Windstar Cruises announced an expanded Canada & New England 2026 season, including a new 14-night itinerary and the return of several popular routes.
Known for its focus on smaller, less-traveled ports inaccessible to larger ships, Windstar will once again deploy its 312-passenger ship Star Pride during the peak autumn months (September and October) favored by travelers for viewing the region's stunning fall foliage.
New 14-Night Quebec & Newfoundland Adventure
The Quebec & Newfoundland Adventure is a roundtrip sailing from Montreal featuring an in-depth exploration of Newfoundland and Labrador, regions often overlooked by larger cruise lines. This itinerary includes rare stops at St. Pierre & Miquelon, French territories in North America, and Trois-Rivieres, with late-night departures offering extended opportunities for cultural and culinary exploration.
Windstar’s itinerary also revisits Red Bay, NL Labrador, and St John’s, NL Newfoundland, ports Windstar hasn’t featured since 2018. Highlights include an overnight stay in St John’s, offering time for guests to experience the city’s lively folk music scene, and a late-night departure from Quebec City, ideal for wine tastings at the Chateau Frontenac or guided tours through UNESCO-listed sites.
Southeast Canadian Explorations
The Southeast Canadian Explorations itinerary returns, sailing between Montreal and Boston (and the reverse). This voyage includes a stop at Cap aux Meules in the Madeleine Islands, where guests can enjoy a new lobster fishing tour, cheese tastings, brewery visits, and a bird-watching excursion focused on the region's striking caves and cliffs. For the first time since 2018, the itinerary will also call at Rockland, Maine, a hub for exploring picturesque lighthouses.
Greenland: North Atlantic Odyssey
Also returning for 2026 is the 14-night Greenland: North Atlantic Odyssey, a transatlantic journey from Reykjavik, Iceland, to Boston. Scenic cruising highlights include Prince Christian Sound and Tasermiut Fjord. The itinerary also features visits to remote Greenlandic villages such as Nanortalik and Narsaq, offering insight into Inuit culture. A late-night departure from Halifax, Nova Scotia, allows for in-depth exploration of the city’s Titanic history and local culinary scene.
Enhanced Shore Excursions and All-Inclusive Packages
Windstar's curated shore excursion program ensures guests can seamlessly book unique experiences at each port, ranging from historical tours to wildlife encounters. Additionally, the line has introduced an Early Booking Offer for its 2026 Canada & New England sailings. Guests booking by April 30th, 2025, will receive a complimentary upgrade to All-Inclusive fares, valued at US$99 per day. This package includes Wi-Fi, gratuities, unlimited beer, wine, and cocktails, as well as a US$200 onboard credit per stateroom.