Windstar

Windstar Cruises from Bridgetown, Barbados

Rocky beach and palm trees in Barbados.

Upcoming Windstar Cruises from Bridgetown, Barbados

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Rocky beach and palm trees in Barbados.

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

Windstar

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.

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

Windstar

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.

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

Windstar

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

$4,767

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.

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

Windstar

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.

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

Windstar

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

$6,059

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.

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

Windstar

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

$2,700

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.

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

Windstar

15-night Ocean Crossings Cruise From Bridgetown, Barbados

Bridgetown (Barbados)

Funchal (Madeira)

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.

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

Windstar

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

Bridgetown (Barbados)

Funchal (Madeira)

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

*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.