Windstar Cruises to Southern Caribbean

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

Overview

A Windstar cruise to the Southern Caribbean offers an elegant and intimate journey through a string of lesser-traveled islands, providing a secluded escape from the larger cruise crowds. Onboard, guests enjoy the luxury of a private yacht with a casual, relaxed atmosphere. The ship's smaller size allows it to access hidden coves and charming harbors that are off-limits to mega-ships, ensuring a more authentic and immersive island experience.

The itineraries are carefully designed to showcase the diverse beauty of the region, from the lush volcanic landscapes of St. Lucia and Dominica to the chic, French-influenced shores of St. Barts. Windstar's voyages focus on "destination immersion," with late-night and overnight stays in ports, giving guests ample time to explore, dine, and experience the local culture after the sun goes down.

Upcoming Windstar Cruises to Southern Caribbean

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A picturesque view of a red and white lighthouse on a rocky cliff overlooking the vast Atlantic Ocean in St. Anthony, Newfoundland and Labrador.

25-night Star Collector Cruise: Autumn In Newfoundland And New England From Boston, Massachusetts

Boston

Rockland

Portland

Halifax (Nova Scotia)

Sydney (Nova Scotia)

+13 more

Aboard

Star Pride

From

Boston, Massachusetts

1 Sailing

Sep 14, 2026

1 Sailing

Sep 14, 2026

Published prices from

$11,498

per person*

taxes & fees included

A low-angle shot of a massive, imposing cliff face rising dramatically from the dark water, with patches of moss and greenery clinging to its textured, gray rock surface.

25-night Star Collector Cruise: Autumn In Newfoundland And New England From Montreal, Quebec

Montreal

Quebec City

Baie-Comeau (Comeau Bay)

Cap-aux-Meules

St. Pierre and Miquelon

+13 more

Aboard

Star Pride

From

Montreal, Quebec

1 Sailing

Sep 25, 2026

1 Sailing

Sep 25, 2026

Published prices from

$11,190

per person*

taxes & fees included

A stunning autumn landscape in Havre-Saint-Pierre, Quebec, with a lake reflecting a forest of trees in various shades of green, yellow, and orange, with a wooden pier in the foreground.

14-night Quebec And Newfoundland Adventure Cruise From Montreal, Quebec

Montreal

Quebec City

Baie-Comeau (Comeau Bay)

Cap-aux-Meules

St. Pierre and Miquelon

+7 more

Aboard

Star Pride

From

Montreal, Quebec

2 Sailings

Sep 25, 2026 - Sep 27, 2027

2 Sailings

Sep 25, 2026 - Sep 27, 2027

Published prices from

$8,680

per person*

taxes & fees included

The iconic Library of Celsus in the ancient city of Ephesus, Turkey, with its magnificent, two-story facade and marble columns standing against a backdrop of cypress trees and green hills.

70-night Star Collector: Grand Mediterranean And Latin America Adventure Cruise From Istanbul, Turkey

Aboard

Star Legend

From

Istanbul, Turkey

1 Sailing

Oct 19, 2026

1 Sailing

Oct 19, 2026

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.

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

24-night Star Collector: Classic Crossing To Spain & More Cruise From Barcelona, Spain

Barcelona

Barcelona (Tarragona)

Aboard

Wind Star

From

Barcelona, Spain

1 Sailing

Oct 31, 2026

1 Sailing

Oct 31, 2026

A scenic view of the white sand beach and lush palm trees of Mystery Island, Aneityum, with calm, turquoise water under a clear blue sky.

23-night Star Collector Cruise: Spanish Mystery & Atlantic Crossing From Barcelona, Spain

Barcelona

Mystery Island (Aneityum)

Aboard

Star Legend

From

Barcelona, Spain

1 Sailing

Nov 4, 2026

1 Sailing

Nov 4, 2026

Published prices from

$6,535

per person*

taxes & fees included

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

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.

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

$4,070

per person*

taxes & fees included

14-night Ocean Crossings Cruise From Lisbon, Portugal

Lisbon

Bridgetown (Barbados)

Aboard

Wind Star

From

Lisbon, Portugal

1 Sailing

Nov 10, 2026

1 Sailing

Nov 10, 2026

Published prices from

$5,206

per person*

taxes & fees included

25-night Star Collector: Southern Caribbean Thanksgiving Jubilee Cruise From Lisbon, Portugal

Lisbon

Bridgetown (Barbados)

Aboard

Wind Star

From

Lisbon, Portugal

1 Sailing

Nov 10, 2026

1 Sailing

Nov 10, 2026

22-night Star Collector Cruise: Caribbean Beats & Transatlantic Treats From Malaga, Spain

Bridgetown (Barbados)

+8 more

Aboard

Star Legend

From

Malaga, Spain

1 Sailing

Nov 12, 2026

1 Sailing

Nov 12, 2026

Published prices from

$5,491

per person*

taxes & fees included

A picturesque view of the historic Cape Spartel Lighthouse on a cliff overlooking the Atlantic Ocean near Tangier, Morocco.

13-night Ocean Crossings Cruise From Malaga, Spain

Bridgetown (Barbados)

Aboard

Star Legend

From

Malaga, Spain

1 Sailing

Nov 12, 2026

1 Sailing

Nov 12, 2026

Published prices from

$3,304

per person*

taxes & fees included

18-night Star Collector: Reefs & Rainforests: The Caribbean, Colombia, Panama & Costa Rica Via The Panama Canal Cruise From Bridgetown, Barbados

Bridgetown (Barbados)

Aboard

Wind Star

From

Bridgetown, Barbados

1 Sailing

Nov 24, 2026

1 Sailing

Nov 24, 2026

Colorful colonial balconies in Cartagena.

11-night Colombian & Southern Caribbean Coastlines Cruise From Bridgetown, Barbados

Bridgetown (Barbados)

Aboard

Wind Star

From

Bridgetown, Barbados

1 Sailing

Nov 24, 2026

1 Sailing

Nov 24, 2026

Published prices from

$7,951

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.

15-night Star Collector: Captivating Caribbean Cruise From Bridgetown, Barbados

Bridgetown (Barbados)

Aboard

Star Legend

From

Bridgetown, Barbados

1 Sailing

Nov 27, 2026

1 Sailing

Nov 27, 2026

Published prices from

$4,439

per person*

taxes & fees included

A vibrant panoramic view of Castries, St. Lucia, with colorful buildings nestled along the harbor and lush green hills in the background under a blue sky with white clouds.

7-night Jewels Of The Windward Islands Cruise From Bridgetown, Barbados

Bridgetown (Barbados)

Aboard

Star Legend

From

Bridgetown, Barbados

1 Sailing

Nov 27, 2026

1 Sailing

Nov 27, 2026

Published prices from

$2,419

per person*

taxes & fees included

A breathtaking aerial view of the iconic Pitons, two majestic volcanic peaks, rising from the turquoise waters of the Caribbean Sea on the island of St. Lucia, with a small bay and sailboats.

16-night Star Collector: Windward Islands & Spanish New World Cruise From Bridgetown, Barbados

Bridgetown (Barbados)

Aboard

Star Legend

From

Bridgetown, Barbados

1 Sailing

Dec 4, 2026

1 Sailing

Dec 4, 2026

Published prices from

$4,414

per person*

taxes & fees included

A breathtaking tropical beach on Mayreau Island, Grenadines, with white sand, tall palm trees, and turquoise water under a perfectly blue sky.

8-night Windward Ways & Tobago Cays Cruise From Bridgetown, Barbados

Bridgetown (Barbados)

Aboard

Star Legend

From

Bridgetown, Barbados

1 Sailing

Dec 4, 2026

1 Sailing

Dec 4, 2026

Published prices from

$2,900

per person*

taxes & fees included

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.

8-night Panama Canal, Cartagena, San Blas Islands & More Cruise From Oranjestad, Aruba, Caribbean

Aboard

Star Legend

From

Oranjestad, Aruba, Caribbean

1 Sailing

Dec 12, 2026

1 Sailing

Dec 12, 2026

Published prices from

$3,686

per person*

taxes & fees included

Lush rainforest and beach in Costa Rica.

16-night Star Collector: Latin America Explorer Cruise From Oranjestad, Aruba, Caribbean

Aboard

Star Legend

From

Oranjestad, Aruba, Caribbean

1 Sailing

Dec 12, 2026

1 Sailing

Dec 12, 2026

Published prices from

$5,719

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.

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

$4,208

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.

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 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.

13-night Latin America Explorer Cruise From Puerto Caldera, Costa Rica

Puerto Caldera (Puntarenas)

Playa Flamingo

Punta Leona

Quepos

Golfo Dulce (Puerto Jimenez)

+8 more

Aboard

Star Legend

From

Puerto Caldera, Costa Rica

1 Sailing

Feb 9, 2027

1 Sailing

Feb 9, 2027

Published prices from

$5,800

per person*

taxes & fees included

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

Fuerte Amador (Panama City)

Aboard

Star Legend

From

Fuerte Amador, Panama

1 Sailing

Feb 16, 2027

1 Sailing

Feb 16, 2027

Published prices from

$3,456

per person*

taxes & fees included

14-night Star Collector: Windward Islands & Spanish New World Cruise From Fuerte Amador, Panama

Fuerte Amador (Panama City)

Aboard

Star Legend

From

Fuerte Amador, Panama

1 Sailing

Feb 16, 2027

1 Sailing

Feb 16, 2027

Published prices from

$8,290

per person*

taxes & fees included

A stunning panoramic view of Rodney Bay on the island of St. Lucia, showing a bustling harbor filled with sailboats, a colorful town, and lush green hills under a bright blue, cloudy sky.

8-night Windward Ways & Tobago Cays Cruise From Oranjestad, Aruba, Caribbean

Aboard

Star Legend

From

Oranjestad, Aruba, Caribbean

1 Sailing

Feb 22, 2027

1 Sailing

Feb 22, 2027

Published prices from

$6,620

per person*

taxes & fees included

A beautiful Porto Santo beach landscape with a long stretch of golden sand, a wicker bench, a wooden fence, and the distinctive mountains of Madeira in the background.

15-night Ocean Crossings Cruise From Bridgetown, Barbados

Bridgetown (Barbados)

Aboard

Star Legend

From

Bridgetown, Barbados

1 Sailing

Mar 2, 2027

1 Sailing

Mar 2, 2027

Published prices from

$2,796

per person*

taxes & fees included

A scenic view of the iconic Plaza de España in Seville, Spain, featuring its grand arcade of arches and columns, a main building with a clock tower, and a bright blue sky.

23-night Star Collector Cruise: Spanish Shores Transatlantic Crossing From Bridgetown, Barbados

Bridgetown (Barbados)

Aboard

Star Legend

From

Bridgetown, Barbados

1 Sailing

Mar 2, 2027

1 Sailing

Mar 2, 2027

Published prices from

$5,567

per person*

taxes & fees included

25-night Star Collector: Autumn In Newfoundland And New England Cruise From Boston, Massachusetts

Boston

Portland

Bar Harbor

Halifax (Nova Scotia)

Charlottetown

+13 more

Aboard

Star Pride

From

Boston, Massachusetts

1 Sailing

Sep 16, 2027

1 Sailing

Sep 16, 2027

Published prices from

$14,478

per person*

taxes & fees included

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

$7,397

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.

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

$4,939

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.

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

$4,350

per person*

taxes & fees included

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.

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

$6,927

per person*

taxes & fees included

14-night Star Collector Cruise: Latin America Explorer From Puerto Caldera, Costa Rica

Puerto Caldera (Puntarenas)

Playa Flamingo

Punta Leona

Quepos

Golfo Dulce (Puerto Jimenez)

+8 more

Aboard

Star Pride

From

Puerto Caldera, Costa Rica

1 Sailing

Feb 21, 2028

1 Sailing

Feb 21, 2028

Published prices from

$5,166

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.

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.

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

$5,073

per person*

taxes & fees included

A cruise ship navigating through the Gatun Locks of the Panama Canal, an important navigational route and popular tourist destination.

7-night Panama Canal, Cartagena, San Blas Islands & More Cruise From Balboa, Panama

Aboard

Star Pride

From

Balboa, Panama

1 Sailing

Feb 28, 2028

1 Sailing

Feb 28, 2028

Published prices from

$2,676

per person*

taxes & fees included

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

$7,097

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.

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

$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.

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

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

$4,655

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.