Windstar Introduces Autumn 2026 Canada & New England Season With New Itinerary, First-Time Ports & An Early Booking Offer
Windstar Cruises is adding a new itinerary in 2026 to its popular Canada & New England season of sailings which are autumn travel favourites 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 main autumn colour months of September and October for travellers 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 as well as Trois-Rivières. Both ports offer late nights for additional exploration such as 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 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 – 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 to explore 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 in 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 and 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 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 enjoying a food-centric pub crawl pouring local beer and wine.
Windstar has a curated shore excursion programme making it easy for guests to book tours to see and experience a variety of attractions and key highlights in each port.
- Prices for the 14th September and 9th October 11-night Southeast Canadian Explorations cruise start from £4,386 per person.
- Prices for the 25th September 14-night Quebec & Newfoundland Adventure cruise start from £5,176 per person.
- Prices for the 31st August 14-night Greenland: North Atlantic Odyssey cruise start from £4,749 per person.
Windstar Cruises has introduced an early booking offer for Canada & New England 2026 sailings with a complimentary upgrade to the all -inclusive fare (value of £81 per person per day) which includes Wi-Fi, gratuities and unlimited beer, wine and cocktails, plus $200 onboard credit per stateroom. The offer is valid on all 2026 Canada & New England sailings if booked by 30th 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,” 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 colour splendour that this region is known for.”
Learn more about Windstar Cruises
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