Route 66 100th year Anniversary

September 8-19, 2026

12 days / 11 Nights

Day 1: We depart for a unique adventure on Route 66. Tonight, we arrive in Toledo, OH for an included welcome dinner. (D)

Day 2: This morning you will enjoy an included breakfast before driving by the official start of Route 66 in Chicago, IL. We will have lunch at Weber Grill Restaurant, where grilling is a lifestyle and synonymous with entertaining. Next we board the Wendella Cruises for a 90-minute narrated tour of Chicago Architecture. You will also experience 360 Chicago and TILT. Dinner will be on your own after you check into your hotel. (B, L)

Day 3: After breakfast, we will meet our tour guide for a tour of the “Windy City.” We will see some iconic sites like the Chicago “Bean” and Buckingham fountain. Lunch will be at the Berghoff Restaurant, the oldest continuously operated eatery on Route 66. Our next stop is Joliet Area Historical Museum where you can get a photo at their Route 66 diner scene. Dinner is also included today at the Route 66 Motorheads Bar and Grill, Museum and Entertainment Complex. Our day ends at the Illinois Route 66 State Fairground. (B, L,D)

Day 4: Start your day with a delicious breakfast at the hotel before we head to St. Louis, MO, enjoying photo opportunities along the way including the Old Chain of Rocks Bridge. Lunch will be on your own at City Foundry STL. Our next experience is the Gateway Arch, where the views are breathtaking. We visit the Route 66 State Park Visitors Center followed by Cuba, MO, known as the city of murals. We will make a stop at the George M. Reed Roadside Park which features Route 66 neon signs that have been restored. Dinner is included at Colton’s Steakhouse before we check into our hotel for the night. (B, D)

Day 5: After breakfast we make a quick stop at Buc-ee’s before heading to the History Museum on the Square. Learn the history of Route 66. Lunch is included at Cozy Dog Drive In – home of the “original” hotdog on a stick. Additional stops include Route 66 Car Museum, and the Bass Pro Shop Wonders of Wildlife Museum and Aquarium. Dinner is included at the Hemingway Blue Water Café. (B, L, D)

Day 6: Following breakfast at the hotel, we head to the Fantastic Caverns to experience America’s ride through cave. We will pause at Gary Gay Parita, a recreation of a 1930 Sinclair gas station. Lunch will be included at Granny Schaffers. A step-on guide will give us a tour of Joplin, MO before we head to Oklahoma. Oklahoma has the longest stretch of Route 66. On the way there is the photo stop at the Blue Whale of Catoosa, one of the most recognizable attractions on Route 66. Dinner is on your own after you check into your hotel. (B, L)

Day 7: Breakfast is at your hotel. We will spend the day in Tulsa, OK with a guided tour. Lunch will be on your own. Next we visit Route 66 Historical Villages an open-air museum. Travel along the original Route 66 to Stroud, OK, home of the famous Rock Café. We will continue to McJerry 66 Galleries, Jerry McClanahan is a premier expert on all things Route 66. Dinner is on your own after we arrive at the hotel. (B)

Day 8: Following breakfast we arrive at the Oklahoma State Capitol, the only capital in the world surrounded by working oil wells. Lunch will be on your own before we visit the Oklahoma City National Memorial. Next we arrive at the Skydance Pedestrian Bridge- part art, part bridge. Our next stop is the American Banjo Museum followed by a tour on the Bricktown Water Taxi. Dinner is included at Charleston’s Restaurant. The final stop of the evening is the Centennial Land Run Monument. (B, D)

Day 9: A good morning starts with breakfast at the hotel, especially before a morning of driving. We arrive at Brown’s Catfish for an included seafood buffet. We get back on the road and check into our hotel for the night. Dinner is included at Charlie Vergos’ Rendezvous Memphis, TN. After dinner explore the famous Beale Street nightlife on your own. (B, L, D)

Day 10: After an included breakfast, we get back on the road to make our way to Loretta Lynn’s Ranch. Take a tour and enjoy an included lunch. Next we will visit the Belle Mead Historic Site and Winery for a tour and wine tasting. Dinner will be at our hotel tonight. (B, L, D)

Day 11: We savor our breakfast and a hot cup of coffee before heading to the Ryman Auditorium in Nashville for a guided tour. We travel to Pigeon Forge for a stop at Alcatraz East Crime Museum. Dinner is included at Applewood Farmhouse Restaurant. We get back to our hotel for a restful night’s sleep. (B, D)

Day 12: One last breakfast before we hit the road for home, filled with pleasant memories of our Route 66 adventure. (B)

Price per person:

Single

Double

Price includes: Bus transportation, listed meals, all hotels, and attractions