Day 1: Excitement builds as we set off for our adventure on Route 66, “The Mother Road.” Our first night will be in Springfield IL.

Day 2: This morning we continue north to Chicago, the starting point of “The Mother Road.” We will walk to the Historic Route 66 Begin Sign for photos and continue with a tour of Chicago. This evening dine at the famous Dell Rhea’s Chicken Basket. Overnight outside of Chicago. (B, D)

Day 3: Our first stop is at the Route 66 welcome center in Joliet IL. The Rialto Square Theatre is more than a venue—it's a breathtaking experience. Originally opened in 1926 as a vaudeville movie palace, this architectural gem blends historic grandeur with modern versatility, making it the perfect destination for unforgettable moments. We will start by enjoying a marvelous tour of the historic Rialto Square Theatre then return to the Rotunda for a delicious lunch buffet. And then end our experience with a mini-concert on the world renowned Barton Grande Theatre Pipe Organ. This afternoon we take as much of the original Route 66 as we can making stops along the way at Gemini Giant as well as other unique small town stops. Dinner will be at the Old Route 66 Family Restaurant before calling it a night. (B, L, D)

Day 4: Our day starts where Route 66 history dates back to the earliest days of the “Mother Road”. We visit Illinois Route 66 Hall of Fame & Museum, take a trolley tour seeing the unique collection of outdoor murals. We also learn more about the life of Bob Waldmire through his murals, famous VW minivan, and his extraordinary Road Yacht. Then continuing down the old Route 66 road as much as possible, we visit Route 66 Memory Lane and Deadman’s Curve. Then on to the American Giants Museum before our overnight in Springfield IL. (B)

Day 5: This morning we visit Ace Sign Museum devoted to the art of sign-making, including historic Route 66 signs. Lunch is at Route 66 Motorheads Bar, Grill, and Museum. We continue on to Litchfield Welcome Center on Route 66. By late afternoon we arrive in St Louis at the Gateway Arch for a ride to the top. We finish the day with a cruise on the Mississippi River. Overnight is west of St. Louis. (B, L, D)

Day 6: We start the day at Meramec Caverns. With over 50 billboards along the historic Route 66 highway, Meramec Caverns is a must-see roadside attraction. We explore the rumored hideout of outlaw Jesse James, walk the same paths used during the Civil War, and marvel at the Stage Curtain, a towering drapery formation. Cuba, Missouri has earned the nickname “Route 66 Mural City” thanks to its vibrant and creative approach to advertising its place along the historic highway. Rather than relying solely on traditional billboards or signage, Cuba has transformed its town into a living canvas that celebrates Americana, history, and roadside charm. Our overnight is in Springfield MO at the Best Western Route 66 Rail Haven. (B, L, D)

Day 7: A step on guide joins us on Springfield’s Route 66 attractions. Then we visit the Route 66 Car Museum exploring over 70 classic and celebrity cars while learning about the history and stories behind the vehicles, from brass era to sports cars. We continue to the Kansas portion of Route 66 stopping at Visitor Centers and other attractions like the Rainbow Historic Bridge. Nestled along historic Route 66, the Coleman Theatre is more than a venue—it's a living masterpiece. Built in 1929 by mining magnate George Coleman, this architectural gem boasts a Spanish Colonial Revival exterior and a breathtaking Louis XV-style interior that rivals the grandest theaters of Europe. Tonight, dinner is served on the stage. (B, D)

Day 8: You can’t do Route 66 without a picture stop at the Blue Whale! Next, discover the magic of America’s most iconic highway at the Heart of Route 66 Auto Museum, where vintage dreams come to life! Nestled in a historic National Guard armory, this one-of-a-kind destination showcases over 45 classic cars, rare automotive gems, and nostalgic Route 66 memorabilia that will transport you back in time. We continue making stops on Route 66 as we make our way to Oklahoma City for the night. (B)

Day 9: This morning finds us in Clinton, OK at the Oklahoma Route 66 Museum. This immersive museum invites you to relive the golden age of the Mother Road. We will continue our journey with stops at iconic attractions like the restored 1929 Gas Station, Transportation Museum, and more as we make our way to Amarillo TX. Tonight, we dine at The Big Texan Steak Ranch. (B, D)

Day 10: This morning we make it to the Midpoint Sign along Route 66. Time for our last pictures before continuing to home with our memories of the “Mother Road” (B)