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A beautiful panoramic view of Roseau, Dominica, with a colorful town nestled between the deep blue Caribbean Sea and a backdrop of lush green, volcanic mountains.
FREE All-Inclusive Upgrade + FREE Hotel Stay + up to $2,000 Onboard Credit*+ 1 more offer
Windstar

15-night Star Collector: Merry Christmas & Happy New Years From The Caribbean Cruise

Aboard

Wind Spirit

From

Oranjestad, Aruba, Caribbean

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.
FREE All-Inclusive Upgrade + FREE Hotel Stay + up to $2,000 Onboard Credit*+ 1 more offer
Windstar

8-night An ABC Christmas Cruise

Aboard

Wind Spirit

From

Oranjestad, Aruba, Caribbean

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 $2,000 Onboard Credit*+ 1 more offer
Windstar

28-night Star Collector: The Best Of The Windward & Leeward Isles Cruise

Aboard

Wind Surf

From

Philipsburg, St. Maarten, The Netherlands

An aerial view of Anse Mitan in Martinique, a beautiful Caribbean village with a bustling beach, sailboats moored in the bay, and lush green hills in the distance.
FREE All-Inclusive Upgrade + FREE Hotel Stay + up to $2,000 Onboard Credit*+ 1 more offer
Windstar

21-night Star Collector: A Lesser Antilles Odyssey Cruise

Aboard

Wind Surf

From

Philipsburg, St. Maarten, The Netherlands

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 $2,000 Onboard Credit*+ 1 more offer
Windstar

55-night Star Collector: A Grand Caribbean Adventure Cruise

Aboard

Wind Surf

From

Philipsburg, St. Maarten, The Netherlands

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 $2,000 Onboard Credit*+ 1 more offer
Windstar

14-night Star Collector: Antilles Adventures Cruise

Aboard

Wind Surf

From

Philipsburg, St. Maarten, The Netherlands

Published prices from

$9,559

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.
FREE All-Inclusive Upgrade + FREE Hotel Stay + up to $2,000 Onboard Credit*+ 1 more offer
Windstar

10-night Blue Waters Of The Leeward Islands Cruise

Aboard

Wind Spirit

From

Philipsburg, St. Maarten, The Netherlands

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 $2,000 Onboard Credit*+ 1 more offer
Windstar

17-night Star Collector: Hidden Gems of the Caribbean Cruise

Aboard

Wind Spirit

From

Philipsburg, St. Maarten, The Netherlands

Rocky beach and palm trees in Barbados.
FREE All-Inclusive Upgrade + FREE Hotel Stay + up to $2,000 Onboard Credit*+ 1 more offer
Windstar

7-night Jewels of the Windward Islands Cruise

Aboard

Wind Surf

From

Bridgetown, Barbados

Published prices from

$5,122

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.
FREE All-Inclusive Upgrade + FREE Hotel Stay + up to $2,000 Onboard Credit*+ 1 more offer
Windstar

14-night Star Collector: Captivating Caribbean Cruise

Aboard

Wind Surf

From

Bridgetown, Barbados

Published prices from

$9,947

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 $2,000 Onboard Credit*+ 1 more offer
Windstar

14-night Star Collector: Lovely Leewards Cruise

Aboard

Star Seeker

From

San Juan, Puerto Rico

Published prices from

$11,296

per person*

taxes & fees included

Historic El Morro fortress overlooking the ocean in San Juan, Puerto Rico.
FREE All-Inclusive Upgrade + FREE Hotel Stay + up to $2,000 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 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 $2,000 Onboard Credit*+ 1 more offer
Windstar

28-night Star Collector: Grand Caribbean & Panamanian Adventure Cruise

Aboard

Wind Spirit

From

Philipsburg, St. Maarten, The Netherlands

Rocky beach and palm trees in Barbados.
FREE All-Inclusive Upgrade + FREE Hotel Stay + up to $2,000 Onboard Credit*+ 1 more offer
Windstar

14-night Star Collector: Captivating Caribbean Cruise

Aboard

Wind Spirit

From

Bridgetown, Barbados

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 $2,000 Onboard Credit*+ 1 more offer
Windstar

7-night Windward Island Delights Cruise

Aboard

Wind Spirit

From

Bridgetown, Barbados

Blue Mosque and historic Istanbul skyline with Bosphorus Strait.
FREE All-Inclusive Upgrade + FREE Hotel Stay + up to $2,000 Onboard Credit*+ 1 more offer
Windstar

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

Aboard

Star Legend

From

Istanbul, Turkey

Published prices from

$29,643

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 $2,000 Onboard Credit*+ 1 more offer
Windstar

14-night Star Collector: Lovely Leewards Cruise

Aboard

Star Pride

From

San Juan, Puerto Rico

Published prices from

$4,993

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 $2,000 Onboard Credit*+ 1 more offer
Windstar

7-night Windward Islands Surf & Sunsets Cruise

Aboard

Star Pride

From

San Juan, Puerto Rico

Published prices from

$3,130

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 $2,000 Onboard Credit*+ 1 more offer
Windstar

25-night Star Collector: Southern Caribbean Thanksgiving Jubilee Cruise

Aboard

Wind Star

From

Lisbon, Portugal

Published prices from

$8,656

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 $2,000 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

$9,300

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 $2,000 Onboard Credit*+ 1 more offer
Windstar

11-night Colombian & Southern Caribbean Coastlines Cruise

Aboard

Wind Star

From

Bridgetown, Barbados

Published prices from

$5,330

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 $2,000 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 $2,000 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 $2,000 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

$5,561

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 $2,000 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

*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.