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

Windstar

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's WInd Surf sailing yacht at sea.
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Sailing Dec 26, 2026 - Mar 5, 2028

Your 7-night Caribbean Cruise at a Glance

Sailings aboard Wind Surf depart from Philipsburg, St. Maarten, The Netherlands with 6 stops in ports-of-call including Charlestown, Roseau, Dominica, and Gustavia. The Cruise Web can help you find the best deals and stateroom prices on any of the 15 upcoming sailings in 2026, 2027 and 2028.

Philipsburg is the vibrant capital of Dutch St. Maarten, where colorful streets, turquoise waters, and duty-free shopping welcome visitors with Caribbean charm. Before you depart Philipsburg, St. Maarten, The Netherlands, we can help you plan travel and accommodations for your Caribbean cruise.

Destination

Caribbean

Stops on your Caribbean voyage will include Mayreau, Grenadines on day 5 and Basseterre, St. Kitts on day 7. We can help you with excursions and making the most of any itinerary.

Cruise Ship

Wind Surf

Wind Surf, built in 1990 and refurbished in 2024, carries 342 passengers with a crew of 210.

Cruise Line

Windstar Cruises

Get away from the crowd and journey to unique destinations aboard Windstar’s intimate small ships. We can help you maximize deals on Caribbean cruises aboard Wind Surf or 7 of Windstar’s other ships.