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

Windstar

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.
Windstar's WInd Surf sailing yacht at sea.
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ABOARD

Wind Surf

4.7

18 reviews

Windstar's WInd Surf sailing yacht at sea.

Departing

Visiting

Philipsburg, St. Maarten, The Netherlands

3 Ports of Call

Sailing Mar 27, 2027 - Mar 19, 2028

from $2,580 per person* taxes and fees included

Your 15-night Caribbean Cruise at a Glance

Sailings aboard Wind Surf depart from Philipsburg, St. Maarten, The Netherlands with 3 stops in ports-of-call including Lisbon, Funchal (Madeira), Portugal, and Porto Santo. The Cruise Web can help you find the best deals and stateroom prices on any of the 2 upcoming sailings in 2027 and 2028.

Departure Port

Philipsburg, St. Maarten, The Netherlands

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 Funchal (Madeira), Portugal on day 12 and Porto Santo on day 13. 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.