8-night Ocean Crossings Cruise From Lisbon, Portugal

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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Sailing Nov 5, 2027

Your 15-night Caribbean Cruise at a Glance

Sailings aboard Wind Surf depart from Lisbon, Portugal with 3 stops in ports-of-call including Funchal (Madeira), Portugal, Jost Van Dyke, and St. Maarten (Philipsburg). The Cruise Web can help you find the best deals and stateroom prices on the next sailing November 5, 2027.

Departure Port

Lisbon, Portugal

Lisbon is a sun-soaked capital full of old-world charm, vibrant neighborhoods, and sweeping views over the Tagus River. Before you depart Lisbon, Portugal, 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 4 and Jost Van Dyke on day 15. 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.