Great Lakes Inn-Sider

  • Chicago + 1 more
  • Self Drive Ideas
  • 13
from  £1,179pp
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The highlights of the Great Lakes and stay in unique boutique hotels. Starting from Chicago, you will discover Door County, Middleton, Winona, Minneapolis, the beautiful Apostle Islands and the beautiful Mackinac Island.

A Free Personalised Road Book is included as standard with our Self Drive itineraries. 


Please note: – This is a suggested itinerary only and is intended to give an overview of what is possible. All of our holiday itineraries are fully customisable and can be tailor-made to suit your own individual requirements.  If you would like to start in a different destination, use specific hotel accommodation, include an extra night here, a side-trip there and/or include tickets to an event please let your Discover North America travel specialist know. They’ll also book you the best value flights to ensure a seamless holiday experience.


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Day 1 Chicago

Arrive Chicago. This evening, enjoy Chicago’s many restaurants, stroll along the shore of Lake Michigan or jive to the beat at a jazz or blues club.

Day 2 Chicago-Milwaukee-Ephraim (259mi/417km)

This morning depart for Door County, visiting Milwaukee en route. Once known almost exclusively as a brewing powerhouse, the city now boasts the beautiful Milwaukee Riverwalk and Milwaukee Art Museum, with its architecturally impressive addition designed by Santiago Calatrava. The modernist building is shaped like a floating cross, with wings opening and closing from a central base. Even people who’ve never been on a motorcycle will enjoy the Harley-Davidson Museum. Exhibits tell the stories of the extraordinary people, products, history and culture of Harley-Davidson and of-course the fantastic motorcycle collection will captivate all. Continue on to Door County, the “Cape Cod of the Midwest”. With five state parks, ten lighthouses and over 300 miles of shoreline, this 75-mile long peninsula was named one of the top ten vacation destinations in North America. Spend the next two nights in a quaint village where shops and galleries are set in century-old barns, rustic log cabins and vintage homes.

Day 3 Door County

Spend the day hunting for treasures in one-of-a-kind shops, galleries, museums & lighthouses. Pick a pail of ripe Door County cherries in the summer or a basket of crunchy apples in fall. Or perhaps enjoy Door County on the water. Charter a boat for fishing or for general relaxing, take a kayak or sailboat tour, scuba diving or jet skiing excursion.

Day 4 Door County-Middleton (257mi/414km)

Travel west to Middleton, visiting Baraboo en route. Baraboo is home to the Circus World Museum, the former headquarters and winter home of the Ringling Brothers circus and now the largest library of circus information in the United States. This living museum has a collection of circus wagons, and occasionally hosts the Great Circus Parade of these artifacts through the streets of Baraboo. The Al. Ringling Theatre is an active landmark in the city. This grand scale movie palace is larger and more elaborate than one would normally find in a town the size of Baraboo, owing to the financial assistance of the Ringling family. The Al Ringling home still exists and is maintained in good condition. Continue into Middleton for the night.

Day 5 Middleton-Winona (129mi/207km)

Today, visit two premier attractions in Spring Green, the Taliesin Estate and House on the Rock. Frank Lloyd Wright, America’s premier architect and Wisconsin’s native son considered Spring Green his home, and he built and created an environment both beautiful and inspirational. House on the Rock has room after room of some of the world’s most unique and eclectic collections from the smallest detail of an intricately furnished doll house collection to the world’s largest indoor carousel. Each exhibit is filled with the exotic, the majestic, and the unexpected. Then travel to Winona in the afternoon. Often likened to the Rhine in Germany, Winona is a lush valley town on the banks of the Mississippi River and is surrounded by natural beauty. Spend the evening at a “Destination” Bed & Breakfast with elegant turn-of-the-century craftsmanship, magnificently restored to its 1886 Victorian splendor.

Day 6 Winona-Minneapolis (148mi/238km)

Drive along the mighty Mississippi today to the Twin Cities. Here you’ll find a variety of districts as things to do. Visit the Riverfront District, the historic "birthplace of Minneapolis with an eclectic collection of historic buildings, scenic parks, cultural venues, dining, and shopping, with the inspiring St. Anthony Falls on the Mississippi River as a dramatic backdrop. Or do some shopping at the Mall of America in neighboring Bloomington, the largest mall in the country.

Day 7 Minneapolis-Bayfield (208mi/373km)

Beautiful Bayfield, a relaxing small town with plenty to do serves as the gateway to the Apostle Islands National Lakeshore, a National Park that includes 21 beautiful and enchanting wilderness islands and over 12 miles of scenic peninsula shoreline. In fact, the Apostle Islands were recently featured as a “Top Place to Visit” by National Geographic Explorer. Widely known for having one of the nation’s finest collections of historic lighthouses, Apostle Islands National Lakeshore also offers the opportunity to roam through awe-inspiring old growth forests that Ojibwe Indians call home. Stay for two nights in Bayfield's first Bed and Breakfast, best described as a small elegant hotel with unique furnishings and stunning stained glass windows.

Day 8 Bayfield-Apostle Islands-Madeline Island-Bayfield

Today explore the Apostle Islands National Lakeshore and especially Madeline Island , the only one of the Apostle Islands not included in the national lakeshore, although a portion of the island is protected as Big Bay State Park. The island is accessible by ferry and has shops, restaurants and other establishments that make it popular with visitors to the national lakeshore.

Day 9 Bayfield-Marquette (205mi/330km)

Enjoy Bayfield’s bountiful offerings this morning before cutting across the Upper Peninsula to Marquette. The U.P. as it’s known is bounded on the north by Lake Superior, on the east by the St. Mary's River, on the southeast by Lake Michigan and Lake Huron, and on the southwest by Wisconsin. Besides its extensive coastline on the Great Lakes, large tracts of state and national forests, cedar swamps, and more than 150 waterfalls, make it a hub for boating, fishing, hiking opportunities, and snowmobiling in winter. In Marquette, one can find familiar European and Scandinavian fare, such as the pasty brought to the region by Cornish miners, and juustoa (squeeky cheese) and sauna makkara (a ring-bologna sausage) brought to the region by the Finnish. Stay the night in Marquette’s most historic inn.

Day 10 Marquette-Mackinac Island (171mi/274km)

Travel to St Ignace, park your car and board the ferry for the 20 minute hi-speed ferry to the island where Victorian sensibility predominates. Bicycles and horse-drawn carriages are the modes of transportation on this island in the straits of Mackinac where the upper peninsula of Michigan meets the lower peninsula. Take a horse and carriage ride this afternoon to familiarize yourself with this delightful island measuring only 3.8miles (9.82) in land area.

Day 11 Mackinac Island

Today you may want to take a self guided hiking tour or rent a bicycle to tour sites such as Arch Rock, Skull Cave, Sugarloaf, British Landing, Devil's Kitchen and the Beach of a Bazillion Beautiful Skipping Stones, or just sit back, relax and eat the fudge the island is famous for.

Day 12 Mackinac Island-Saugatuck (293mi/472km)

Saugatuck is one of Michigan's favorite beach towns and has evolved to become a place of serene beauty and lively outdoor recreation. Here one will find history, culture and festivals on the shores of Lake Michigan. Be sure to take time to stroll its’ boardwalk, beautiful beaches, and visit its’ lighthouses.

Day 13 Saugatuck-Chicago (140mi/225km)

Have a leisurely morning in Saugatuck or set out to visit the charming beach communities of Holland and Grand Haven en route to Chicago for your departure.