7-night Windward Islands Surf & Sunsets Cruise From San Juan, Puerto Rico

Windstar

A high-angle view of the bustling harbor of Marigot, St. Martin, with boats and yachts docked along the coast and colorful buildings nestled against the green hills.
Windstar's Star Legend cruise ship sailing at sunset.
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Sailing Dec 27, 2027 - Feb 21, 2028

from $2,411 per person* taxes and fees included

Your 7-night Caribbean Cruise at a Glance

Sailings aboard Star Legend depart from San Juan, Puerto Rico with 5 stops in ports-of-call including Iles des Saintes, Mayreau, Grenadines, and Bequia, Grenadines. The Cruise Web can help you find the best deals and stateroom prices on any of the 5 upcoming sailings in 2027 and 2028.

Departure Port

San Juan, Puerto Rico

A lively Caribbean departure hub where historic streets, oceanfront fortresses, and vibrant island culture create the perfect start to your cruise vacation. Before you depart San Juan, Puerto Rico, we can help you plan travel and accommodations for your Caribbean cruise.

Destination

Caribbean

Stops on your Caribbean voyage will include St. George's, Grenada on day 3 and Mayreau, Grenadines on day 5. 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.