Windstar is adding a new itinerary in 2026 to its Canada & New England season of sailings.

The line announced in a press release that the line’s 312-guest Star Pride sails in the region during the months of September and October.

The new 14-night Quebec & Newfoundland Adventure sails roundtrip from Montreal with a focus on exploration of Newfoundland and Labrador.

Windstar will circumnavigate the region and destinations including Madeleine Island.

The cruise offers two brand-new ports for Windstar in St. Pierre & Miquelon (the islands are part of France) as well as Trois-Rivières. Both ports offer late nights for additional exploration, like hiking through Trois-Rivières’ Batiscan Park, followed by a guided evening tour of local culinary favorites.

According to Windstar, the itinerary has added two ports that Windstar last visited in 2018: the fishing village of Red Bay in Labrador and St. John’s, the capital of Newfoundland, which is an overnight visit. It also now includes an additional late night in Quebec City.

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, which offers a lobster fishing tour, cheese tasting and brewery visits, and a boat cruise that dives into the history and geology of the archipelago’s caves and cliffs.

Windstar added that it will return to Rockland, Maine on these sailings for the first time since 2018.

The 14-night Greenland: North Atlantic Odyssey trans-ocean cruise from Reykjavik, Iceland, to Boston also returns for 2026, with cruising of the Prince Christian Sound and Tasermiut Fjord, and offers chances to learn more about Inuit culture in the villages of Nanortalik and Narsaq.

There is also a late night in Halifax, delving into the Titanic’s artifacts and providing a food-centric pub crawl pouring local beer and wine.

Windstar added that it has a curated shore excursion program, making it easy for guests to book tours through the cruise line. It is offering an Early Booking Offer for Canada & New England 2026 sailings with a complimentary upgrade to All-Inclusive fares (value of $99/day). Offers for 2026 sailings must be booked by April 30, 2025.