Star Pride: 21-Night Canada
This 21-night Eastern Canada & New England cruise aboard the Star Pride by Windstar Cruises sails from Montreal to San Juan, departing October 11, 2027, calling at Quebec City, Gaspe, Sydney, and 8 more ports, and returns November 1, 2027. Cabin prices start from $9,993 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
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Other Eastern Canada & New England departures
Questions about this sailing
How much does this cruise cost per night?
Ocean view cabins start at $9,993 per person for the 21 nights, about $476 a night, with taxes and port fees included. A balcony starts at $14,403, about $686 a night.
Is $9,993 a good price for this sailing?
It is $1,995 above the lowest ocean view price we have recorded for this sailing since October 12, 2026 ($7,998 on October 12, 2026).
Which ports does it visit?
It sails from Montreal to San Juan and calls at Quebec City, Gaspe, Sydney, Halifax, Bar Harbor, Portland, Boston, Hamilton, St George, Gustavia St Barths and Virgin Gorda Island BVI, with 6 days at sea.
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