Take in three of the Great Lakes and a string of classic Midwest towns on this four-day small-group loop out of Chicago. Travel up the western shore of Lake Michigan through Milwaukee and Green Bay into the wild Upper Peninsula, where the colorful cliffs of Pictured Rocks and the amber cascades of Tahquamenon Falls line Lake Superior. Cross to car-free Mackinac Island, one of the most beautiful islands in the world, for a horse-drawn carriage ride, then wind down through scenic Traverse City and the Dutch-themed town of Holland before returning to Chicago. It’s a relaxed, scenery-rich way to see the heart of the Great Lakes.
07:30Departure Chicago: Chinatown;218 W Cermak Rd, Chicago, IL 60616;(After06/09/2025) 08:00Departure Chicago: Millennium Park Welcome Center;201 E Randolph St, Chicago, IL 60601;(before06/09/2025)
We will start our first day Milwaukee, the largest industrial city in Wisconsin visiting Harley-Davidson Museum. After the museum, we will head to the famous Milwaukee Public Market located in Milwaukee’s historic Third Wards. In the Milwaukee Public Market, you are going to see a variety of Wisconsin specialty foods, including cheese and sausage. Next, we will continue driving north along the Lake Michigan. We will enjoy our dinner here. After dinner, we will head to the hotel. Itinerary: Day 1: Chicago → Milwaukee → Harley-Davidson Museum (optional, 60 min) → Milwaukee Public Market (60 min) → Green Bay (30 min) → Escanaba
Harley-Davidson Museum (60 min): We set off from Chicago and head up into Wisconsin to Milwaukee, the state’s largest city and an industrial powerhouse. If you’d like, visit the Harley-Davidson Museum on the banks of the Menomonee River, home to more than 450 motorcycles from every era and considered the spiritual home of the brand.
Milwaukee Public Market (60 min): Stop for lunch at the Milwaukee Public Market, a lively indoor hall packed with specialty food stalls, fresh produce, and local makers selling jewelry, crafts, and more. It’s a favorite gathering spot for locals and a must-see for visitors.
Continue to Green Bay, a port city on the shores of Lake Michigan at the mouth of the Fox River. A stop on the St. Lawrence Seaway, it’s long been a major distribution hub for the region.
We finish the day in Escanaba, on Michigan’s Upper Peninsula, where we check in for the night.
Sit back and take in all the magnificent views as we take you through Michigan! We will examine Lake Superior Picture Rocks National Lakeshore and the Tahquamenon Fall. We will arrive in St. Sainte Marie in the afternoon where we can enjoy the journey between Lake Superior and Lake Huron. This will be an unforgettable experience that you don’t want to miss out on. Itinerary: Day 2: Escanaba → Pictured Rocks National Lakeshore In-depth Tour [Miner’s Castle (35 min) → Miner’s Beach (35 min) → Tahquamenon Falls (90 min)] → Point Iroquois Lighthouse (30 min) → Soo Locks (30 min) → St. Ignace
Pictured Rocks National Lakeshore In-depth Tour: We spend the morning along Lake Superior, the world’s largest freshwater lake, on an in-depth tour of the Pictured Rocks shoreline. Pictured Rocks National Lakeshore In-depth Tour [Miner’s Castle (35 min) → Miner’s Beach (35 min) → Tahquamenon Falls (90 min)]
At Miner’s Castle you take in the famous multicolored cliffs and the lake’s layered bands of color. Just up the shore, Miner’s Beach offers a spectacular view back toward the Pictured Rocks.
The tour finishes at Tahquamenon Falls, the “Amber Twin Falls,” whose bronze-tinted water is especially striking in the light.
A short stop at the historic Point Iroquois Lighthouse, where you can look out over the meeting point of Lake Superior and Lake Huron.
Next are the Soo Locks on the St. Marys River, the engineering marvel that lets ships pass between Lake Superior and the lower Great Lakes, right at the border between Michigan’s Upper Peninsula and Ontario.
St. Ignace → Mackinac Island (4 hr) → Traverse City (30 min)
Mackinac Island (4 hr): Take a scenic ferry across to Mackinac Island, once named one of the world’s ten most beautiful islands and a true jewel of the Great Lakes. On the way you’ll pass the five-mile Mackinac Bridge linking Michigan’s two peninsulas. The island has no cars, so you explore on foot or by horse-drawn carriage, taking in well-preserved colonial architecture, lush scenery, and the island’s famous fudge.
Traverse City (30 min): In the evening we head to Traverse City, tucked into the Lower Peninsula on the shores of Lake Michigan, known for its beaches, award-winning wineries, and easygoing charm.
e leave Traverse City early and travel south along the eastern shore of Lake Michigan to Holland, a town founded by Dutch immigrants and dotted with Dutch-style buildings that give it a distinctly European feel. Itinerary: Traverse City → Holland → Windmill Island (60 min) → Gilmore Car Museum (60 min) → Chicago
Windmill Island (60 min): Visit Windmill Island Gardens, home to “De Zwaan,” an authentic 250-year-old windmill shipped over from the Netherlands, set among colorful gardens with plenty of time to wander.
Gilmore Car Museum (60 min): Then stop at the Gilmore Car Museum, which holds the state’s largest collection of classic and vintage automobiles, with cars spanning the decades from 1890 to 1960.
From there it’s the drive back to Chicago, wrapping up four days around the Great Lakes.
For a full refund, cancel at least 24 hours before the scheduled departure time.
You can cancel up to 24 hours in advance of the experience for a full refund.
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