Windstar

Windstar Cruises from Philipsburg, St. Maarten, The Netherlands

Cupecoy Beach with white resort buildings, St. Maarten.

Upcoming Windstar Cruises from Philipsburg, St. Maarten, The Netherlands

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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.

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

Windstar

14-night Star Collector: Caribbean Explorations Cruise From Philipsburg, St. Maarten, The Netherlands

St. Maarten (Philipsburg)

Falmouth Harbour

Aboard

Wind Surf

From

Philipsburg, St. Maarten, The Netherlands

13 Sailings

Dec 19, 2026 - Mar 13, 2027

13 Sailings

Dec 19, 2026 - Mar 13, 2027

Cupecoy Beach with white resort buildings, St. Maarten.

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

Windstar

7-night Beach Fun & Sun: A Remote Caribbean Getaway Cruise From Philipsburg, St. Maarten, The Netherlands

St. Maarten (Philipsburg)

Falmouth Harbour

Aboard

Wind Surf

From

Philipsburg, St. Maarten, The Netherlands

7 Sailings

Dec 19, 2026 - Mar 13, 2027

7 Sailings

Dec 19, 2026 - Mar 13, 2027

A breathtaking panoramic view of Charlotte Amalie harbor in St. Thomas, with a cruise ship anchored in the bay, surrounded by rolling green hills and a colorful sunset.

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

Windstar

7-night Classic Caribbean Cruise From Philipsburg, St. Maarten, The Netherlands

St. Maarten (Philipsburg)

Aboard

Wind Surf

From

Philipsburg, St. Maarten, The Netherlands

15 Sailings

Dec 26, 2026 - Mar 5, 2028

15 Sailings

Dec 26, 2026 - Mar 5, 2028

A low-angle shot of the magnificent Palacio Consistorial, the town hall of Cartagena, Spain, showcasing its ornate, white marble facade and domed rooftops against a blue sky.

Up to $500 FREE Onboard Credit*+ 1 more offer

Windstar

23-night Star Collector: Atlantic Interludes & Iberian Indulgences Cruise From Philipsburg, St. Maarten, The Netherlands

St. Maarten (Philipsburg)

Funchal (Madeira)

Seville (Cadiz)

Aboard

Wind Surf

From

Philipsburg, St. Maarten, The Netherlands

1 Sailing

Mar 27, 2027

1 Sailing

Mar 27, 2027

A beautiful panoramic shot from a garden in Funchal, Madeira, Portugal, showcasing meticulously manicured flower beds in geometric patterns with the city and the Atlantic Ocean in the background.

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

Windstar

15-night Ocean Crossings Cruise From Philipsburg, St. Maarten, The Netherlands

St. Maarten (Philipsburg)

Funchal (Madeira)

Aboard

Wind Surf

From

Philipsburg, St. Maarten, The Netherlands

2 Sailings

Mar 27, 2027 - Mar 19, 2028

2 Sailings

Mar 27, 2027 - Mar 19, 2028

Cupecoy Beach with white resort buildings, St. Maarten.

Up to $500 FREE Onboard Credit*

Windstar

8-night Beach Fun & Sun Cruise: A Remote Caribbean Getaway From Philipsburg, St. Maarten, The Netherlands

St. Maarten (Philipsburg)

Aboard

Wind Surf

From

Philipsburg, St. Maarten, The Netherlands

2 Sailings

Nov 20 - Dec 19, 2027

2 Sailings

Nov 20 - Dec 19, 2027

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

Up to $500 FREE Onboard Credit*

Windstar

15-night Star Collector Cruise: Caribbean Explorations From Philipsburg, St. Maarten, The Netherlands

St. Maarten (Philipsburg)

Aboard

Wind Surf

From

Philipsburg, St. Maarten, The Netherlands

3 Sailings

Nov 20 - Dec 19, 2027

3 Sailings

Nov 20 - Dec 19, 2027

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

Up to $500 FREE Onboard Credit*

Windstar

14-night Star Collector Cruise: Caribbean Explorations From Philipsburg, St. Maarten, The Netherlands

St. Maarten (Philipsburg)

Iles des Saintes

Aboard

Wind Surf

From

Philipsburg, St. Maarten, The Netherlands

11 Sailings

Nov 28, 2027 - Mar 5, 2028

11 Sailings

Nov 28, 2027 - Mar 5, 2028

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

Up to $500 FREE Onboard Credit*+ 1 more offer

Windstar

7-night Beach Fun & Sun: A Remote Caribbean Getaway From Philipsburg, St. Maarten, The Netherlands

St. Maarten (Philipsburg)

Falmouth Harbour

Aboard

Wind Surf

From

Philipsburg, St. Maarten, The Netherlands

1 Sailing

Dec 5, 2027

1 Sailing

Dec 5, 2027

Cupecoy Beach with white resort buildings, St. Maarten.

Up to $500 FREE Onboard Credit*

Windstar

13-night Star Collector Cruise: Caribbean Explorations From Philipsburg, St. Maarten, The Netherlands

St. Maarten (Philipsburg)

Iles des Saintes

Aboard

Wind Surf

From

Philipsburg, St. Maarten, The Netherlands

2 Sailings

Dec 27, 2027 - Jan 3, 2028

2 Sailings

Dec 27, 2027 - Jan 3, 2028

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

Up to $500 FREE Onboard Credit*

Windstar

6-night Beach Fun & Sun Cruise: A Remote Caribbean Getaway From Philipsburg, St. Maarten, The Netherlands

St. Maarten (Philipsburg)

Aboard

Wind Surf

From

Philipsburg, St. Maarten, The Netherlands

1 Sailing

Jan 3, 2028

1 Sailing

Jan 3, 2028

Cupecoy Beach with white resort buildings, St. Maarten.

Up to $500 FREE Onboard Credit*

Windstar

7-night Beach Fun & Sun Cruise: A Remote Caribbean Getaway From Philipsburg, St. Maarten, The Netherlands

St. Maarten (Philipsburg)

Aboard

Wind Surf

From

Philipsburg, St. Maarten, The Netherlands

5 Sailings

Jan 16 - Mar 12, 2028

5 Sailings

Jan 16 - Mar 12, 2028

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.

Up to $500 FREE Onboard Credit*

Windstar

22-night Star Collector Cruise: Hearty Ports & Rum Punches - A Transatlantic Crossing From Philipsburg, St. Maarten, The Netherlands

St. Maarten (Philipsburg)

Aboard

Wind Surf

From

Philipsburg, St. Maarten, The Netherlands

1 Sailing

Mar 12, 2028

1 Sailing

Mar 12, 2028

*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.