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Chicago to Montreal

14 Day, 13 Day | Price Starting at $4,599.00

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Ten thousand years ago, the last great glaciers retreated, leaving the legacy of the Great Lakes. Cruise through all the wild splendor, rugged wilderness and majesty of the Northern lakes, canals and rivers from Chicago to Montreal.

Your journey begins among the distinct architecture in Chicago. Arrive next in Sturgeon Bay, WI where artists meet shipbuilders to create a unique waterfront culture. At Mackinac Island, sip tea at the Grand Hotel before a horse-drawn carriage brings you back to the ship. Museums abound between Wyandotte and Cleveland. From the Henry Ford Museum of Dearborn to the Rock and Roll Hall of Fame, culture and camp collide for a light, well-rounded experience. Then, in Buffalo, witness the awe-inspiring Niagara Falls - the most powerful waterfall in North America. Cruise now, into Ontario where the contrast of modern Toronto compliments the grand heritage feel in Kingston. Go back in time to the Gilded Age at Upper Canada Village before reaching Montreal where you will conclude your journey.

Ports Visited

Waterways Navigated


Chicago, IL

Embark in Chicago, whose architecturally renowned skyline is juxtaposed against Lake Michigan creating a fusion of serene vistas and exciting cityscapes, symbolizing this entire journey.

Sturgeon Bay, WI

In Wisconsin’s Door County, visit idyllic Sturgeon Bay, a shipbuilding port where historic lighthouses and yachts create a striking seascape. An optional morning tour of this coastal community begins with a local wine tasting, and continues to the Door County Maritime Museum, where you can board a 1930s tugboat or a steamship from 1907.

Mackinac Island, MI

Home to multitudes of horses but no cars; sip tea on the porch of the Grand Hotel. Admire the perfectly preserved homes and architecture during an optional tour of the island. Stop by the Wings of Mackinac Butterfly Conservatory and Surrey Hill Square Carriage Museum to get the full Mackinac experience.

Wyandotte, MI

Enjoy the Henry Ford Museum of Dearborn, home to 12 acres of historical artifacts, including JFK's limousine and the Rosa Parks bus. Other highlights include the Wright Brother's bicycle shop and Thomas Edison's lab.

Cleveland, OH

Known as the "North Coast" for it's proximity to Lake Erie. Explore this great lakes metropolis during a city tour or visit the Rock and Roll Hall of Fame! 

Buffalo, NY

Located at the head of the Niagara River, Buffalo, NY is known for its sports, snow, and special sauce. Admire breathtaking views of world-famous Niagara Falls during an optional tour.

Toronto, ON

Discover a cultural treasure trove, with more than 100 cultures creating a uniquely, diverse city. This global city, is a center for business, finance, and arts. It is also recognized as one of the most multicultural and cosmopolitan cities in the world.

Kingston, ON

Nicknamed the "Limestone City" for the many heritage buildings constructed using local limestone, Kingston is a city to behind at the half-way point between Montreal and Toronto. Here, you may get a sense of early Canadian history during a visit to Fort Henry.

Upper Canada Village

Upper Canada Village offers a magical tour that transports you back in time to the 1860s. View the authentic buildings that make up the village, and learn about all that went on here in the Guilded Age. Founded in 1961, Upper Canada Village is one of the largest living-history sites in Canada. Enjoy this depiction of life in a rural English Canadian setting during the year 1866.

Montreal, QC

Where cosmopolitan modern art and architecture meet traditional cobblestone streets and French cafes. You may choose an optional city tour that includes Old Montreal or explore this historic and enchanting city at your leisure.


Category I
Category II
Category III
Category IV
Category III Singles
Port Charges


Optional sightseeing tours are at an additional cost. All itineraries including ports, activities and routes are subject to change based on availability, weather, river, water levels and sea conditions.

Departure Dates

Embark: Chicago, IL
Aug 28, 2019
Disembark: Montreal, QC
Sep 10, 2019

The Ship Grande Caribe

Your small ship adventure is a personal and casual one- like cruising on a friend’s yacht.

Hover over the cabin to view the room layout

Deck Plans

Category I Cabin

Category II Cabin

Category III Cabin

Category IV Cabin

Cabin Bathroom

Includes shampoo, conditioner, body wash, hair dryer, fresh towels daily

Clock tower in Buffalo, NY
Passenger at the Chicago Bean.
View of Kingston on the Hudson River.
Flag at the Mackinac Island Grand Hotel.
Mackinac Island from the vessel's top deck.
Resident riding bikes around Mackinac Island.

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