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2023-12-25
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Road Trip Around Lake Michigan Itinerary

Lake Michigan Grand Tour Itinerary

Embark on an unforgettable road trip around the majestic Lake Michigan, starting and ending in the bustling city of Chicago, IL. Your adventure begins in the Windy City, where you can delve into its rich cultural offerings, visit iconic landmarks like The Bean, and enjoy the city's famed deep-dish pizza. Head north to the charming city of Evanston, IL, a cultural hub with beautiful lakeside views and unique shopping experiences.

Continue your journey to Milwaukee, WI, a city renowned for its breweries and rich German heritage. Explore the historic Harley-Davidson Museum and the Milwaukee Art Museum's breathtaking architecture. From there, make your way to Sheboygan, WI, the 'Malibu of the Midwest,' offering great surfing and a range of outdoor activities.

Next on the itinerary is Green Bay, WI, the hometown of the Green Bay Packers. Fans can soak up the sports history at Lambeau Field and enjoy other local attractions. Travelling further north, arrive at Mackinaw City, MI, the gateway to Mackinac Island, where you can explore historical sites and enjoy outdoor activities amidst stunning backdrops.

Your tour won't be complete without visiting Traverse City, MI, the cherry capital with its scenic vineyards and access to Sleeping Bear Dunes. Ludington, MI, offers stunning state parks and lighthouses along with serene beaches. Muskegon, MI, promises cultural and historical explorations with its museums and maritime history.

Conclude your trip by returning to Chicago, IL, where you can round off your experience by revisiting favorite spots or discovering new attractions in this ever-evolving metropolis.

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  • Trip Point Pin1

    Chicago, IL

    Chicago, known as the Windy City, boasts an impressive skyline, the iconic Cloud Gate sculpture (also known as 'The Bean'), world-renowned museums like The Art Institute of Chicago, and a rich jazz and blues music scene. It's also famous for its deep-dish pizza and diverse culinary delights.
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  • Trip Point Pin2

    Evanston, IL

    Evanston offers a charming blend of big-city perks and small-town vibes with vibrant arts and culture, beautiful lakeside views, and the prestigious Northwestern University. It's a more relaxed alternative to the hustle of Chicago with plenty of unique shops and historic architecture.
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  • Trip Point Pin3

    Milwaukee, WI

    Milwaukee is famous for its breweries and the Harley-Davidson Museum, showcasing an important part of American motorcycle history. The city also has an attractive riverside setting, the Milwaukee Art Museum with its stunning architecture, and a strong German heritage that's celebrated in its festivals and food.
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  • Trip Point Pin4

    Sheboygan, WI

    Sheboygan is known as the 'Malibu of the Midwest' for its surfing community, thanks to the consistent wind patterns on Lake Michigan. It's also home to beautiful lakeside parks, art museums, and excellent golf courses, offering a mix of outdoor activities and cultural experiences.
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  • Trip Point Pin5

    Green Bay, WI

    Green Bay is synonymous with the NFL's Green Bay Packers and their historic Lambeau Field, which is a must-visit for sports fans. The city is also rich in history with the National Railroad Museum, and it offers beautiful natural scenery like the Green Bay Botanical Garden.
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  • Trip Point Pin6

    Mackinaw City, MI

    Mackinaw City is the gateway to the scenic Mackinac Island and acts as a hub for various outdoor activities, including hiking and fishing. It's known for the impressive Mackinac Bridge, historical sites like Colonial Michilimackinac, and is a great spot to enjoy fudge and explore unique local shops.
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  • Trip Point Pin7

    Traverse City, MI

    Traverse City is famous for its annual National Cherry Festival as it is located in one of the country's prime cherry-growing regions. It also boasts beautiful vineyards and wineries, stunning beaches along Lake Michigan, and is a gateway to the picturesque Sleeping Bear Dunes National Lakeshore.
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  • Trip Point Pin8

    Ludington, MI

    Ludington boasts miles of sandy shores along Lake Michigan, including the Ludington State Park, which is perfect for hiking, fishing, and camping. It's also home to the historic Big Sable Point Lighthouse and offers fantastic opportunities for water sports and sunset cruises.
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  • Trip Point Pin9

    Muskegon, MI

    Muskegon is a year-round adventure destination with its winter sports complex and summer beach activities. The city has a rich maritime history, which can be explored at the USS Silversides Submarine Museum, and offers cultural experiences through its art museum and historic sites.
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  • Trip Point Pin10

    Chicago, IL (return)

    Returning to Chicago allows you to explore any attractions you may have missed the first time or revisit your favorites. The city's vibrant neighborhoods, theater scene, diverse culinary options, and dynamic atmosphere offer new experiences with each visit.
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Local Events & Happenings


Music for Your Journey


    Tasty Picks


    Stay Recommendations

    • The Iron Horse Hotel

      Located in Milwaukee, this chic, industrial hotel is motorcycle-friendly and offers an authentic, upscale experience with a nod to the city's manufacturing legacy.
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    • The Drake Hotel

      This historic hotel in Chicago offers an opulent experience with timeless elegance and is famed for its unique architectural details and luxury accommodations.
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    • The American Club

      In Kohler, Wisconsin, this upscale resort provides a world-class hospitality experience, originally built for immigrant workers, and now offering luxury with a sense of history.
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    • Grand Hotel

      Situated on Mackinac Island, this hotel is notable for its grand porch, high tea service, and traditional decor; it's a step back in time with no cars allowed on the island.
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    • Hotel Metro

      An Art Deco-inspired boutique hotel in Milwaukee, where the sleek, vintage style is paired with modern comfort.
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    • The Cherry Tree Inn

      A charming bed and breakfast in Traverse City, known for its hospitality and cherry-themed décor, celebrating the region's cherry farming heritage.
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