Windstar Cruises is adding a new itinerary in 2026 to its popular Canada & New England season of sailings, which are fall travel favorites thanks to the line’s ability to visit many smaller, scenic ports where big ships don’t go. The line’s 312-guest motor yacht Star Pride sails in the region during the prime fall color months of September and October.
A new 14-night Quebec & Newfoundland Adventure sails roundtrip from Montreal with a rare in-depth cruise exploration of Newfoundland and Labrador. While most cruise lines include a quick stop or two, Windstar will spend ample time circumnavigating the region and its remote/hard-to-reach destinations, including the Madeleine Islands. The cruise offers two brand-new ports for Windstar in the French islands of St. Pierre & Miquelon as well as Trois-Rivières. Both ports offer late nights for additional exploration, like hiking through Trois-Rivières’ Batiscan Park, with 400 acres of pristine wooded terrain brimming with waterfalls and meadows, followed by a guided evening tour of local culinary favorites.
The itinerary also adds two ports Windstar hasn’t visited since 2018: the fishing village of Red Bay in Labrador as well as St. John’s, Newfoundland’s capital. An overnight stay there is ideal for visiting the bars on George Street and listening to folk music late into the night. An additional late night in Quebec City gives time for exploring UNESCO sites by day, wine tasting at the Chateau Frontenac with an expert sommelier.
Windstar has a curated shore excursion program making it easy for guests to book tours through the cruise line to see and experience a variety of attractions, including key highlights, in each port.
Windstar is also returning its Southeast Canadian Explorations sailing from Montreal to Boston and the reverse for 2026. Highlights include an overnight in Quebec City and smaller ports such as Cap aux Meules, with a new lobster fishing tour along with cheese tasting and brewery visits, Windstar will also return to Rockland, Maine on these sailings for the first time since 2018, meaning guests can visit the charming region’s many picturesque lighthouses.
The 14-night Greenland: North Atlantic Odyssey trans-ocean cruise from Reykjavik, Iceland to Boston also returns for 2026. A late night in Halifax means time to delve into the Titanic’s history/many artifacts, as well as imbibing in a food-centric pub crawl pouring local beer and wine.
Windstar is offering an early booking deal for the Canada & New England 2026 sailings with a complimentary upgrade to All-Inclusive fares (value of $99/day), which include Wi-Fi, gratuities, and unlimited beer, wine, and cocktails, plus $200 onboard credit per stateroom. The offer must be booked by April 30, 2025.
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