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

7-night Yachtsman's Harbors of the Rivieras Cruise

Aboard

Wind Surf

From

Civitavecchia, Rome, Italy

1 Sailing

Nov 3, 2025

1 Sailing

Nov 3, 2025

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

Aboard

Wind Surf

From

Barcelona, Spain

1 Sailing

Nov 10, 2025

1 Sailing

Nov 10, 2025

Cupecoy Beach with white resort buildings, St. Maarten.

14-night Star Collector: Leeward & Windward Caribbean Havens Cruise

Aboard

Wind Surf

From

Philipsburg, St. Maarten, The Netherlands

1 Sailing

Jan 4, 2026

1 Sailing

Jan 4, 2026

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

Aboard

Wind Surf

From

Madrid, Spain

2 Sailings

Nov 6, 2025 - Oct 26, 2026

2 Sailings

Nov 6, 2025 - Oct 26, 2026

7-night Jewels of the Windward Islands Cruise

Aboard

Wind Surf

From

Bridgetown, Barbados

1 Sailing

Jan 18, 2026

1 Sailing

Jan 18, 2026

7-night Windward Ways & Tobago Cays Cruise

Aboard

Wind Surf

From

Bridgetown, Barbados

1 Sailing

Jan 25, 2026

1 Sailing

Jan 25, 2026

7-night Classic Caribbean Cruise

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

Immaculate Conception Cathedral in Colon.

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

Aboard

Wind Surf

From

Oranjestad, Aruba, Caribbean

1 Sailing

Feb 1, 2026

1 Sailing

Feb 1, 2026

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

Aboard

Wind Surf

From

Bridgetown, Barbados

1 Sailing

Jan 25, 2026

1 Sailing

Jan 25, 2026

8-night In the Wake of the Spanish Armadas Cruise

Aboard

Wind Surf

From

Oranjestad, Aruba, Caribbean

1 Sailing

Feb 1, 2026

1 Sailing

Feb 1, 2026

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.

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

Lisbon

Aboard

Wind Surf

From

Lisbon, Portugal

1 Sailing

Nov 18, 2025

1 Sailing

Nov 18, 2025

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

14-night Star Collector: Caribbean Explorations Cruise

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 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.

14-night Ocean Crossings Cruise

Lisbon

St. John's

Aboard

Wind Surf

From

Lisbon, Portugal

2 Sailings

Nov 18, 2025 - Dec 5, 2026

2 Sailings

Nov 18, 2025 - Dec 5, 2026

5-night Barefoot Break in the British Virgin Islands Cruise

Aboard

Wind Surf

From

Philipsburg, St. Maarten, The Netherlands

1 Sailing

Dec 2, 2025

1 Sailing

Dec 2, 2025

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.

21-night Star Collector: A Lesser Antilles Odyssey Cruise

Aboard

Wind Surf

From

Philipsburg, St. Maarten, The Netherlands

1 Sailing

Jan 4, 2026

1 Sailing

Jan 4, 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.

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

Aboard

Wind Surf

From

Philipsburg, St. Maarten, The Netherlands

1 Sailing

Jan 11, 2026

1 Sailing

Jan 11, 2026

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

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

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

Aboard

Wind Surf

From

Philipsburg, St. Maarten, The Netherlands

1 Sailing

Dec 2, 2025

1 Sailing

Dec 2, 2025

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

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

Aboard

Wind Surf

From

Civitavecchia, Rome, Italy

1 Sailing

Nov 3, 2025

1 Sailing

Nov 3, 2025

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.

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

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.

14-night Star Collector: Captivating Caribbean Cruise

Aboard

Wind Surf

From

Bridgetown, Barbados

1 Sailing

Jan 18, 2026

1 Sailing

Jan 18, 2026

55-night Star Collector: A Grand Caribbean Adventure Cruise

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

Aboard

Wind Surf

From

Philipsburg, St. Maarten, The Netherlands

1 Sailing

Jan 4, 2026

1 Sailing

Jan 4, 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*+ 3 more offers

8-night Spanish Symphony Cruise

Aboard

Wind Surf

From

Barcelona, Spain

3 Sailings

Nov 10, 2025 - Oct 30, 2026

3 Sailings

Nov 10, 2025 - Oct 30, 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.

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

Aboard

Wind Surf

From

Civitavecchia, Rome, Italy

1 Sailing

Nov 3, 2025

1 Sailing

Nov 3, 2025

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

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

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.

14-night Star Collector: Antilles Adventures Cruise