14-Night CARIBBEAN CRUISE
This 14-night Caribbean (Eastern) cruise aboard the Wind Surf by Windstar Cruises departs St. Maarten (Philipsburg) on January 30, 2027, calling at Anguilla, Tortola Island BVI, Jost Van Dyke, and 9 more ports, and returns February 13, 2027. Cabin prices start from $7,330 per person.
St. Maarten cruise port is one of the busiest in the Caribbean, with ships docking at the A.C.
Read more →Falmouth's historic port was purpose-built for mega-ships and sits in a town known for its well-preserved Georgian colonial architecture. Popular excursions include Dunn's River Falls, bamboo rafting on the Martha Brae River, and Montego Bay beaches.
Read more →St. Maarten cruise port is one of the busiest in the Caribbean, with ships docking at the A.C.
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 →Ocean View 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.