Our adventure begins in Chicago as we travel west to the Mississippi River. Enjoy a scenic lunch cruise aboard the Celebration Belle, explore the home of American Pickers in Le Claire, and discover the world of John Deere. We'll also visit a beloved old-fashioned ice cream parlor before enjoying dinner and settling into the historic Hotel Blackhawk in Davenport.

Start with a visit to the enormous Iowa 80 Truckstop and the nostalgic Wilton Candy Kitchen before arriving in the Amana Colonies. Enjoy a traditional German-inspired lunch, learn about the fascinating communal society that once flourished here, and explore the village's distinctive shops. The day concludes with a communal-style dinner and an overnight stay at the beautifully restored Hotel Millwright.

Journey through the Iowa countryside to Dutchman's Store, a Mennonite-run market in the village of Cantril known for its incredible variety of groceries, bulk foods and bargains. Continue to Eldon, where we'll visit a historic railroad depot and the farmhouse immortalized in Grant Wood's American Gothic. Our day ends in Pella, a picturesque community celebrating its Dutch roots with distinctive architecture, welcoming streets and traditional flavors.

Enjoy a leisurely morning exploring Pella's shops before heading to Winterset, birthplace of Hollywood legend John Wayne. Visit the museum dedicated to the Duke's remarkable career, then discover the picturesque covered bridges made famous by the novel and film The Bridges of Madison County. Spend the evening in Winterset, surrounded by the landscapes that inspired one of America's most beloved romantic stories.

Discover the beauty of the Iowa Arboretum & Gardens before heading to Boone for a day of railroad adventures. Enjoy a scenic lunch excursion aboard a heritage train, then experience Iowa's countryside from a different perspective with Rail Explorers' pedal-powered railcars. After dinner and some time to explore downtown Boone, an optional evening excursion offers a chance to see the spectacular High Trestle Trail Bridge.

Relive two unforgettable chapters of American music history. Near Clear Lake, visit the memorial to Buddy Holly, Ritchie Valens and the Big Bopper, then tour the legendary Surf Ballroom. Continue to Mason City, hometown of Meredith Willson and inspiration for The Music Man, to explore Music Man Square and the MacNider Art Museum. Tonight, stay at the historic Park Inn Hotel, the world's last remaining Frank Lloyd Wright-designed hotel.

Step into movie history at the famous Field of Dreams baseball diamond near Dyersville, where we'll tour the farmhouse and enjoy a special appearance by one of the Ghost Players. Travel through northeastern Iowa's scenic countryside before arriving in Dubuque, one of the oldest cities along the Mississippi River. Enjoy a memorable dinner and spend the night at the elegant Hotel Julien Dubuque.

Our final day takes us across the Mississippi to charming Galena, Illinois, where you'll have time to explore its beautifully preserved downtown or visit the home of President Ulysses S. Grant. After lunch, continue to Woodstock, another picturesque town with a Hollywood connection as a filming location for Groundhog Day. Enjoy a farewell dinner before returning to Chicago, bringing our Legendary Iowa adventure to a close.