7-night San Juan & The Virgin Islands Cruise From San Juan, Puerto Rico

Windstar

Historic El Morro fortress overlooking the ocean in San Juan, Puerto Rico.
Windstar's Star Pride cruise ship sailing at sunset.
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Sailing Nov 15, 2026 - Mar 20, 2028

Your 7-night Caribbean Cruise at a Glance

Sailings aboard Star Pride depart from San Juan, Puerto Rico with 6 stops in ports-of-call including Jost Van Dyke, St. Maarten (Philipsburg), and Virgin Gorda. The Cruise Web can help you find the best deals and stateroom prices on any of the 8 upcoming sailings in 2026, 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 Cruz Bay, St. John on day 2 and St. Maarten (Philipsburg) on day 5. We can help you with excursions and making the most of any itinerary.

Cruise Ship

Star Pride

Star Pride, built in 1988 and refurbished in 2021, carries 312 passengers with a crew of 190.

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 Pride or 7 of Windstar’s other ships.