14 Night Caribbean Cruise
This 14-night Caribbean (Eastern) cruise aboard the Star Pride by Windstar Cruises departs San Juan on December 27, 2026, calling at St. John, Gustavia St Barths, Basseterre St Kitts, and 9 more ports, and returns January 10, 2027. Cabin prices start from $5,554 per person.
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 →Balcony cabin
New to these charts? How to read cruise price history
Other Caribbean (Eastern) departures
We may earn a commission when you book through this link, at no extra cost to you.
Track prices
Get emailed when double occupancy drops below your target.
We may earn a commission when you book through this link, at no extra cost to you.