Windstar

Southern Caribbean Cruises on Windstar

Colorful buildings along the waterfront of Oranjestad, Aruba, a vibrant port of call for a Windstar cruise in the Southern Caribbean.

Upcoming Southern Caribbean Cruises on Windstar

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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

Published prices from

$5,020

per person*

taxes & fees included

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

Published prices from

$5,315

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 Champagne, Entertainment, Dining & More*
Windstar

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

Aboard

Wind Surf

From

Philipsburg, St. Maarten, The Netherlands

Published prices from

$7,136

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 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 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 Champagne, Entertainment, Dining & More*
Windstar

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

Aboard

Star Pride

From

Oranjestad, Aruba, Caribbean

Published prices from

$4,015

per person*

taxes & fees included

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

7-night Jewels of the Windward Islands Cruise

Aboard

Wind Surf

From

Bridgetown, Barbados

Published prices from

$4,222

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 Champagne, Entertainment, Dining & More*
Windstar

14-night Star Collector: Captivating Caribbean Cruise

Aboard

Wind Surf

From

Bridgetown, Barbados

Published prices from

$8,247

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 Champagne, Entertainment, Dining & More*
Windstar

14-night Star Collector: Lovely Leewards Cruise

Aboard

Star Seeker

From

San Juan, Puerto Rico

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

7-night Windward Ways & Tobago Cays Cruise

Aboard

Wind Surf

From

Bridgetown, Barbados

Published prices from

$4,424

per person*

taxes & fees included

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

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

Aboard

Wind Surf

From

Bridgetown, Barbados

Published prices from

$7,766

per person*

taxes & fees included

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

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 Champagne, Entertainment, Dining & More*
Windstar

14-night Star Collector: Caribbean Explorations Cruise

Aboard

Wind Spirit

From

Philipsburg, St. Maarten, The Netherlands

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

8-night In the Wake of the Spanish Armadas Cruise

Aboard

Wind Surf

From

Oranjestad, Aruba, Caribbean

Published prices from

$6,741

per person*

taxes & fees included

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

16-night Star Collector: Natural History Meets Ancient Mystery: Latin America & Beyond Cruise

Aboard

Wind Surf

From

Oranjestad, Aruba, Caribbean

Published prices from

$7,086

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 Champagne, Entertainment, Dining & More*
Windstar

7-night Classic Caribbean Cruise

Aboard

Wind Spirit

From

Philipsburg, St. Maarten, The Netherlands

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

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

Aboard

Wind Spirit

From

Philipsburg, St. Maarten, The Netherlands

Published prices from

$4,360

per person*

taxes & fees included

A scenic shot of the stunning Seven Mile Beach in Grand Cayman, with a wide, sandy beach, calm turquoise water, and resorts with palm trees under a beautiful blue sky.
FREE Champagne, Entertainment, Dining & More*
Windstar

18-night Star Collector: Deep Dive Into the Blue: Underwater Worlds of the Caribbean Cruise

Aboard

Wind Surf

From

Cozumel, Mexico

Published prices from

$8,965

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

Holland America Line

Cunard

Oceania Cruises

Celebrity Cruises

Azamara

Destinations

Douro River

Mexico

Rhône River

Po River

Arctic Circle

Ports

Caudebec-en-Caux, France

Salalah, Oman

Deshaies, Guadeloupe

Cala di Fico, France

Hunter River, Australia

Cruise Ships

S.S. Maria Theresa

Spectrum of the Seas

S.S. Audrey

Star Explorer

Viking Gyda