Sarah Bretz, ContributorWindstar Cruises has announced that it is adding a new itinerary to its 2026 Canada and New England season. In September and October, the line’s motor yacht Star Pride will sail in the region, offering beautiful views of the fall foliage during peak season.
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 just a quick stop or two, Windstar will spend quite a bit of time circumnavigating the region and its remote destinations, including the Madeleine Islands.
Two New Ports
The cruise includes two brand-new ports for Windstar: St. Pierre & Miquelon (part of France) and Trois-Rivières. The ship will stay late into the night, allowing guests to to hike 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.
Two Returning Ports
The itinerary also adds two ports that 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 latter 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 itinerary will return 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, which will feature a new lobster fishing tour. There will also be 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.
The cruise line will also return to Rockland, Maine on these sailings for the first time since 2018, meaning guests can visit the charming region’s many lighthouses.
The 14-night Greenland: North Atlantic Odyssey trans-ocean cruise from Reykjavik, Iceland to Boston will also return in 2026, offering scenic cruising of the Prince Christian Sound and Tasermiut Fjord and visits to the remote villages of Nanortalik and Narsaq. A late night in Halifax allows time to delve into the Titanic’s history and artifacts, as well as enjoying a food-centric pub crawl featuring local beer and wine.
Early Booking Offer
Windstar Cruises is offering an Early Booking Offer for 2026 Canada & New England sailings with a complimentary upgrade to All-Inclusive fares (a value of $99 per day) that includes wifi, gratuities, and unlimited beer, wine, and cocktails, plus $200 in 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.”
Comments
Would you take a voyage to Canada and New England with Windstar Cruises? Have you ever cruised in this region and if so, with what line? Drop us an anchor below and let us know!
