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

Filter

88 Results

Sort

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

Cupecoy Beach with white resort buildings, St. Maarten.
FREE All-Inclusive Upgrade + FREE Hotel Stay + up to $2,000 Onboard Credit*+ 1 more offer
Windstar

7-night Classic Caribbean Cruise

Aboard

Wind Surf

From

Philipsburg, St. Maarten, The Netherlands

Published prices from

$2,651

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 $2,000 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

$4,219

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

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

Aboard

Wind Surf

From

Philipsburg, St. Maarten, The Netherlands

Published prices from

$3,867

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

10-night Sublime Southern Caribbean Cruise

Aboard

Wind Spirit

From

Bridgetown, Barbados

Cupecoy Beach with white resort buildings, St. Maarten.
FREE All-Inclusive Upgrade + FREE Hotel Stay + up to $2,000 Onboard Credit*+ 1 more offer
Windstar

14-night Star Collector: Leeward & Windward Caribbean Havens Cruise

Aboard

Wind Surf

From

Philipsburg, St. Maarten, The Netherlands

Published prices from

$7,647

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

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

Published prices from

$11,570

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

55-night Star Collector: A Grand Caribbean Adventure Cruise

Aboard

Wind Surf

From

Philipsburg, St. Maarten, The Netherlands

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 + FREE Hotel Stay + up to $2,000 Onboard Credit*+ 1 more offer
Windstar

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

Aboard

Star Pride

From

Balboa, Panama

Published prices from

$4,615

per person*

taxes & fees included

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

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

Aboard

Wind Surf

From

Philipsburg, St. Maarten, The Netherlands

Published prices from

$4,236

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 $2,000 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

$8,159

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

Published prices from

$5,333

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 $2,000 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

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

8-night Star Seeker Christening: Dominican Republic and BVI Adventure Cruise

Aboard

Star Seeker

From

Miami, Florida

Published prices from

$7,876

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

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

Aboard

Star Pride

From

Oranjestad, Aruba, Caribbean

Published prices from

$3,715

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

Wind Surf

From

Bridgetown, Barbados

Published prices from

$4,322

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

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

$9,796

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 San Juan & The Virgin Islands Cruise

Aboard

Star Seeker

From

San Juan, Puerto Rico

Published prices from

$5,362

per person*

taxes & fees included

Cupecoy Beach with white resort buildings, St. Maarten.
FREE All-Inclusive Upgrade + FREE Hotel Stay + up to $2,000 Onboard Credit*+ 1 more offer
Windstar

7-night Beach Fun & Sun: A Remote Caribbean Getaway 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 Windward Ways & Tobago Cays Cruise

Aboard

Wind Surf

From

Bridgetown, Barbados

Published prices from

$3,624

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

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

Aboard

Wind Surf

From

Bridgetown, Barbados

Published prices from

$6,766

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

Celebrity Cruises

Avalon Waterways River Cruises

Cunard

Viking Expedition Cruises

Uniworld River Cruises

Destinations

Africa

Western Caribbean

Mekong River

U.S. Pacific Coast

U.S. Rivers & Great Lakes

Ports

Utrecht, The Netherlands

Bardsey Island, Wales

Bazaruto Island, Mozambique

Colombo, Sri Lanka

Dundee, Scotland

Cruise Ships

Viking Tialfi

Enchanted Princess

AmaFiora

Carnival Luminosa

AmaStella