8 Night Caribbean Cruise
This 8-night Bermuda cruise aboard the Star Pride by Windstar Cruises sails from Boston to San Juan, departing October 20, 2026, calling at Hamilton, St George, and returns October 28, 2026. Cabin prices start from $1,872 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 →Balcony cabin
New to these charts? How to read cruise price history
Other Bermuda 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.