15-night Ocean Crossings Cruise From Bridgetown, Barbados

Windstar

A beautiful Porto Santo beach landscape with a long stretch of golden sand, a wicker bench, a wooden fence, and the distinctive mountains of Madeira in the background.
Windstar's Star Legend cruise ship sailing at sunset.
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Sailing Mar 2, 2027

from $2,946 per person* taxes and fees included

Your 15-night Caribbean Cruise at a Glance

Sailings aboard Star Legend depart from Bridgetown, Barbados with 4 stops in ports-of-call including Lisbon, Porto Santo, and Funchal (Madeira), Portugal. The Cruise Web can help you find the best deals and stateroom prices on the next sailing March 2, 2027.

Departure Port

Bridgetown, Barbados

Barbados, where the weather is impeccable, the beaches are beautiful and the food is fantastic. Before you depart Bridgetown, Barbados, 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 11 and Porto Santo on day 12. We can help you with excursions and making the most of any itinerary.

Cruise Ship

Star Legend

Star Legend, built in 1992 and refurbished in 2021, carries 312 passengers with a crew of 200.

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 Star Legend or 7 of Windstar’s other ships.