New 2026 Canada & New England Voyages

Explore New Worlds Close to Home

Experience Windstar’s popular and new 2026 itineraries in Canada & New England aboard our all-suite Star Pride, which serves just 312 guests.

Our 2026 season brings the return of our popular Southeast Canadian Explorations. Overnight in Quebec City, explore historic sites in Boston and visit small fishing towns like Cap-aux-Meules. 

Embark on our trans-oceanic,14-night Greenland: North Atlantic Odyssey cruise. This scenic adventure finds you crossing Prince Christian Sound and Tasermiut Fjord. See charming colonial towns and visit remote villages to learn about Inuit culture. 

We’ve also added a new 14-night Quebec and Newfoundland Adventure itinerary. This roundtrip Montreal adventure includes a new overnight in St. John, one of the oldest cities in North America. We’ll also call on the new port of St. Pierre & Miquelon, the last French territory on the continent.

Reserve a 2026 Canada & New England cruise by April 30, 2025, and enjoy a complimentary All-Inclusive experience — featuring Wi-Fi, unlimited select wine, beer and cocktails, and all gratuities — plus up to $200 onboard credit per stateroom.

See terms and conditions

 
The neighborhood of Old Quebec is home to the only fortified city walls north of Mexico.
The village of Cap-aux-Meules is famous for its stunning red sandstone cliffs shaped by the wind and sea.
The eight-island archipelago of Saint-Pierre and Miquelon is the only French territory left in North America.
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Star Collector: North Atlantic Explorer

Port to port
Reykjavik to Boston
Departure
August 24, 2026
Duration
21 Days
Ship
Star Pride
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$8,899 per guest
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$8,899USD per guest

Star Collector: Greenland Fjords, Canadian Maritimes

Port to port
Reykjavik to Montreal
Departure
August 31, 2026
Duration
25 Days
Ship
Star Pride
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Cruise only
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$5,899 per guest
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All-inclusive
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$5,899USD per guest

Greenland: North Atlantic Odyssey

Port to port
Reykjavik to Boston
Departure
August 31, 2026
Duration
14 Days
Ship
Star Pride
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Cruise only
from
$5,299 per guest
?
All-inclusive
from
$5,299USD per guest

Southeast Canadian Explorations

Port to port
Boston to Montreal
Departure
September 14, 2026
Duration
11 Days
Ship
Star Pride
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Cruise only
from
$9,299 per guest
?
All-inclusive
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$9,299USD per guest

Star Collector: Autumn in Newfoundland and New England

Port to port
Boston to Montreal
Departure
September 14, 2026
Duration
25 Days
Ship
Star Pride
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Cruise only
from
$9,299 per guest
?
All-inclusive
from
$9,299USD per guest

Star Collector: Autumn in Newfoundland and New England

Port to port
Montreal to Boston
Departure
September 25, 2026
Duration
25 Days
Ship
Star Pride
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Cruise only
from
$6,399 per guest
?
All-inclusive
from
$6,399USD per guest

Quebec and Newfoundland Adventure

Port to port
Montreal to Montreal
Departure
September 25, 2026
Duration
14 Days
Ship
Star Pride
?
Cruise only
from
$5,299 per guest
?
All-inclusive
from
$5,299USD per guest

Southeast Canadian Explorations

Port to port
Montreal to Boston
Departure
October 9, 2026
Duration
11 Days
Ship
Star Pride
?
Cruise only
from
$6,099 per guest
?
All-inclusive
from
$6,099USD per guest

Star Collector: Fall Leaves & Caribbean Breezes

Port to port
Montreal to San Juan
Departure
October 9, 2026
Duration
19 Days
Ship
Star Pride
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Cruise only
from
$2,399 per guest
?
All-inclusive
from
$2,399USD per guest

Bermuda Bliss

Port to port
Boston to San Juan
Departure
October 20, 2026
Duration
8 Days
Ship
Star Pride