Visit Chicago, Detroit, Saugatuck, Holland, Sleeping Bear Dunes, Mackinac Island, Pictured Rocks National Lakeshore, Door Peninsula and Milwaukee.
Starting in Chicago… You’ll explore…
Key road trip highlights:
Share this trip
We’ll suggest properties to match your preferred budget, be it low-cost, mid-range or high-end luxury that you’re looking for. We can also mix it up so you’ll experience a range of standards and experiences along your road trip.
All of our American road trips can be tailored to meet your requirements. Do you have more or less than 14 days for your road trip? No problem, we can bolt on extra nights to allow more time to explore or shorten the number of destinations as required. Just let us know when requesting your quote.
Begin this classic Great Lakes road trip by spending three nights and two thrilling days exploring the iconic city of Chicago. Many visitors start their stay by enjoying Chicago’s famous pizza or by going to the top of Willis Tower to watch the sunset over the city. You’ll collect your car when you leave Chicago to tour around the Great Lakes region. For now, you’ll be exploring Chicago by foot, L-Train, or Uber as you move from one world-class attraction to another.
Most visitors to Chicago head straight to the ‘Magnificent Mile’, a vibrant, bustling area which is home to upscale shops, trendy restaurants and posh hotels. Landmarks include the historic Chicago Water Tower, the neo-Gothic Tribune Tower and the 100-story Hancock Center, which has a rooftop observation deck called 360 Chicago. Spend the rest of the day exploring some of the other attractions found north of the Chicago River. These include Navy Pier, Wrigley Field and the beaches along Lake Michigan’s shoreline.
On your final full day in Chicago, we recommend that you spend the day visiting the city’s attractions that are located south of the Chicago River. Some of America’s very best museums are found here, including the Art Institute, the Alder Planetarium, and the Field Museum of Natural History. Be sure to stroll around Millennium Park; you’ll find world-famous outdoor artworks like Cloud Gate and Crown Fountain for those all-important Social Media snaps. Lastly, before leaving town, consider spending an evening partying at Buddy Guy’s Legends Nightclub.
Collect your car and cruise around the southern shoreline of Lake Michigan on your way to Indiana Dunes National Park and neighbouring Indiana Dunes State Park (pictured). Here, you’ll enjoy lovely hikes along Lake Michigan’s beaches and over the mighty sand dunes that are found here. Next, you’ll jump back in the car and head east to pretty Ann Arbor and then Motor City – Detroit. During a summer evening, you can catch a baseball game or enjoy lively drinks, food, and even gambling in Greektown.
Detroit has two world-class visit museums. Music fans absolutely must head to the Motown Museum, Home of Hitsville, USA. You’ll need to book ahead, but once inside, you’ll be guided through the house where Barry Gordon created the Motown sound and record label, which dominated the airwaves during the 1960s and 1970s. Later that day, we recommend you head over to Detroit’s other world-class museum – The Henry Ford. This isn’t just about cars; although there are many iconic cars, this place contains all manner of exhibits based on American innovation.
Cruise west to the Gold Coast of Lake Michigan, and then head north to the adorable small towns of Douglas and Saugatuck. The Great Lakes area is packed with picturesque small towns. Saugatuck, in particular, is a jewel and one of the prettiest places in the entire Great Lakes region.
Spend the morning discovering the charming streets, shops and restaurants dotted around beautiful Saugatuck. After lunch at a local restaurant, like The Butler, consider crossing the Kalamazoo River on the adorable Saugatuck Chain Ferry and climb Mount Baldhead to enjoy far-reaching views of Lake Michigan. Felling lazy, then forget Mount Baldhead and hire a retro boat to explore the river and Lake Michigan from the water.
Sleeping Bear Dunes National Lakeshore is managed by the National Park Service, and thus, it offers a pristine environment of outstanding natural beauty for visitors to the Great Lakes region. Sleeping Bear is centred around enormous sand dunes. One massive dune, in particular, used to resemble a “Mother Bear” sleeping on the ground, with her two cubs made up of two islands that lie just off the shoreline.
Energetic visitors can opt to walk down and then back up the biggest sand dune you’ve ever seen (pictured). The rest of us can drive to the top and sit and watch all the energetic people regret their decision to walk down to the shoreline. What fun. In the afternoon, you can explore less challenging hikes through woodland and more manageable sand dunes.
Leave Sleeping Bear Dunes behind and cruise through lovely Great Lake towns like Leland, Petoskey, and Harbor Springs on your way to Mackinaw City. Park your car on the shore ofjump on a ferry to one of the Great Lakes’ foremost destinations— Lake Huron and Mackinac Island. This special island banned cars as a clever marketing gimmick back in the day. Today, the benefits are clear: charming horse-drawn taxis and tourists on bicycles make this a unique environment in which to spend two relaxing days.
Start your day with a pancake breakfast, then rent a bike and enjoy a flat 8-mile ride around this pretty little island. After lunch, you can visit the Historic Fort and then stroll over to find Sugarloaf Rock and Arch Rock. Next, find a couple of Adirondack chairs and a bottle of wine and watch the sunset from your hotel porch. Complete your day with a delicious fish dinner at one of the numerous restaurants found on Lake Shore Drive.
After two days without your beloved rental car, it’s time to get behind the wheel and cruise across the 5-mile-long Mackinac Bridge to explore the scenic roads of the U.P. – the Upper Peninsula of Michigan. Suppose you decide to follow the suggested route in your travel pack. In that case, your first stop will be Tahquamenon Falls (the largest in Michigan) before heading west to explore the wonderful Pictured Rocks area.
Enter the State of Wisconsin and cruise around Green Bay to find the lovely Door Peninsula. The Door Peninsula is packed with charming lake houses, many of which are second homes to wealthy individuals from Milwaukee, Green Bay and even Chicago. This is a beautiful place to relax and unwind as you near the end of this Great Lakes road trip adventure.
Head south for 24 hours in Milwaukee. Enjoy breweries, fish dinners (fish and chips to us) and the fine food found at the Milwaukee Public Market. Interested in motorbikes? Then, be sure to head over to the Harley-Davidson Museum to learn about the story of the “hog”. Milwaukee’s other highlights include the Milwaukee Public Museum, the “Bronze Fonz” statue and the epic architecture and art collection of the Milwaukee Art Museum.
Share this trip
You’ll find answers to most of your questions right here. If you still need assistance, Feel free to get in touch, and we’ll be sure to get back to you promptly!
Not a problem. If you are lucky enough to have extra time to explore more places or add more rest days, then just let us know and we’ll adjust your trip to match your preferred timescale.
We strongly advise that you purchase travel insurance for your holiday to cover you against medical expenses, theft and other financial costs. Should you need to cancel before travelling, some insurance policies may pay out for any loss of funds that have been paid to us and which cannot be refunded under our cancellation policy.
Many of our trips have a different end destination than the starting point, so this is not a problem. Please note a fee sometimes applies for one-way rentals between other regions or states, which will be paid to the supplier directly when collecting the vehicle. We’ll endeavour to inform you of this charge within your quote.
No, far from it. We work with a range of properties from 3* to 5*, so we can adapt the trip to match most budgets. We have access to rooms in more than 800 hotels, motels, lodges and B&Bs across North America.
The minimum age to rent a car is 21 in the United States or Canada, although, in addition, any drivers under 25 years of age will generally incur a surcharge.
Please use the form below to request a quote from our team. Fields marked with an * are mandatory. Please note that we currently only serve customers based in the UK & The EU.
Not quite what you’re looking for? Get in touch to discuss your Bespoke Road Trip plans, or check out these similar road trip itineraries…
ARTCo customers can be confident that we only work with the very best service providers, such as Virgin Atlantic, British Airways and Alamo. Any payments made to us are fully protected via the government’s ATOL scheme (Flight packages) or Financial Failure Insurance (Non-Flight Packages).
