Windstar

Cruises Aboard the Wind Surf

Windstar's WInd Surf sailing yacht at sea.

Upcoming Windstar Cruises Aboard the Wind Surf

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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.

St. Peter's Basilica, Rome cityscape at sunset.

Up to $500 FREE Onboard Credit*+ 3 more offers

Windstar

7-night Yachtsman's Harbors of the Rivieras Cruise

Rome (Civitavecchia)

Aboard

Wind Surf

From

Civitavecchia, Rome, Italy

1 Sailing

Nov 3, 2025

1 Sailing

Nov 3, 2025

Plaza Mayor in Madrid, Spain.

FREE All-Inclusive Package Upgrade*+ 1 more offer

Windstar

12-night Spanish Symphony & Madrid Medley Cruise/Land Package

Palma de Mallorca

Cartagena (Spain)

Aboard

Wind Surf

From

Madrid, Spain

2 Sailings

Nov 6, 2025 - Oct 26, 2026

2 Sailings

Nov 6, 2025 - Oct 26, 2026

Belém Tower on Tagus River.

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

Windstar

12-night Portuguese Passages & Spanish Shorelines Cruise/Land Package

Palma de Mallorca

Cartagena (Spain)

Aboard

Wind Surf

From

Barcelona, Spain

1 Sailing

Nov 10, 2025

1 Sailing

Nov 10, 2025

Cupecoy Beach with white resort buildings, St. Maarten.

FREE All-Inclusive Package Upgrade*+ 1 more offer

Windstar

14-night Star Collector: Leeward & Windward Caribbean Havens 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

Cupecoy Beach with white resort buildings, St. Maarten.

FREE All-Inclusive Package Upgrade*+ 1 more offer

Windstar

7-night Classic Caribbean Cruise

St. Maarten (Philipsburg)

Iles des Saintes

Aboard

Wind Surf

From

Philipsburg, St. Maarten, The Netherlands

11 Sailings

Dec 7, 2025 - Mar 20, 2027

11 Sailings

Dec 7, 2025 - Mar 20, 2027

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

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

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

A panoramic sunset shot of the beautiful harbor in Palma de Mallorca, Spain, with a marina full of boats and buildings on the surrounding hills.

Up to $500 FREE Onboard Credit*+ 3 more offers

Windstar

15-night Star Collector – Enchantment of the Western Mediterranean Cruise

Rome (Civitavecchia)

Aboard

Wind Surf

From

Civitavecchia, Rome, Italy

1 Sailing

Nov 3, 2025

1 Sailing

Nov 3, 2025

A captivating half-underwater, half-above-water shot of a person snorkeling in the vibrant turquoise waters of the British Virgin Islands with stunning rock formations and palm trees visible above the waterline.

FREE All-Inclusive Package Upgrade*+ 1 more offer

Windstar

19-night Star Collector: Hearty Ports & Rum Punches - A Trans-Atlantic Crossing Cruise

St. Maarten (Philipsburg)

Aboard

Wind Surf

From

Lisbon, Portugal

1 Sailing

Nov 18, 2025

1 Sailing

Nov 18, 2025

A captivating half-underwater, half-above-water shot of a person snorkeling in the vibrant turquoise waters of the British Virgin Islands with stunning rock formations and palm trees visible above the waterline.

FREE All-Inclusive Package Upgrade*+ 1 more offer

Windstar

5-night Barefoot Break in the British Virgin Islands Cruise

St. Maarten (Philipsburg)

Aboard

Wind Surf

From

Philipsburg, St. Maarten, The Netherlands

1 Sailing

Dec 2, 2025

1 Sailing

Dec 2, 2025

An idyllic white-sand beach with turquoise water and palm trees on Jost Van Dyke, with a lush green hill in the background.

FREE All-Inclusive Package Upgrade*+ 1 more offer

Windstar

12-night Star Collector: Ivory Beaches & Sapphire Seas of the Caribbean Cruise

St. Maarten (Philipsburg)

Aboard

Wind Surf

From

Philipsburg, St. Maarten, The Netherlands

1 Sailing

Dec 2, 2025

1 Sailing

Dec 2, 2025

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 beautiful panoramic view of Roseau, Dominica, with a colorful town nestled between the deep blue Caribbean Sea and a backdrop of lush green, volcanic mountains.

FREE All-Inclusive Package Upgrade*+ 1 more offer

Windstar

7-night Lush & Lovely Islands of the Lesser Antilles Cruise

St. Maarten (Philipsburg)

Aboard

Wind Surf

From

Philipsburg, St. Maarten, The Netherlands

1 Sailing

Jan 11, 2026

1 Sailing

Jan 11, 2026

An aerial panoramic shot of the stunning coast of Palamós, Spain, with a beautiful beach, clear turquoise water, and houses built on the hillside.

Up to $500 FREE Onboard Credit*+ 3 more offers

Windstar

12-night Yachtsman’s Mediterranean Rivieras & Madrid Cruise/Land Package

Rome (Civitavecchia)

Aboard

Wind Surf

From

Civitavecchia, Rome, Italy

1 Sailing

Nov 3, 2025

1 Sailing

Nov 3, 2025

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

14-night Ocean Crossings Cruise

St. Maarten (Philipsburg)

Aboard

Wind Surf

From

Lisbon, Portugal

2 Sailings

Nov 18, 2025 - Dec 5, 2026

2 Sailings

Nov 18, 2025 - Dec 5, 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 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

14-night Star Collector: Caribbean Explorations Cruise

St. Maarten (Philipsburg)

Iles des Saintes

Aboard

Wind Surf

From

Philipsburg, St. Maarten, The Netherlands

19 Sailings

Dec 7, 2025 - Mar 13, 2027

19 Sailings

Dec 7, 2025 - Mar 13, 2027

An idyllic white-sand beach with turquoise water and palm trees on Jost Van Dyke, with a lush green hill in the background.

FREE All-Inclusive Package Upgrade*+ 1 more offer

Windstar

6-night Beach Fun & Sun: A Remote Caribbean Getaway Cruise

St. Maarten (Philipsburg)

Falmouth Harbour

Aboard

Wind Surf

From

Philipsburg, St. Maarten, The Netherlands

4 Sailings

Dec 14, 2025 - Mar 28, 2026

4 Sailings

Dec 14, 2025 - Mar 28, 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 scenic panoramic shot from the top of the Rock of Gibraltar, overlooking the city, marina, and the Mediterranean Sea under a bright blue sky.

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

Windstar

8-night Spanish Symphony Cruise

Palma de Mallorca

Cartagena (Spain)

Aboard

Wind Surf

From

Barcelona, Spain

3 Sailings

Nov 10, 2025 - Oct 30, 2026

3 Sailings

Nov 10, 2025 - Oct 30, 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

Immaculate Conception Cathedral in Colon.

FREE All-Inclusive Package Upgrade*+ 1 more offer

Windstar

16-night Star Collector: Natural History Meets Ancient Mystery: Latin America & Beyond Cruise

Cartagena (Colombia)

Aboard

Wind Surf

From

Oranjestad, Aruba, Caribbean

1 Sailing

Feb 1, 2026

1 Sailing

Feb 1, 2026

Immaculate Conception Cathedral in Colon.

FREE All-Inclusive Package Upgrade*+ 1 more offer

Windstar

8-night In the Wake of the Spanish Armadas Cruise

Cartagena (Colombia)

Aboard

Wind Surf

From

Oranjestad, Aruba, Caribbean

1 Sailing

Feb 1, 2026

1 Sailing

Feb 1, 2026