8-night Windward Ways & Tobago Cays Cruise From Bridgetown, Barbados

Windstar

A breathtaking tropical beach on Mayreau Island, Grenadines, with white sand, tall palm trees, and turquoise water under a perfectly blue sky.
Windstar's Star Legend cruise ship sailing at sunset.
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Sailing Dec 4, 2026

Your 8-night Caribbean Cruise at a Glance

Sailings aboard Star Legend depart from Bridgetown, Barbados with 8 stops in ports-of-call including Willemstad, Curacao, Kralendijk, and Scarborough, Tobago. The Cruise Web can help you find the best deals and stateroom prices on the next sailing December 4, 2026.

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 Scarborough, Tobago on day 3 and Rodney Bay, St. Lucia on day 3. 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.