Windstar Cruises has announced the addition of a new itinerary in 2026 to its popular Canada & New England season of sailings which are northern autumn travel favourites.
The line’s 312-guest Star Pride motor yacht sails in the region during the prime autumn colour months of September and October for travellers looking to 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 spends ample time circumnavigating the region and it remote and hard-to-reach destinations, including the Madeleine Islands.
This journey offers two brand-new ports for Windstar in St. Pierre & Miquelon as well as Trois-Rivieres. Both ports offer late nights for additional exploration, like hiking through Trois-Rivieres’ Batiscan Park, with 400 acres of pristine wooded terrain brimming with waterfalls and meadows, followed by a guided evening tour of local culinary favourites.
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). The overnight visit makes it ideal for listening to folk music at the bars on Geroge 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 with a new lobster fishing tour along with cheese tasting and brewery visits, and a boat cruise that dives into the history and geology of the archipelago’s many caves and cliffs. Windstar also returns 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 and many artifacts, as well as imbibing in a food-centric pub crawl pouring local beer and wine.
Windstar curated a shore excursion program that makes 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 with a complimentary upgrade to All-Inclusive fares (value of US$150 a day), which includes Wi-Fi, gratuities, and unlimited beer, wine, and cocktails with an additional US$200 onboard credit per stateroom. The offer for 2026 sailings must be booked by 30 April 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,” Windstar president, Christopher Prelog, said.
“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 autumn colour splendour that this region is known for.”
