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 primarily 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 for travelers who increasingly enjoy seeing nature’s vibrant display.     

The 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 St. Pierre & Miquelon (the islands are a part of France) 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 – the capital of Newfoundland – which is an overnight visit, making it ideal for listening to folk music at the bars on George Street late into the night. An additional late night in Quebec City means plenty of time for exploring UNESCO sites by day, wine tasting at the Chateau Frontenac with an expert sommelier, and evening tours that highlight the city’s rich French influence. 

Windstar’s Southeast Canadian Explorations offering returns for the 2026 season sailing from Montreal to Boston and the reverse. Highlights include an overnight in Quebec City and smaller ports such as Cap aux Meules, where a new lobster fishing tour is sure to catch guests’ attention, along with cheese tasting + brewery visits, and a bird-watcher’s dream of a boat cruise that dives into the history and geology of the archipelago’s many caves and cliffs. 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, with scenic cruising of the Prince Christian Sound and Tasermiut Fjord, as well as chances to learn more about Inuit culture in the remote villages of Nanortalik and Narsaq. 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 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.  

Along with the announcement, Windstar is offering an Early Booking Offer for 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 for 2026 sailings must be booked by April 30, 2025.

“Our small ships have an advantage in Canada and New England because we can visit many smaller towns for a more relaxed, intimate style of exploration,” says Windstar’s President Christopher Prelog. “We’re very happy we can continue accessing many of these tiny ports along with expanding upon what our guests can experience by adding new tours, seaports, and an entirely new itinerary for 2026 – all paired with the magic of fall color splendor that this region is known for.” 

To plan a small ship cruise with Windstar or learn about booking offers, contact a travel advisor, reach out to Windstar Cruises by phone at 866-258-7245, or request a call by a Windstar vacation planner. Windstar has added a new online booking system for convenience.  Find more information on Windstar Cruises here.