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*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.

Rocky beach and palm trees in Barbados.

FREE All-Inclusive Package Upgrade*+ 1 more offer

Windstar

7-night Windward Island Delights Cruise

Bridgetown (Barbados)

Iles des Saintes

Aboard

Wind Spirit

From

Bridgetown, Barbados

1 Sailing

Dec 28, 2025

1 Sailing

Dec 28, 2025

Rocky beach and palm trees in Barbados.

FREE All-Inclusive Package Upgrade*+ 1 more offer

Windstar

7-night Jewels of the Windward Islands Cruise

Bridgetown (Barbados)

Aboard

Wind Surf

From

Bridgetown, Barbados

1 Sailing

Jan 18, 2026

1 Sailing

Jan 18, 2026

Rocky beach and palm trees in Barbados.

FREE All-Inclusive Package Upgrade*+ 1 more offer

Windstar

7-night Jewels of the Windward Islands Cruise

Bridgetown (Barbados)

Iles des Saintes

Aboard

Wind Spirit

From

Bridgetown, Barbados

1 Sailing

Mar 21, 2026

1 Sailing

Mar 21, 2026

Rocky beach and palm trees in Barbados.

FREE All-Inclusive Package Upgrade*+ 1 more offer

Windstar

15-night Ocean Crossings Cruise

Bridgetown (Barbados)

Aboard

Wind Spirit

From

Bridgetown, Barbados

1 Sailing

Mar 28, 2026

1 Sailing

Mar 28, 2026

Rocky beach and palm trees in Barbados.

FREE Champagne, Entertainment, Dining & More*

Windstar

7-night Jewels Of The Windward Islands Cruise

Bridgetown (Barbados)

Aboard

Star Legend

From

Bridgetown, Barbados

1 Sailing

Nov 27, 2026

1 Sailing

Nov 27, 2026

Rocky beach and palm trees in Barbados.

FREE All-Inclusive Package Upgrade*+ 1 more offer

Windstar

14-night Star Collector: Captivating Caribbean Cruise

Bridgetown (Barbados)

Iles des Saintes

Aboard

Wind Spirit

From

Bridgetown, Barbados

1 Sailing

Mar 7, 2026

1 Sailing

Mar 7, 2026

Rocky beach and palm trees in Barbados.

FREE All-Inclusive Package Upgrade*+ 1 more offer

Windstar

22-night Star Collector: Caribbean Beats & Transatlantic Treats Cruise

Bridgetown (Barbados)

Iles des Saintes

Aboard

Wind Spirit

From

Bridgetown, Barbados

1 Sailing

Mar 21, 2026

1 Sailing

Mar 21, 2026

Alcazaba fortress in Malaga.

FREE All-Inclusive Package Upgrade*+ 1 more offer

Windstar

25-night Star Collector: Classic Crossing To Spain & More Cruise

Bridgetown (Barbados)

Cartagena (Spain)

Aboard

Wind Spirit

From

Bridgetown, Barbados

1 Sailing

Mar 28, 2026

1 Sailing

Mar 28, 2026

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

FREE All-Inclusive Package Upgrade*+ 1 more offer

Windstar

16-night Ocean Crossings Cruise

Bridgetown (Barbados)

Aboard

Star Pride

From

Bridgetown, Barbados

1 Sailing

Mar 22, 2026

1 Sailing

Mar 22, 2026

Rocky beach and palm trees in Barbados.

FREE All-Inclusive Package Upgrade*+ 1 more offer

Windstar

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

Bridgetown (Barbados)

Aboard

Wind Surf

From

Bridgetown, Barbados

1 Sailing

Jan 25, 2026

1 Sailing

Jan 25, 2026

Rocky beach and palm trees in Barbados.

FREE All-Inclusive Package Upgrade*+ 1 more offer

Windstar

7-night Windward Ways & Tobago Cays Cruise

Bridgetown (Barbados)

Aboard

Wind Surf

From

Bridgetown, Barbados

1 Sailing

Jan 25, 2026

1 Sailing

Jan 25, 2026

Oranjestad, Aruba harbor with boats and colorful Dutch architecture.

FREE All-Inclusive Package Upgrade*+ 1 more offer

Windstar

18-night Star Collector: Reefs & Rainforests: The Caribbean, Colombia, Panama & Costa Rica via the Panama Canal Cruise

Bridgetown (Barbados)

Aboard

Wind Spirit

From

Bridgetown, Barbados

1 Sailing

Nov 18, 2025

1 Sailing

Nov 18, 2025

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 All-Inclusive Package Upgrade*+ 1 more offer

Windstar

14-night Star Collector: Captivating Caribbean Cruise

Bridgetown (Barbados)

Aboard

Wind Surf

From

Bridgetown, Barbados

1 Sailing

Jan 18, 2026

1 Sailing

Jan 18, 2026

A close-up of a small, adorable squirrel monkey with a black cap and a light brown body, perched on a tree branch surrounded by lush, yellow-green leaves.

FREE Champagne, Entertainment, Dining & More*

Windstar

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

Bridgetown (Barbados)

Aboard

Wind Star

From

Bridgetown, Barbados

1 Sailing

Nov 24, 2026

1 Sailing

Nov 24, 2026

A beautiful view from Fort King George in Scarborough, Tobago, with historic cannons overlooking the Caribbean Sea and the town below, framed by lush tropical trees.

FREE Champagne, Entertainment, Dining & More*

Windstar

8-night Windward Ways & Tobago Cays Cruise

Bridgetown (Barbados)

Aboard

Star Legend

From

Bridgetown, Barbados

1 Sailing

Dec 4, 2026

1 Sailing

Dec 4, 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.

FREE All-Inclusive Package Upgrade*+ 1 more offer

Windstar

10-night Sublime Southern Caribbean Cruise

Bridgetown (Barbados)

Aboard

Wind Spirit

From

Bridgetown, Barbados

1 Sailing

Jan 4, 2026

1 Sailing

Jan 4, 2026

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

15-night Star Collector: Captivating Caribbean Cruise

Bridgetown (Barbados)

Aboard

Star Legend

From

Bridgetown, Barbados

1 Sailing

Nov 27, 2026

1 Sailing

Nov 27, 2026

An aerial view of the Kralendijk waterfront in Bonaire, showcasing the contrast between the deep blue ocean and the shallow turquoise water near the shore, with sailboats anchored offshore.

FREE Champagne, Entertainment, Dining & More*

Windstar

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

Bridgetown (Barbados)

Aboard

Star Legend

From

Bridgetown, Barbados

1 Sailing

Dec 4, 2026

1 Sailing

Dec 4, 2026

An aerial view of the colorful waterfront of St. John's, Antigua, with a long pier extending into the calm, blue sea and the town's charming buildings and marina in the background.

FREE All-Inclusive Package Upgrade*+ 1 more offer

Windstar

7-night Jewels of the Windward Islands Cruise

Bridgetown (Barbados)

Iles des Saintes

Aboard

Wind Spirit

From

Bridgetown, Barbados

1 Sailing

Mar 7, 2026

1 Sailing

Mar 7, 2026

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.

FREE All-Inclusive Package Upgrade*+ 1 more offer

Windstar

7-night Windward Island Delights Cruise

Bridgetown (Barbados)

Aboard

Wind Spirit

From

Bridgetown, Barbados

1 Sailing

Mar 15, 2026

1 Sailing

Mar 15, 2026

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

11-night Colombian & Southern Caribbean Coastlines Cruise

Bridgetown (Barbados)

Aboard

Wind Star

From

Bridgetown, Barbados

1 Sailing

Nov 24, 2026

1 Sailing

Nov 24, 2026

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 All-Inclusive Package Upgrade*+ 1 more offer

Windstar

11-night Columbian & Southern Caribbean Coastlines Cruise

Bridgetown (Barbados)

Aboard

Wind Spirit

From

Bridgetown, Barbados

1 Sailing

Nov 18, 2025

1 Sailing

Nov 18, 2025