Small ship operator Windstar Cruises is adding a new itinerary to its Canada & New England season of sailings in 2026.
Small ships have an advantage when cruising in Canada and New England. This is because they can visit many smaller towns for a more relaxed, intimate style of exploration.
Smaller, scenic ports
Windstar Cruises is one operator with ability to visit primarily smaller, scenic ports where big ships don’t go. They have added a new itinerary for 2026. The line’s 312-guest Star Pride sails in the region during the main autumn colour months of September and October. This one for travellers who increasingly enjoy seeing nature’s vibrant autumn 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 time circumnavigating the region and its remote/hard-to-reach destinations. These include 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. Walk through Trois-Rivières’ Batiscan Park, with 400 acres of pristine wooded terrain brimming with waterfalls and meadows. Followed this with a guided evening tour of local culinary favourites.
New itinerary
The new 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 ship stays here 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, there is a 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. Here the new lobster fishing tour is sure to catch guests’ attention. The tour features a cheese tasting and brewery visits. There is also a bird-watcher’s dream boat cruise that dives into the history and geology of the archipelago’s many caves and cliffs.
Return to Rockland
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. The cruise offers 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. Halifax is a good port in which to enjoy 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 of September and 9th of October 11-night Southeast Canadian Explorations cruise start from £4,386 per person.
Prices for the 25th of September 14-night Quebec & Newfoundland Adventure cruise start from £5,176 per person.
Prices for the 31st of August 14-night Greenland: North Atlantic Odyssey cruise start from £4,749 per person.
Book a new itinerary cruise before 30th April 2025 and take advantage of a complimentary upgrade to the all -inclusive fare. This includes Wi-Fi, gratuities and unlimited beer, wine and cocktails, plus a $200 onboard credit per stateroom.