Great Lakes Destinations - Multi-Day Trip Itineraries

Great Lakes Experience - Green Bay, Michigan’s Upper Peninsula & Mackinac Island

Great Lakes Experience: Green Bay, Michigan’s Upper Peninsula & Mackinac Island

Location: Wisconsin and Michigan
Duration: 8 days

Tour Overview: What to Expect

Experience the best of the Great Lakes on an eight-day adventure filled with natural wonders, local flavors, and Midwest history. Tour legendary Lambeau Field, sample Wisconsin wines, beers, and cheeses, and visit an alpaca ranch and the National Railroad Museum. Explore Michigan’s Upper Peninsula through historic towns, maritime museums, and the breathtaking Pictured Rocks, Tahquamenon Falls, and Kitch-iti-kipi spring. Meet rescued bears at Oswald’s Bear Ranch before heading to Mackinac Island for horse-drawn carriage rides, famous fudge tastings, and two nights at the elegant Grand Hotel.


Lake Superior and the Apostle Islands

Lake Superior and the Apostle Islands

Location: Minnesota, Ontario, Canada, and Wisconsin
Duration: 8 days

Tour Overview: What to Expect

Discover the natural beauty and cultural heritage of Lake Superior on an eight-day adventure through Minnesota, Canada, and Wisconsin. Explore Minneapolis, Duluth’s historic waterfront, and the scenic North Shore, with stops at iconic lighthouses, waterfalls, and the magnificent Glensheen Mansion. Travel to Thunder Bay for amethyst mining, local history, and stunning views of the Sleeping Giant. Enjoy a gondola ride over Lake Superior, explore traditional crafts, and sample homemade pie. Continue to the Apostle Islands for a guided visit to Madeline Island, then finish with freshwater fishing history and wine tasting in Stillwater.


Holland Tulip Fest

Holland Tulip Festival

Location: Milwaukee, Chicago, and Holland, Michigan
Duration: 6 days

Tour Overview: What to Expect

Celebrate spring at Holland’s famous Tulip Time Festival, surrounded by millions of colorful tulips and Dutch traditions. Explore Milwaukee and Chicago on guided city tours, sample Wisconsin’s famous Kringle, and enjoy an architectural boat cruise. In Holland, experience Dutch dancing, traditional cuisine, historic windmills, vibrant tulip gardens, and the lively Volksparade. Visit Nelis’ Dutch Village, watch artisans craft wooden bowls, and explore Frederik Meijer Gardens & Sculpture Park. Stroll through Veldheer’s Tulip Farm, home to millions of tulips, and enjoy an exhilarating dune buggy ride along Michigan’s sandy shores.


Detroit Thanksgiving

Thanksgiving in Detroit for America’s Parade

Location: Detroit, Michigan
Duration: 4 days

Tour Overview: What to Expect

Celebrate Thanksgiving in Detroit with a memorable getaway featuring America’s Thanksgiving Day Parade, festive markets, and delicious local cuisine. Enjoy reserved seating for the parade’s spectacular balloons, floats, marching bands, and performances, followed by a stroll through Detroit’s Christmas Market. Explore the Henry Ford Museum of American Innovation, discover Detroit’s iconic architecture on a guided city tour, and enjoy an Italian dinner at historic Amore da Roma. Along the way, savor Chicago favorites, share a traditional Thanksgiving feast, and visit Battle Creek to discover the history of Kellogg’s cereal before returning home.


Obama Library

Chicago & the Obama Presidential Center

Location: Chicago
Duration: 1 or 2 days

Tour Overview: What to Expect

Explore Chicago’s iconic landmarks and discover the Obama Presidential Center on a customizable one- or two-day getaway from Milwaukee or Chicago. Enjoy a guided city highlights tour, experience Chicago’s diverse neighborhoods, and savor an Italian dinner in Little Italy with a pasta-making demonstration. Visit the Obama Presidential Center on Chicago’s South Side to explore immersive museum exhibits, presidential memorabilia, public art installations, beautiful gardens, and panoramic skyline views from the Sky Room. Add a Chicago walking food tour or an overnight stay with dinner to complete your experience.


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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