Star Pride: 17-Night Caribbean
This 17-night Caribbean (Eastern) cruise aboard the Star Pride by Windstar Cruises sails from Boston to San Juan, departing October 22, 2027, calling at Hamilton, St George, Gustavia St Barths, and 6 more ports, and returns November 8, 2027. Cabin prices start from $5,700 per person.
Boston is a compact, walkable city with 400 years of American history layered into its streets, parks, and harbor. The Boston cruise port at Flynn Cruiseport (Black Falcon Terminal) sits in South Boston, about 2 miles from downtown and the Freedom Trail.
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 →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 →Starting cabin
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Other Caribbean (Eastern) departures
Questions about this sailing
Which ports does it visit?
It sails from Boston to San Juan and calls at Hamilton, St George, Gustavia St Barths, Virgin Gorda Island BVI, San Juan, St. John, Basseterre St Kitts, St. Maarten (Philipsburg) and Jost Van Dyke, with 4 days at sea.
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