21-night Star Collector Cruise: Windward Islands, Spanish Cities & Costa Rica 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 Nov 22, 2027

from $6,417 per person* taxes and fees included

Your 21-night Caribbean Cruise at a Glance

Sailings aboard Star Pride depart from San Juan, Puerto Rico with 16 stops in ports-of-call including St. George's, Grenada, Isla Parida, and Bequia, Grenadines. The Cruise Web can help you find the best deals and stateroom prices on the next sailing November 22, 2027.

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 Santo Domingo on day 10 and Panama Canal on day 16. 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.