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A picturesque view of a small town nestled at the base of a lush, green mountain on Iles des Saintes, Guadeloupe, with boats moored in the deep blue water and fluffy clouds in the sky.

FREE All-Inclusive Upgrade*+ 1 more offer

Windstar

14-night Star Collector: Caribbean Explorations Cruise

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

Published prices from

$5,419

per person*

taxes & fees included

Cupecoy Beach with white resort buildings, St. Maarten.

FREE All-Inclusive Upgrade*+ 1 more offer

Windstar

7-night Classic Caribbean Cruise

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

$2,851

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.