Star Pride: 14-Night Caribbean
This 14-night Caribbean (Eastern) cruise aboard the Star Pride by Windstar Cruises departs San Juan on November 8, 2026, calling at St Georges, Bequia, Mayreau, and 9 more ports, and returns November 22, 2026.
San Juan cruise port is one of the busiest in the Caribbean and one of the few that doubles as both a major embarkation point and a popular port of call. The port sits in Old San Juan, the historic colonial core of Puerto Rico's capital, founded by Spanish colonists in 1521.
Read more →San Juan cruise port is one of the busiest in the Caribbean and one of the few that doubles as both a major embarkation point and a popular port of call. The port sits in Old San Juan, the historic colonial core of Puerto Rico's capital, founded by Spanish colonists in 1521.
Read more →Basseterre cruise port in St. Kitts uses the Port Zante terminal, a purpose-built cruise facility in the heart of Basseterre, the capital of St. Kitts and Nevis. Port Zante includes two dedicated cruise piers capable of berthing the largest modern ships plus a marina, restaurants, shops, and the Amina Craft Market.
Read more →St. Maarten cruise port is one of the busiest in the Caribbean, with ships docking at the A.C.
Read more →Balcony cabin
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Other Caribbean (Eastern) departures
Questions about this sailing
Which ports does it visit?
It sails round trip from San Juan and calls at St Georges, Bequia, Mayreau, Les Saintes, Marigot, San Juan, St. John, St. Kitts, St. Barthelemy, St. Maarten (Philipsburg), Jost Van Dyke and Virgin Gorda, with 1 day at sea.