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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.
Windstar

11-night Gems Of The Leeward Islands Cruise From San Juan, Puerto Rico

Aboard

Star Pride

From

San Juan, Puerto Rico

Published prices from

$4,568

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.
Windstar

14-night Star Collector: Lovely Leewards Cruise From San Juan, Puerto Rico

Aboard

Star Pride

From

San Juan, Puerto Rico

Published prices from

$4,070

per person*

taxes & fees included

Historic El Morro fortress overlooking the ocean in San Juan, Puerto Rico.
Windstar

7-night San Juan & The Virgin Islands Cruise From San Juan, Puerto Rico

Aboard

Star Pride

From

San Juan, Puerto Rico

Published prices from

$2,548

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.
Windstar

21-night Star Collector: Hearty Ports & Rum Punches - A Transatlantic Crossing Cruise From Lisbon, Portugal

Aboard

Wind Surf

From

Lisbon, Portugal

Cupecoy Beach with white resort buildings, St. Maarten.
Windstar

7-night Beach Fun & Sun: A Remote Caribbean Getaway Cruise From Philipsburg, St. Maarten, The Netherlands

Aboard

Wind Surf

From

Philipsburg, St. Maarten, The Netherlands

Published prices from

$2,623

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.
Windstar

14-night Star Collector: Caribbean Explorations Cruise From Philipsburg, St. Maarten, The Netherlands

Aboard

Wind Surf

From

Philipsburg, St. Maarten, The Netherlands

Published prices from

$4,208

per person*

taxes & fees included

Historic El Morro fortress overlooking the ocean in San Juan, Puerto Rico.
Windstar

21-night Star Collector: Fall Leaves & Caribbean Breezes Cruise From Montreal, Quebec

Aboard

Star Pride

From

Montreal, Quebec

Published prices from

$7,187

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.
Windstar

17-night Star Collector Cruise: Bermuda & Caribbean Island Explorer From Boston, Massachusetts

Aboard

Star Pride

From

Boston, Massachusetts

Published prices from

$4,926

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.
Windstar

10-night Bermuda Bliss Cruise From Boston, Massachusetts

Aboard

Star Pride

From

Boston, Massachusetts

Published prices from

$3,027

per person*

taxes & fees included

Historic El Morro fortress overlooking the ocean in San Juan, Puerto Rico.
Windstar

21-night Star Collector Cruise: Atlantic Crossing To The Virgin Islands From Lisbon, Portugal

Aboard

Star Legend

From

Lisbon, Portugal

Published prices from

$11,676

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.
Windstar

7-night San Juan & The Virgin Islands Cruise From San Juan, Puerto Rico

Aboard

Star Legend

From

San Juan, Puerto Rico

Published prices from

$2,723

per person*

taxes & fees included

A breathtaking panoramic view of Cruz Bay, St. John, showcasing a vibrant coastal town with white-sand beaches, clear turquoise waters, and numerous boats in the harbor.
Windstar

14-night Star Collector Cruise: Lovely Leewards From San Juan, Puerto Rico

Aboard

Star Legend

From

San Juan, Puerto Rico

Published prices from

$4,350

per person*

taxes & fees included

A close-up shot of two cougars, or pumas, resting on a rocky ledge. The cougar in the foreground looks directly at the camera, its tawny-colored face and alert eyes focused, while the other cougar is curled up and resting behind it.
Windstar

21-night Star Collector Cruise: Costa Rica, Panama & Aruba From Puerto Caldera, Costa Rica

Aboard

Star Pride

From

Puerto Caldera, Costa Rica

Published prices from

$6,927

per person*

taxes & fees included

An aerial view of the bustling city of Balboa, Panama, with a scenic coastal road alongside a marina and tall modern skyscrapers in the background.
Windstar

14-night Star Collector Cruise: Panama, Aruba & The British Virgin Islands From Balboa, Panama

Aboard

Star Pride

From

Balboa, Panama

Published prices from

$5,073

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.
Windstar

21-night Star Collector Cruise: Caribbean Collection: ABC, BVI & The Windwards From Oranjestad, Aruba, Caribbean

Aboard

Star Pride

From

Oranjestad, Aruba, Caribbean

Published prices from

$7,097

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.
Windstar

14-night Star Collector Cruise: Windward Islands, ABC Islands & The Virgin Islands From Oranjestad, Aruba, Caribbean

Aboard

Star Pride

From

Oranjestad, Aruba, Caribbean

Published prices from

$5,046

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.
Windstar

7-night Island Trails Cruise: Aruba To The Virgin Islands From Oranjestad, Aruba, Caribbean

Aboard

Star Pride

From

Oranjestad, Aruba, Caribbean

Published prices from

$3,559

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.