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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

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

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

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

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

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

14-night Star Collector: Antilles Adventures Cruise

St. Maarten (Philipsburg)

Aboard

Wind Surf

From

Philipsburg, St. Maarten, The Netherlands

1 Sailing

Jan 11, 2026

1 Sailing

Jan 11, 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

15-night Star Collector: Antilles Adventure Cruise

St. Maarten (Philipsburg)

Iles des Saintes

Aboard

Wind Spirit

From

Philipsburg, St. Maarten, The Netherlands

1 Sailing

Feb 28, 2026

1 Sailing

Feb 28, 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 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

28-night Star Collector: The Best Of The Windward & Leeward Isles Cruise

St. Maarten (Philipsburg)

Falmouth Harbour

Aboard

Wind Surf

From

Philipsburg, St. Maarten, The Netherlands

1 Sailing

Jan 4, 2026

1 Sailing

Jan 4, 2026

An aerial view of Anse Mitan in Martinique, a beautiful Caribbean village with a bustling beach, sailboats moored in the bay, and lush green hills in the distance.

FREE All-Inclusive Package Upgrade*+ 1 more offer

Windstar

21-night Star Collector: A Lesser Antilles Odyssey Cruise

St. Maarten (Philipsburg)

Falmouth Harbour

Aboard

Wind Surf

From

Philipsburg, St. Maarten, The Netherlands

1 Sailing

Jan 4, 2026

1 Sailing

Jan 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 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.

FREE All-Inclusive Package Upgrade*+ 1 more offer

Windstar

10-night Blue Waters Of The Leeward Islands Cruise

St. Maarten (Philipsburg)

Aboard

Wind Spirit

From

Philipsburg, St. Maarten, The Netherlands

1 Sailing

Jan 14, 2026

1 Sailing

Jan 14, 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

55-night Star Collector: A Grand Caribbean Adventure Cruise

St. Maarten (Philipsburg)

Falmouth Harbour

Aboard

Wind Surf

From

Philipsburg, St. Maarten, The Netherlands

1 Sailing

Jan 4, 2026

1 Sailing

Jan 4, 2026

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 snorkeler swims in the turquoise waters of the Baths National Park on Virgin Gorda, surrounded by massive granite boulders and palm trees.

FREE All-Inclusive Package Upgrade*+ 1 more offer

Windstar

17-night Star Collector: Hidden Gems of the Caribbean Cruise

St. Maarten (Philipsburg)

Aboard

Wind Spirit

From

Philipsburg, St. Maarten, The Netherlands

1 Sailing

Jan 14, 2026

1 Sailing

Jan 14, 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

22-night Star Collector: A Lesser Antilles Odyssey Cruise

St. Maarten (Philipsburg)

Aboard

Wind Spirit

From

Philipsburg, St. Maarten, The Netherlands

1 Sailing

Feb 21, 2026

1 Sailing

Feb 21, 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