Windstar Cruises to Eastern Caribbean

An underwater view of a sea turtle swimming in the clear blue waters of Barbados in the Eastern Caribbean, a popular excursion on a Silversea cruise.

Overview

A Windstar cruise to the Eastern Caribbean offers a truly intimate and luxurious escape to some of the most stunning islands in the world. Aboard their elegant yachts, guests can enjoy a personalized cruising experience that feels more like sailing on a private vessel. The small ship size is a key advantage, allowing access to exclusive anchorages and smaller ports that larger cruise ships simply cannot reach.

The itineraries are thoughtfully designed to reveal the best of the region, from the chic shores of St. Barts to the lush, volcanic landscapes of Dominica. Windstar's focus on "destination immersion" means more time in port, often with late-night stays, giving guests ample opportunity to explore the vibrant culture, savor local cuisine, and experience the unique charm of each island at a leisurely pace.

Upcoming Windstar Cruises to Eastern Caribbean

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A breathtaking view of the unique, rocky coastline of St. George's, Bermuda, with a tall rock formation rising from the shallow, clear turquoise waters.

Up to $500 FREE Onboard Credit*+ 2 more offers

TCW EXCLUSIVE

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

Aboard

Star Pride

From

Montreal, Quebec

1 Sailing

Oct 9, 2026

1 Sailing

Oct 9, 2026

Published prices from

$6,979

per person*

taxes & fees included

A turquoise and white ferry boat cruises through the harbor in Hamilton, Bermuda, with a backdrop of pastel-colored buildings and houses along the waterfront.

Up to $500 FREE Onboard Credit*+ 2 more offers

TCW EXCLUSIVE

8-night Bermuda Bliss Cruise From Boston, Massachusetts

Aboard

Star Pride

From

Boston, Massachusetts

1 Sailing

Oct 20, 2026

1 Sailing

Oct 20, 2026

Published prices from

$3,427

per person*

taxes & fees included

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.

Up to $500 FREE Onboard Credit*+ 2 more offers

TCW EXCLUSIVE

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

Aboard

Star Pride

From

San Juan, Puerto Rico

1 Sailing

Oct 28, 2026

1 Sailing

Oct 28, 2026

Published prices from

$4,348

per person*

taxes & fees included

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

Up to $500 FREE Onboard Credit*+ 2 more offers

TCW EXCLUSIVE

7-night Windward Islands Surf & Sunsets Cruise From San Juan, Puerto Rico

Aboard

Star Pride

From

San Juan, Puerto Rico

9 Sailings

Nov 8, 2026 - Mar 27, 2028

9 Sailings

Nov 8, 2026 - Mar 27, 2028

Published prices from

$2,411

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.

Up to $500 FREE Onboard Credit*+ 2 more offers

TCW EXCLUSIVE

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

St. Maarten (Philipsburg)

+8 more

Aboard

Star Pride

From

San Juan, Puerto Rico

14 Sailings

Nov 8, 2026 - Mar 20, 2028

14 Sailings

Nov 8, 2026 - Mar 20, 2028

Published prices from

$4,586

per person*

taxes & fees included

Up to $500 FREE Onboard Credit*+ 2 more offers

TCW EXCLUSIVE

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

St. Maarten (Philipsburg)

+2 more

Aboard

Star Pride

From

San Juan, Puerto Rico

8 Sailings

Nov 15, 2026 - Mar 20, 2028

8 Sailings

Nov 15, 2026 - Mar 20, 2028

Published prices from

$2,443

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.

Up to $500 FREE Onboard Credit*+ 2 more offers

TCW EXCLUSIVE

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

Lisbon

St. John's

St. Maarten (Philipsburg)

Falmouth Harbour

Gustavia

+5 more

Aboard

Wind Surf

From

Lisbon, Portugal

1 Sailing

Dec 5, 2026

1 Sailing

Dec 5, 2026

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.

Up to $500 FREE Onboard Credit*+ 2 more offers

TCW EXCLUSIVE

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

St. Maarten (Philipsburg)

Aboard

Wind Surf

From

Philipsburg, St. Maarten, The Netherlands

14 Sailings

Dec 19, 2026 - Jan 23, 2028

14 Sailings

Dec 19, 2026 - Jan 23, 2028

Published prices from

$4,317

per person*

taxes & fees included

Cupecoy Beach with white resort buildings, St. Maarten.

Up to $500 FREE Onboard Credit*+ 2 more offers

TCW EXCLUSIVE

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

St. Maarten (Philipsburg)

Aboard

Wind Surf

From

Philipsburg, St. Maarten, The Netherlands

7 Sailings

Dec 19, 2026 - Mar 13, 2027

7 Sailings

Dec 19, 2026 - Mar 13, 2027

Published prices from

$2,483

per person*

taxes & fees included

A breathtaking panoramic view of Charlotte Amalie harbor in St. Thomas, with a cruise ship anchored in the bay, surrounded by rolling green hills and a colorful sunset.

Up to $500 FREE Onboard Credit*+ 2 more offers

TCW EXCLUSIVE

7-night Classic Caribbean Cruise From Philipsburg, St. Maarten, The Netherlands

St. Maarten (Philipsburg)

Aboard

Wind Surf

From

Philipsburg, St. Maarten, The Netherlands

8 Sailings

Dec 26, 2026 - Nov 28, 2027

8 Sailings

Dec 26, 2026 - Nov 28, 2027

Published prices from

$2,572

per person*

taxes & fees included

A beautiful panoramic shot from a garden in Funchal, Madeira, Portugal, showcasing meticulously manicured flower beds in geometric patterns with the city and the Atlantic Ocean in the background.

Up to $500 FREE Onboard Credit*+ 2 more offers

TCW EXCLUSIVE

15-night Ocean Crossings Cruise From Philipsburg, St. Maarten, The Netherlands

St. Maarten (Philipsburg)

Funchal (Madeira)

Porto Santo

Lisbon

Aboard

Wind Surf

From

Philipsburg, St. Maarten, The Netherlands

1 Sailing

Mar 27, 2027

1 Sailing

Mar 27, 2027

Published prices from

$3,030

per person*

taxes & fees included

Up to $500 FREE Onboard Credit*+ 1 more offer

TCW EXCLUSIVE

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

Halifax (Nova Scotia)

+9 more

Aboard

Star Pride

From

Montreal, Quebec

1 Sailing

Oct 11, 2027

1 Sailing

Oct 11, 2027

Published prices from

$8,859

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.

Up to $500 FREE Onboard Credit*+ 1 more offer

TCW EXCLUSIVE

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

Aboard

Star Pride

From

Boston, Massachusetts

1 Sailing

Oct 22, 2027

1 Sailing

Oct 22, 2027

Published prices from

$5,548

per person*

taxes & fees included

Up to $500 FREE Onboard Credit*+ 1 more offer

TCW EXCLUSIVE

10-night Bermuda Bliss Cruise From Boston, Massachusetts

Aboard

Star Pride

From

Boston, Massachusetts

1 Sailing

Oct 22, 2027

1 Sailing

Oct 22, 2027

Published prices from

$3,027

per person*

taxes & fees included

Up to $500 FREE Onboard Credit*+ 1 more offer

TCW EXCLUSIVE

21-night Star Collector Cruise: Windward Islands, Spanish Cities & Costa Rica From San Juan, Puerto Rico

Aboard

Star Pride

From

San Juan, Puerto Rico

1 Sailing

Nov 22, 2027

1 Sailing

Nov 22, 2027

Published prices from

$7,204

per person*

taxes & fees included

A high-angle view of the bustling harbor of Marigot, St. Martin, with boats and yachts docked along the coast and colorful buildings nestled against the green hills.

Up to $500 FREE Onboard Credit*+ 1 more offer

TCW EXCLUSIVE

14-night Star Collector Cruise: Caribbean Islands & Colombian Coast Discovery From San Juan, Puerto Rico

Aboard

Star Pride

From

San Juan, Puerto Rico

1 Sailing

Nov 22, 2027

1 Sailing

Nov 22, 2027

Published prices from

$4,614

per person*

taxes & fees included

Up to $500 FREE Onboard Credit*+ 1 more offer

TCW EXCLUSIVE

14-night Star Collector: Coffee, Canal & Callaloo: Central America, Colombia & The Caribbean Cruise From San Juan, Puerto Rico

San Juan

Catalina Island/Casa de Campo

Aboard

Star Pride

From

San Juan, Puerto Rico

1 Sailing

Nov 29, 2027

1 Sailing

Nov 29, 2027

Published prices from

$4,941

per person*

taxes & fees included

This is a scenic image of a tropical beach in Santo Domingo, with multiple colorful fishing boats resting on the sandy shore, tall palm trees, and the calm turquoise sea under a bright, clear sky.

Up to $500 FREE Onboard Credit*+ 1 more offer

TCW EXCLUSIVE

7-night The Spanish Main: Rise Of The New World Cruise From San Juan, Puerto Rico

San Juan

Catalina Island/Casa de Campo

Aboard

Star Pride

From

San Juan, Puerto Rico

1 Sailing

Nov 29, 2027

1 Sailing

Nov 29, 2027

Published prices from

$2,416

per person*

taxes & fees included

Up to $500 FREE Onboard Credit*+ 1 more offer

TCW EXCLUSIVE

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

St. Maarten (Philipsburg)

Aboard

Wind Surf

From

Philipsburg, St. Maarten, The Netherlands

1 Sailing

Dec 5, 2027

1 Sailing

Dec 5, 2027

Published prices from

$2,553

per person*

taxes & fees included

Up to $500 FREE Onboard Credit*+ 1 more offer

TCW EXCLUSIVE

14-night Ocean Crossings Cruise From Lisbon, Portugal

Aboard

Star Legend

From

Lisbon, Portugal

1 Sailing

Dec 6, 2027

1 Sailing

Dec 6, 2027

Published prices from

$7,784

per person*

taxes & fees included

Up to $500 FREE Onboard Credit*+ 1 more offer

TCW EXCLUSIVE

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

Aboard

Star Legend

From

Lisbon, Portugal

1 Sailing

Dec 6, 2027

1 Sailing

Dec 6, 2027

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.

Up to $500 FREE Onboard Credit*+ 1 more offer

TCW EXCLUSIVE

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

San Juan

Cruz Bay

Gustavia

St. Maarten (Philipsburg)

Basseterre

+2 more

Aboard

Star Legend

From

San Juan, Puerto Rico

5 Sailings

Dec 20, 2027 - Feb 14, 2028

5 Sailings

Dec 20, 2027 - Feb 14, 2028

Published prices from

$2,443

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.

Up to $500 FREE Onboard Credit*+ 1 more offer

TCW EXCLUSIVE

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

Aboard

Star Legend

From

San Juan, Puerto Rico

9 Sailings

Dec 20, 2027 - Feb 14, 2028

9 Sailings

Dec 20, 2027 - Feb 14, 2028

Published prices from

$4,586

per person*

taxes & fees included

Up to $500 FREE Onboard Credit*+ 1 more offer

TCW EXCLUSIVE

7-night Windward Islands Surf & Sunsets Cruise From San Juan, Puerto Rico

Aboard

Star Legend

From

San Juan, Puerto Rico

5 Sailings

Dec 27, 2027 - Feb 21, 2028

5 Sailings

Dec 27, 2027 - Feb 21, 2028

Published prices from

$2,411

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.

Up to $500 FREE Onboard Credit*+ 1 more offer

TCW EXCLUSIVE

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

Puerto Caldera (Puntarenas)

Playa Flamingo

Punta Leona

Quepos

Golfo Dulce (Puerto Jimenez)

+14 more

Aboard

Star Pride

From

Puerto Caldera, Costa Rica

1 Sailing

Feb 21, 2028

1 Sailing

Feb 21, 2028

Published prices from

$7,586

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.

Up to $500 FREE Onboard Credit*+ 1 more offer

TCW EXCLUSIVE

22-night Star Collector Cruise: Caribbean Charms To Iberian Shores From San Juan, Puerto Rico

Aboard

Star Legend

From

San Juan, Puerto Rico

1 Sailing

Feb 21, 2028

1 Sailing

Feb 21, 2028

Published prices from

$2,451

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.

Up to $500 FREE Onboard Credit*+ 1 more offer

TCW EXCLUSIVE

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

Aboard

Star Pride

From

Balboa, Panama

1 Sailing

Feb 28, 2028

1 Sailing

Feb 28, 2028

Published prices from

$5,045

per person*

taxes & fees included

An aerial view of Agadir, Morocco, showcasing the city's long sandy beach and curving coastline, with a busy marina and port in the foreground.

Up to $500 FREE Onboard Credit*+ 1 more offer

TCW EXCLUSIVE

15-night Ocean Crossings Cruise From San Juan, Puerto Rico

Aboard

Star Legend

From

San Juan, Puerto Rico

1 Sailing

Feb 28, 2028

1 Sailing

Feb 28, 2028

Up to $500 FREE Onboard Credit*+ 1 more offer

TCW EXCLUSIVE

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

Aboard

Star Pride

From

Oranjestad, Aruba, Caribbean

1 Sailing

Mar 6, 2028

1 Sailing

Mar 6, 2028

Published prices from

$7,246

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.

Up to $500 FREE Onboard Credit*+ 1 more offer

TCW EXCLUSIVE

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

Aboard

Star Pride

From

Oranjestad, Aruba, Caribbean

1 Sailing

Mar 6, 2028

1 Sailing

Mar 6, 2028

Published prices from

$4,920

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.

Up to $500 FREE Onboard Credit*+ 1 more offer

TCW EXCLUSIVE

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

Aboard

Star Pride

From

Oranjestad, Aruba, Caribbean

1 Sailing

Mar 6, 2028

1 Sailing

Mar 6, 2028

Published prices from

$2,859

per person*

taxes & fees included

Up to $500 FREE Onboard Credit*+ 1 more offer

TCW EXCLUSIVE

23-night Star Collector Cruise: Tropical Horizons To Historic Amsterdam From San Juan, Puerto Rico

Aboard

Star Pride

From

San Juan, Puerto Rico

1 Sailing

Mar 27, 2028

1 Sailing

Mar 27, 2028

Published prices from

$4,719

per person*

taxes & fees included

Tulip fields with traditional windmills, showcasing the beauty of the Netherlands in springtime.

Up to $500 FREE Onboard Credit*+ 1 more offer

TCW EXCLUSIVE

16-night Ocean Crossings Cruise From San Juan, Puerto Rico

Aboard

Star Pride

From

San Juan, Puerto Rico

1 Sailing

Apr 3, 2028

1 Sailing

Apr 3, 2028

Published prices from

$2,760

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.

Windstar Cruises to Eastern Caribbean

Upcoming Windstar Cruises to Eastern Caribbean

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

$6,979

8-night Bermuda Bliss Cruise From Boston, Massachusetts

$3,427

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

$4,348

7-night Windward Islands Surf & Sunsets Cruise From San Juan, Puerto Rico

$2,411

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

$4,586

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

$2,443

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

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

$4,317

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

$2,483

7-night Classic Caribbean Cruise From Philipsburg, St. Maarten, The Netherlands

$2,572

15-night Ocean Crossings Cruise From Philipsburg, St. Maarten, The Netherlands

$3,030

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

$8,859

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

$5,548

10-night Bermuda Bliss Cruise From Boston, Massachusetts

$3,027

21-night Star Collector Cruise: Windward Islands, Spanish Cities & Costa Rica From San Juan, Puerto Rico

$7,204

14-night Star Collector Cruise: Caribbean Islands & Colombian Coast Discovery From San Juan, Puerto Rico

$4,614

14-night Star Collector: Coffee, Canal & Callaloo: Central America, Colombia & The Caribbean Cruise From San Juan, Puerto Rico

$4,941

7-night The Spanish Main: Rise Of The New World Cruise From San Juan, Puerto Rico

$2,416

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

$2,553

14-night Ocean Crossings Cruise From Lisbon, Portugal

$7,784

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

$11,676

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

$2,443

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

$4,586

7-night Windward Islands Surf & Sunsets Cruise From San Juan, Puerto Rico

$2,411

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

$7,586

22-night Star Collector Cruise: Caribbean Charms To Iberian Shores From San Juan, Puerto Rico

$2,451

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

$5,045

15-night Ocean Crossings Cruise From San Juan, Puerto Rico

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

$7,246

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

$4,920

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

$2,859

23-night Star Collector Cruise: Tropical Horizons To Historic Amsterdam From San Juan, Puerto Rico

$4,719

16-night Ocean Crossings Cruise From San Juan, Puerto Rico

$2,760

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