewards Cruise

San Juan

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Aboard

Star Seeker

From

San Juan, Puerto Rico

2 Sailings

Feb 27 - Mar 6, 2026

2 Sailings

Feb 27 - Mar 6, 2026

Cupecoy Beach with white resort buildings, St. Maarten.

7-night Classic Caribbean Cruise

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

Aboard

Wind Surf

From

Philipsburg, St. Maarten, The Netherlands

10 Sailings

Feb 28, 2026 - Nov 28, 2027

10 Sailings

Feb 28, 2026 - Nov 28, 2027

Published prices from

$2,851

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.

15-night Star Collector: Antilles Adventure Cruise

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Aboard

Wind Spirit

From

Philipsburg, St. Maarten, The Netherlands

1 Sailing

Feb 28, 2026

1 Sailing

Feb 28, 2026

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

14-night Star Collector: Caribbean Explorations Cruise

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Aboard

Wind Surf

From

Philipsburg, St. Maarten, The Netherlands

16 Sailings

Feb 28, 2026 - Mar 13, 2027

16 Sailings

Feb 28, 2026 - Mar 13, 2027

Published prices from

$5,519

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.

7-night Lush & Lovely Islands of the Lesser Antilles Cruise

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

Aboard

Wind Spirit

From

Philipsburg, St. Maarten, The Netherlands

1 Sailing

Feb 28, 2026

1 Sailing

Feb 28, 2026

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.

7-night Jewels of the Windward Islands Cruise

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Aboard

Wind Spirit

From

Bridgetown, Barbados

1 Sailing

Mar 7, 2026

1 Sailing

Mar 7, 2026

14-night Star Collector: Captivating Caribbean Cruise

Up to $500 FREE Onboard Credit*+ 2 more offers

Aboard

Wind Spirit

From

Bridgetown, Barbados

1 Sailing

Mar 7, 2026

1 Sailing

Mar 7, 2026

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.

TCW EXCLUSIVE

6-night Panama’s Pristine Caribbean Cruise

Aboard

Star Pride

From

Colon, Panama

1 Sailing

Mar 9, 2026

1 Sailing

Mar 9, 2026

Published prices from

$3,279

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

7-night Windward Island Delights Cruise

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Aboard

Wind Spirit

From

Bridgetown, Barbados

1 Sailing

Mar 15, 2026

1 Sailing

Mar 15, 2026

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.

7-night Windward Ways and Tobago Cays Cruise

Aboard

Star Pride

From

Oranjestad, Aruba, Caribbean

1 Sailing

Mar 15, 2026

1 Sailing

Mar 15, 2026

Published prices from

$3,779

per person*

taxes & fees included

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

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

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

Aboard

Wind Spirit

From

Bridgetown, Barbados

1 Sailing

Mar 21, 2026

1 Sailing

Mar 21, 2026

7-night Jewels of the Windward Islands Cruise

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

Aboard

Wind Spirit

From

Bridgetown, Barbados

1 Sailing

Mar 21, 2026

1 Sailing

Mar 21, 2026

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

16-night Ocean Crossings Cruise

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

Amsterdam

Aboard

Star Pride

From

Bridgetown, Barbados

1 Sailing

Mar 22, 2026

1 Sailing

Mar 22, 2026

Published prices from

$4,014

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.

10-night Gems Of The Leeward Islands Cruise

Aboard

Star Seeker

From

San Juan, Puerto Rico

1 Sailing

Mar 27, 2026

1 Sailing

Mar 27, 2026

Published prices from

$6,757

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

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

Aboard

Star Seeker

From

San Juan, Puerto Rico

1 Sailing

Mar 27, 2026

1 Sailing

Mar 27, 2026

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

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

Aboard

Star Seeker

From

San Juan, Puerto Rico

1 Sailing

Mar 27, 2026

1 Sailing

Mar 27, 2026

Colorful colonial balconies in Cartagena.

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

17-night Star Collector: Seeking The Antilles Cruise

Aboard

Star Seeker

From

San Juan, Puerto Rico

1 Sailing

Mar 27, 2026

1 Sailing

Mar 27, 2026

Published prices from

$12,244

per person*

taxes & fees included

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

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

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

Aboard

Wind Spirit

From

Bridgetown, Barbados

1 Sailing

Mar 28, 2026

1 Sailing

Mar 28, 2026

Published prices from

$6,590

per person*

taxes & fees included

15-night Ocean Crossings Cruise

Up to $500 FREE Onboard Credit*+ 2 more offers

Aboard

Wind Spirit

From

Bridgetown, Barbados

1 Sailing

Mar 28, 2026

1 Sailing

Mar 28, 2026

A vibrant orange and red sunset over the tranquil harbor in Sydney, Nova Scotia, with the setting sun reflecting on the water.

TCW EXCLUSIVE

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

Boston

Rockland

Portland

Halifax (Nova Scotia)

Sydney (Nova Scotia)

+13 more

Aboard

Star Pride

From

Boston, Massachusetts

1 Sailing

Sep 14, 2026

1 Sailing

Sep 14, 2026

Published prices from

$18,525

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

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

Montreal

Quebec City

Baie-Comeau (Comeau Bay)

Cap-aux-Meules

St. Pierre and Miquelon

+13 more

Aboard

Star Pride

From

Montreal, Quebec

1 Sailing

Sep 25, 2026

1 Sailing

Sep 25, 2026

Published prices from

$18,425

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

14-night Quebec And Newfoundland Adventure Cruise

Montreal

Quebec City

Baie-Comeau (Comeau Bay)

Cap-aux-Meules

St. Pierre and Miquelon

+7 more

Aboard

Star Pride

From

Montreal, Quebec

2 Sailings

Sep 25, 2026 - Sep 27, 2027

2 Sailings

Sep 25, 2026 - Sep 27, 2027

Published prices from

$6,669

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

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

Aboard

Star Legend

From

Istanbul, Turkey

1 Sailing

Oct 19, 2026

1 Sailing

Oct 19, 2026

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

11-night Gems Of The Leeward Islands Cruise

Aboard

Star Pride

From

San Juan, Puerto Rico

1 Sailing

Oct 28, 2026

1 Sailing

Oct 28, 2026

Published prices from

$4,257

per person*

taxes & fees included

Up to $500 FREE Onboard Credit*+ 2 more offers

TCW EXCLUSIVE

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

Barcelona

Barcelona (Tarragona)

Aboard

Wind Star

From

Barcelona, Spain

1 Sailing

Oct 31, 2026

1 Sailing

Oct 31, 2026

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

14-night Star Collector: Lovely Leewards Cruise

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

+8 more

Aboard

Star Pride

From

San Juan, Puerto Rico

14 Sailings

Nov 8, 2026 - Mar 20, 2028

14 Sailings

Nov 8, 2026 - Mar 20, 2028

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.

7-night Windward Islands Surf & Sunsets Cruise

Aboard

Star Pride

From

San Juan, Puerto Rico

9 Sailings

Nov 8, 2026 - Mar 27, 2028

9 Sailings

Nov 8, 2026 - Mar 27, 2028

Published prices from

$2,930

per person*

taxes & fees included

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

14-night Ocean Crossings Cruise

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

Aboard

Wind Star

From

Lisbon, Portugal

1 Sailing

Nov 10, 2026

1 Sailing

Nov 10, 2026

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.

25-night Star Collector: Southern Caribbean Thanksgiving Jubilee Cruise

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

Aboard

Wind Star

From

Lisbon, Portugal

1 Sailing

Nov 10, 2026

1 Sailing

Nov 10, 2026

13-night Ocean Crossings Cruise

Funchal (Madeira)

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

Aboard

Star Legend

From

Lisbon, Portugal

1 Sailing

Nov 14, 2026

1 Sailing

Nov 14, 2026

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.

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

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

Aboard

Wind Star

From

Bridgetown, Barbados

1 Sailing

Nov 24, 2026

1 Sailing

Nov 24, 2026

11-night Colombian & Southern Caribbean Coastlines Cruise

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

Aboard

Wind Star

From

Bridgetown, Barbados

1 Sailing

Nov 24, 2026

1 Sailing

Nov 24, 2026

Published prices from

$6,030

per person*

taxes & fees included

15-night Star Collector: Captivating Caribbean Cruise

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

Aboard

Star Legend

From

Bridgetown, Barbados

1 Sailing

Nov 27, 2026

1 Sailing

Nov 27, 2026

Published prices from

$5,658

per person*

taxes & fees included

7-night Jewels Of The Windward Islands Cruise

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

Aboard

Star Legend

From

Bridgetown, Barbados

1 Sailing

Nov 27, 2026

1 Sailing

Nov 27, 2026

Published prices from

$3,138

per person*

taxes & fees included

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

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

Aboard

Star Legend

From

Bridgetown, Barbados

1 Sailing

Dec 4, 2026

1 Sailing

Dec 4, 2026

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.

8-night Windward Ways & Tobago Cays Cruise