11-night Gems Of The Leeward Islands Cruise From San Juan, Puerto Rico

Windstar

An aerial view of the colorful waterfront of St. George's, Grenada, with the town's buildings nestled on a hillside and a long, rocky breakwater extending into the calm, turquoise water.
Windstar's Star Pride cruise ship sailing at sunset.
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Sailing Oct 28, 2026

Your 11-night Caribbean Cruise at a Glance

Sailings aboard Star Pride depart from San Juan, Puerto Rico with 9 stops in ports-of-call including Virgin Gorda, Pigeon Island, St. Lucia, and Falmouth Harbour, Antigua. The Cruise Web can help you find the best deals and stateroom prices on the next sailing October 28, 2026.

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 Basseterre, St. Kitts on day 4 and Falmouth Harbour, Antigua 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.