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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.

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

14 Sailings

Dec 19, 2026 - Jan 23, 2028

14 Sailings

Dec 19, 2026 - Jan 23, 2028

Published prices from

$4,208

per person*

taxes & fees included

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.

Windstar

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

St. Maarten (Philipsburg)

Aboard

Wind Surf

From

Philipsburg, St. Maarten, The Netherlands

8 Sailings

Dec 26, 2026 - Nov 28, 2027

8 Sailings

Dec 26, 2026 - Nov 28, 2027

Published prices from

$2,432

per person*

taxes & fees included

*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.