11-night Southeast Canadian Explorations Cruise From Boston, Massachusetts

Windstar

A historic castle fortress illuminated at night, located on a small island surrounded by calm water under a deep blue evening sky.
Windstar's Star Pride cruise ship sailing at sunset.
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Sailing Sep 14, 2026 - Sep 16, 2027

Your 11-night Canada/New England Cruise at a Glance

Sailings aboard Star Pride depart from Boston, Massachusetts with 8 stops in ports-of-call including Halifax (Nova Scotia), Portland, ME, and Montreal. The Cruise Web can help you find the best deals and stateroom prices on any of the 2 upcoming sailings in 2026 and 2027.

Departure Port

Boston, Massachusetts

Boston is home to great sports, great foods, and loads of history with the Freedom Trail and Harvard. Before you depart Boston, Massachusetts, we can help you plan travel and accommodations for your Canada/New England cruise.

Stops on your Canada/New England voyage will include Rockland on day 2 and Portland, ME on day 3. We can help you with excursions and making the most of any itinerary.

Cruise Ship

Star Pride

Star Pride, built in 1988 and refurbished in 2021, carries 312 passengers with a crew of 190.

Cruise Line

Windstar Cruises

Get away from the crowd and journey to unique destinations aboard Windstar’s intimate small ships. We can help you maximize deals on Canada/New England cruises aboard Star Pride or 7 of Windstar’s other ships.