Touch down in Chicago and settle into the city before meeting your Travel Director and fellow travelers over dinner. It’s a chance to get to know each other and toast to the adventure to come.

Begin the day with an orientation tour of Chicago alongside your Travel Director, taking in landmarks like Cloud Gate, the Magnificent Mile and Navy Pier. Step aboard an optional Chicago River cruise and see the city’s skyline from a new perspective. Pass over 40 architectural landmarks as your Local Specialist shares the engineering and design stories that shaped Chicago into a global hub. After returning to the hotel, the rest of the day is yours, you could explore more of the city, visit a museum or simply relax before the journey continues.

Travel to Farmhaus Cider Co., where you’ll meet John and Megan Behrens for a Be My Guest experience. Sip exclusive small-batch ciders in the Cidergarten and enjoy a three-course Tuscan-style meal, learning how this fifth-generation farm became an award-winning cider house. Arrive in Grand Rapids, known for its thriving craft beer scene, riverfront trails and vibrant downtown. You’ll have the evening to explore as you choose. Visit one of the city’s breweries, take a stroll along the Grand River or unwind at your hotel before the journey continues.

Leave Grand Rapids behind and travel north to Charlevoix, a lakeside town with impressive harbor views. Take time to explore and stop for lunch before continuing to Mackinaw City. From here, take the ferry across the Straits of Mackinac to car-free Mackinac Island. Settle into island life with a horse-drawn carriage ride to the Grand Hotel, your Stays with Stories accommodation for tonight, famous for its sweeping porch, lakefront setting and more than a century of hospitality.

Set off around the island on a private horse-drawn carriage tour, a tradition dating back over a century. Stop to take in the views from Arch Rock, visit Fort Mackinac and pass landmarks that tell the island’s story. This afternoon enjoy lunch at the hotel, enjoying the elegant surroundings. Spend the rest of the day exploring the island as you like. Wander the shops, cycle along the shoreline or simply relax at the Grand Hotel.

Take the ferry back to Mackinaw City and continue south to Frankenmuth, known as "Little Bavaria”. With its Bavarian-style buildings, this town offers a taste of Germany in the heart of Michigan. Dive into Culture with pretzel rolling at the Bavarian Inn, learning the technique before enjoying the results of your work. The rest of the day is yours, perhaps stroll through the boutique-lined streets, stop by a German bakery or relax with a stein before settling in for the night.

Your day begins at the Tuskegee Airmen National Museum, a MAKE TRAVEL MATTER® Experience, where a docent-led tour explores the legacy of the first African American military aviators and their role in World War II. See aircraft they once flew and learn how their impact continues through youth training programs and scholarships. Next, get to know Detroit on an orientation tour, passing landmarks that reflect its industrial history, cultural influence and ongoing revitalization. In the afternoon you have the option to step inside the Guardian Building, a striking Art Deco skyscraper, for an exclusive tour. Gain access to hidden bank vaults, admire the intricate design and hear stories of its significance in the city's financial past.

Spend the day exploring the Henry Ford Museum of American Innovation, where exhibits celebrate the ideas and inventions that shaped modern life. See the bus where Rosa Parks refused to give up her seat, sparking the Montgomery Bus Boycott. Step inside a presidential limousine and learn about breakthroughs in automobiles, aviation and industry. In the evening, join your Travel Director and fellow travelers for a final dinner, sharing highlights from your journey and toasting to the memories you’ve made along the way.

After exploring Mackinac Island, the Great Lakes, and the rich history of the Midwest, it’s time to say goodbye to your Travel Director and fellow travelers before heading to the airport for your onward travels.