Day 1 – Welcome to the Mother Road

Your Route 66 adventure begins as you fly into Chicago, the birthplace of the legendary Mother Road. After arriving, head to the iconic Navy Pier, where you'll have time to stroll along the waterfront, browse the shops, and soak in the energy of the Windy City. Next, stop for a group photo at the historic Begin Route 66 sign—the perfect way to kick off your journey. This evening, gather with your fellow travelers for a delicious welcome dinner before checking into your hotel and resting up for the adventures ahead. (D)

Day 2 – Route 66 Roadside Icons

Today, your journey down the legendary Mother Road truly begins as you travel toward Springfield, Illinois. Along the way, stop in Pontiac to explore the Route 66 Hall of Fame & Museum before continuing to Atlanta, Illinois, home of the quirky American Giants Museum and some of Route 66's most beloved roadside attractions. You'll also discover several other iconic stops that capture the nostalgia and charm of America's most famous highway. After checking into your hotel, enjoy dinner on your own at the legendary Cozy Dog Drive-In, birthplace of the famous Cozy Dog. Then, end the evening with the immersive Route 66 Experience at the Illinois State Fairgrounds, where the history and spirit of the Mother Road come to life. (B)

Day 3 – Lincoln's Legacy & Route 66 Classics

Begin your day by exploring the fascinating Abraham Lincoln Presidential Museum, then visit Lincoln's Home National Historic Site, where America's 16th president lived, before heading to the White House. Enjoy lunch on your own at the popular Motorheads Bar & Grill, a favorite stop for Route 66 travelers. This afternoon, continue to Litchfield to visit the Litchfield Museum and the nostalgic Sky View Drive-In, celebrating the golden age of the Mother Road. By evening, arrive in St. Louis and check into your hotel before gathering for a delicious group dinner at an iconic Route 66 restaurant. End the night with a sweet treat at the legendary Ted Drewes Frozen Custard, a St. Louis tradition since 1929. (B, D)

Day 4 – Quirky Route 66 Gems

Today is filled with some of Route 66's most memorable and offbeat attractions. Make a stop at the famous Uranus Fudge Factory before enjoying an included lunch at the nostalgic Route 66 Diner. This afternoon, tour the beautifully restored Boots Court Motel, one of the most iconic lodging stops along the Mother Road, then browse for unique souvenirs at the historic Old Riverton Store. This evening, check into your hotel and enjoy dinner on your own as you relax and reflect on another fun-filled day along Route 66. (B, L)

Day 5 – Oklahoma Route 66 Classics

Continue your journey along the Mother Road with a stop at the iconic Arcadia Round Barn, one of Route 66's most recognizable landmarks. Next, visit the colorful POPS 66 Soda Ranch, where hundreds of unique soda flavors and its towering soda bottle make for a fun and memorable stop. This afternoon, arrive in Oklahoma City and check into your hotel before gathering with your fellow travelers for an included dinner at the legendary Cattlemen's Steakhouse, an Oklahoma City institution since 1910. (B, D)

Day 6 – Across the Texas Panhandle

Today, continue following the legendary Mother Road with stops at some of Route 66's most iconic attractions. Explore the Oklahoma Route 66 Museum before discovering the fascinating Devil's Rope Museum, dedicated to the history of barbed wire and the American West. Cross into Texas to see the quirky Leaning Tower of Texas and the colorful Slug Bug Ranch, where vintage Volkswagen Beetles have become a one-of-a-kind roadside landmark. This evening, enjoy an included dinner at the world-famous Big Texan Steak Ranch before checking into your hotel for the night. (B, D)

Day 7 – Halfway Down the Mother Road

Today marks an exciting milestone as you officially reach the halfway point of Historic Route 66! Stop at the famous MidPoint Café in Adrian, Texas, where travelers have celebrated the halfway mark for generations. Continue your journey with a visit to the beautifully restored Blue Swallow Motel, one of Route 66's most treasured landmarks, and explore the fascinating Route 66 Auto Museum, home to an impressive collection of classic cars and memorabilia. This evening, arrive in Albuquerque, New Mexico, where you'll gather with your fellow travelers for a delicious group dinner before settling in for the night. (B, D)

Days 8 - 14:  Please see our brochure for full itinerary and details!