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

95 Results

Sort

A snorkeler swims in the turquoise waters of the Baths National Park on Virgin Gorda, surrounded by massive granite boulders and palm trees.
FREE Champagne, Entertainment, Dining & More*
Windstar

7-night San Juan & The Virgin Islands Cruise

Aboard

Star Pride

From

San Juan, Puerto Rico

Immaculate Conception Cathedral in Colon.
FREE Champagne, Entertainment, Dining & More*
Windstar

20-night Star Collector: Central America & The Caribbean: Cloudforest Coastlines, Canal Locks & Calypso Concerts Cruise

Aboard

Star Pride

From

San Juan, Puerto Rico

Historic El Morro fortress overlooking the ocean in San Juan, Puerto Rico.
FREE Champagne, Entertainment, Dining & More*
Windstar

13-night Star Collector: Beaches & Bastions Of The BVI And Spanish Caribbean Cruise

Aboard

Star Pride

From

San Juan, Puerto Rico

An idyllic white-sand beach with turquoise water and palm trees on Jost Van Dyke, with a lush green hill in the background.
FREE Champagne, Entertainment, Dining & More*
Windstar

12-night Star Collector: Ivory Beaches & Sapphire Seas of the Caribbean Cruise

Aboard

Wind Surf

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.
FREE Champagne, Entertainment, Dining & More*
Windstar

5-night Barefoot Break in the British Virgin Islands Cruise

Aboard

Wind Surf

From

Philipsburg, St. Maarten, The Netherlands

A tranquil beach on Isla Parida, with gentle waves lapping against the sandy shore and a lush green rainforest lining the coast.
FREE Champagne, Entertainment, Dining & More*
Windstar

13-night Star Collector: Coffee, Canal & Callaloo: Central America, Colombia & The Caribbean Cruise

Aboard

Star Pride

From

San Juan, Puerto Rico

Colorful colonial balconies in Cartagena.
FREE Champagne, Entertainment, Dining & More*
Windstar

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

Aboard

Star Pride

From

San Juan, Puerto Rico

Cupecoy Beach with white resort buildings, St. Maarten.
FREE Champagne, Entertainment, Dining & More*
Windstar

7-night Classic Caribbean Cruise

Aboard

Wind Surf

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 Champagne, Entertainment, Dining & More*
Windstar

14-night Star Collector: Caribbean Explorations Cruise

Aboard

Wind Surf

From

Philipsburg, St. Maarten, The Netherlands

Oranjestad, Aruba harbor with boats and colorful Dutch architecture.
FREE Champagne, Entertainment, Dining & More*
Windstar

7-night Enchanting Colombia And Panamanian Islands Cruise

Aboard

Wind Spirit

From

Colon, Panama

An idyllic white-sand beach with turquoise water and palm trees on Jost Van Dyke, with a lush green hill in the background.
FREE Champagne, Entertainment, Dining & More*
Windstar

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

Aboard

Wind Surf

From

Philipsburg, St. Maarten, The Netherlands

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 Champagne, Entertainment, Dining & More*
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 Champagne, Entertainment, Dining & More*
Windstar

8-night An ABC Christmas Cruise

Aboard

Wind Spirit

From

Oranjestad, Aruba, Caribbean

Rocky beach and palm trees in Barbados.
FREE Champagne, Entertainment, Dining & More*
Windstar

7-night Windward Island Delights Cruise

Aboard

Wind Spirit

From

Bridgetown, Barbados

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 Champagne, Entertainment, Dining & More*
Windstar

10-night Sublime Southern Caribbean Cruise

Aboard

Wind Spirit

From

Bridgetown, Barbados

Cupecoy Beach with white resort buildings, St. Maarten.
FREE Champagne, Entertainment, Dining & More*
Windstar

14-night Star Collector: Leeward & Windward Caribbean Havens 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 Champagne, Entertainment, Dining & More*
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 Champagne, Entertainment, Dining & More*
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 Champagne, Entertainment, Dining & More*
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 Champagne, Entertainment, Dining & More*
Windstar

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

Aboard

Star Pride

From

Balboa, Panama

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 Champagne, Entertainment, Dining & More*
Windstar

7-night Lush & Lovely Islands of the Lesser Antilles 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 Champagne, Entertainment, Dining & More*
Windstar

14-night Star Collector: Antilles Adventures Cruise

Aboard

Wind Surf

From

Philipsburg, St. Maarten, The Netherlands

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 Champagne, Entertainment, Dining & More*
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 Champagne, Entertainment, Dining & More*
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*+ 1 more offer
TCW EXCLUSIVE
Windstar

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

Aboard

Star Seeker

From

Miami, Florida

*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

Seabourn Cruise Line

Holland America Line

Viking River Cruises

Azamara

Destinations

Expeditions

Main River

China

Seine River

South American River

Ports

Tianjin (Beijing), China

Puget Sound, Washington

Qikiqtarjuaq, Nunavut, Canada

Riga, Latvia

Ravenna, Italy

Cruise Ships

Viking Vili

Viking Kara

Viking Haki

Viking Gyda

Viking Modi