Circle the Great Lakes Multi-Day Trip Itineraries

Circle Lake Michigan

Circle Lake Michigan

Location: Wisconsin, Illinois, Indiana, Michigan
Duration: 8 days

Tour Itinerary: What to Expect

Discover the beauty and culture of the Great Lakes on an eight-day journey around Lake Michigan. Explore Milwaukee and Chicago, visit Michigan’s scenic sand dunes and charming waterfront towns, and enjoy two nights at the iconic Grand Hotel on Mackinac Island. Experience historic lighthouses, local museums, a fudge-tasting tour, and the crystal-clear waters of Kitch-iti-kipi. Back in Wisconsin, enjoy a behind-the-scenes tour of Lambeau Field, local wine, beer, and cheese tastings, and regional culinary favorites.


Lake Michigan by Land and Water

Discover Lake Michigan by Land and Water

Location: Wisconsin, Illinois, Indiana, Michigan
Duration: 7 days

Tour Itinerary: What to Expect

Explore the beauty of Lake Michigan on a seven-day journey through scenic coastlines, charming lakeside towns, and iconic attractions. Discover Milwaukee’s landmarks and Racine’s famous Kringle before exploring Chicago’s architecture and neighborhoods. Travel along Michigan’s shoreline to experience towering sand dunes, historic museums, and the storybook town of Charlevoix. Visit Mackinac Island for horse-drawn carriage rides, famous fudge tastings, and two nights at the iconic Grand Hotel. Enjoy a scenic crossing aboard the S.S. Badger steamship, with beautiful lake views along the way.


Circle Lake Ontario

Circle Lake Ontario

Location: Ontario, Canada, and New York, USA
Duration: 7 days

Tour Itinerary: What to Expect

Discover the history, culture, and natural beauty of Lake Ontario on a seven-day journey through Canada and New York. Explore Toronto’s iconic landmarks, visit Casa Loma, and dine above the skyline at the CN Tower. Experience Niagara Falls by boat and from behind the cascading water before crossing into the United States for vintage automobiles, an Erie Canal cruise, and the George Eastman Museum. Continue along Lake Ontario to explore maritime history in Oswego and Sackets Harbor, then cruise through the scenic 1000 Islands and tour magnificent Boldt Castle. Finish with historic Fort Henry in Kingston and a memorable visit to a local alpaca farm.

Simply in need of a Step-on Guide in the Great Lakes Region?

Our tour guides are professionally trained, each with a passion for the city and experience in group travel. Available on an hourly basis, our step-on guides will show off the port cities and sights of the Great Lakes to fit with your itinerary and needs.

Simply in need of a Step-on Guide in the Great Lakes Region?

Our tour guides are professionally trained, each with a passion for the city and experience in group travel. Available on an hourly basis, our step-on guides will show off the port cities and sights of the Great Lakes to fit with your itinerary and needs.

Check “Event Planning” Off Your List!


We do not ask for a deposit or signed contract, simply fill out the form below with as many details as possible.

We will contact you to confirm your booking. At this time, we ask you provide your tentative head count so we can confirm reservations with your selected locations.

Five days prior to your tour date we will need a final headcount, list of any allergies or dietary restrictions, and payment via credit card or check.

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