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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

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

Blue Mosque and historic Istanbul skyline with Bosphorus Strait.

FREE Champagne, Entertainment, Dining & More*

Windstar

70-night Star Collector: Grand Mediterranean And Latin America Adventure Cruise

Kusadasi (Ephesus)

Aboard

Star Legend

From

Istanbul, Turkey

1 Sailing

Oct 19, 2026

1 Sailing

Oct 19, 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

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

A panoramic view of Gustavia, Saint Barthélemy, featuring a bay filled with luxury yachts and sailboats, framed by lush, green hillsides dotted with houses.

FREE All-Inclusive Package Upgrade*+ 1 more offer

Windstar

28-night Star Collector: Grand Caribbean & Panamanian Adventure Cruise

St. Maarten (Philipsburg)

Aboard

Wind Spirit

From

Philipsburg, St. Maarten, The Netherlands

1 Sailing

Feb 21, 2026

1 Sailing

Feb 21, 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 view of the bustling city of Balboa, Panama, with a scenic coastal road alongside a marina and tall modern skyscrapers in the background.

FREE Champagne, Entertainment, Dining & More*

Windstar

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

San Blas Islands

Cartagena (Colombia)

Aboard

Star Legend

From

Balboa, Panama

1 Sailing

Feb 16, 2027

1 Sailing

Feb 16, 2027

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

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