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Chicago to Montreal

14 Days, 13 Nights | Price Starting at $2,299.50

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Join us in Chicago, the hub city with two international airports and more railway lines to more places than anywhere in the United States. But it’s the Great Lakes we’re focused on. Lake Michigan is our point of departure for 14 glorious days, sailing on Lake Huron, Lake Erie and Lake Ontario, to the St. Lawrence River and Canada, culminating in the fascinating, cosmopolitan city of Montreal.

We’ll visit the bustling shipbuilding port of Sturgeon Bay, WI, then hop to Mackinac Island, MI, where you can take an optional horse-drawn carriage ride (their main mode of transportation) before taking tea at the Grand Hotel. Next stops are Wyandotte MI, home to the Henry Ford Museum, and Cleveland, OH, famous for sports teams and the Rock and Roll Hall of Fame.

Our last stop stateside is Buffalo, NY, whose waterfront features friendly pubs, corner taverns and its own brewery. Or take an optional tour of Niagara Falls. From there we’ll cross Lake Ontario to the shores of Toronto before visiting Kingston, ON, the home of Fort Henry, and Upper Canada Village, where you’ll experience how people lived in a 19th century Canadian village.

But it all starts aboard the Grande Caribe as we glide past the gleaming giants that make up the Chicago skyline. This incredible trip touches 5 different States and 4 unique stops in Canada, in an uncrowded, casual atmosphere only our small ship cruises can provide.

Ports Visited

Waterways Navigated


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 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.


Optional sightseeing tours are at an additional cost and options are finalized 60 days prior to departure. All itineraries including ports, activities and routes are subject to change based on availability, weather, river, water levels and sea conditions. Valid passport required.

Pricing Per Person

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


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

Ship color key

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.
Sturgeon Bay
Mackinac Island lighthouse
Toronto sign
French cafe in Montreal

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