Day 1 – Welcome Dinner

Begin your journey on the legendary “Mother Road.” Travel to Chicago, where Route 66 begins, and enjoy a Welcome Dinner at a classic Route 66 restaurant. (D)

Day 2 – Chicago to Springfield

Start at the “Begin Route 66” sign and travel original stretches of the Mother Road. Visit restored gas stations, the Route 66 Hall of Fame, and the elegant Davis Mansion. In Springfield, explore Lincoln history or more Route 66 sites. Dinner on your own, with the option to join the group at the Cozy Dog Drive-In. (B)

Day 3 – Springfield to St. Louis

Visit quirky roadside icons including the world’s largest ketchup bottle and the Dixie Family Restaurant. Stop at Motorheads and the Litchfield Museum before arriving in St. Louis. Dinner includes a sweet stop at Ted Drewes Frozen Custard. (B, D)

Day 4 – St. Louis to Joplin

Head through the Ozarks, stopping at the Mule Trading Post, the giant rocking chair, and Meramec Caverns. Experience the historic 66 Drive-In Theater before settling in Joplin. (B, L)

Day 5 – Joplin to Oklahoma City

Step into nostalgia at Riverton Nelson Old Store, then visit Pops Soda Shop with its rainbow wall of sodas. Stop at the OKC Mustang Car Show before checking into your Bricktown hotel. Dinner included. (B, D)

Day 6 – Oklahoma to Amarillo

Tour the Route 66 Museum, visit the art-deco U Drop Inn Café, and see the Leaning Tower of Texas. End with a lively dinner at the Big Texan Steak Ranch. (B, D)

Day 7 – Amarillo to Albuquerque

Stop at Cadillac Ranch and the Glenrio ghost town before continuing to Santa Fe to explore Native American art and adobe architecture. Arrive in Albuquerque for dinner overlooking the Sandia Mountains. (B, D)

Day 8 – Great Sand Dunes National Park

Though Route 66 ends in Albuquerque, continue north to Colorado. Visit Great Sand Dunes National Park before reaching Lonetree, south of Denver, for a Farewell Dinner. (B, D)

Day 9 – Golden Spike Tower & Home

Stop at the Union Pacific Railyard and Golden Spike Tower to see the world’s largest rail yard. Return home with memories of the first half of your Route 66 adventure. Part Two continues to Los Angeles in 2026. (B)