Sample group itinerary

Route 66: Chicago to Santa Monica

11 days · Chicago to Los Angeles

This is a sample itinerary — an example of a trip we have built for groups, not a scheduled departure. We build every group trip around your travelers: the dates, length, pace, hotels and activities can all change.

Eleven days on the Mother Road, following the old alignment wherever possible: Chicago's architecture by river, Lincoln's Springfield, the Gateway Arch, Meramec Caverns, the Blue Whale, Cadillac Ranch, Petrified Forest, Seligman, the Wigwam Motel, and the end of the road at the Santa Monica Pier.

Day by day

Day 1
Arrive Chicago
Arrive in the Windy City, meet your tour director at the airport and transfer to your hotel in the heart of Chicago. After some time to relax and freshen up, take a short walk to where "The Mother Road" begins, the Historic Route 66 Begin sign, where you are sure to want a few pictures. Then join the group for a Chicago-style deep-dish pizza dinner, and finish the day with an evening architecture river cruise as the city makes its transition from day to night.
Dinner included
Day 2
Chicago to Springfield, Illinois
Start at Lou Mitchell's, dubbed the "first stop on the Mother Road," for a classic American diner breakfast. Then leave Chicago and begin your journey down the old road, driving Old Route 66 wherever possible. Stop for lunch on your own in Pontiac, with more Route 66 stops in Towanda and Normal. In Springfield, visit the Abraham Lincoln Presidential Library and Museum, which documents the life of the 16th president and the course of the Civil War. After checking in, enjoy dinner and Route 66 nostalgia at Motorheads Bar & Grill, with its own classic car museum.
Breakfast and dinner included
Day 3
St. Louis to Springfield, Missouri
Travel to St. Louis along Route 66 to tour the Gateway Arch, including a tram ride to the top. After lunch on your own, continue west to an iconic stop, Meramec Caverns, for a guided tour of its rare and beautiful mineral formations. Then continue to Cuba to see its 14 murals, and more roadside sights including the Giant Rocking Chair and Route 66 Motors in Rolla. Arrive in Springfield, Missouri, for dinner at a local restaurant.
Breakfast and dinner included
Day 4
Springfield to Tulsa
Depart Springfield with a Route 66 stop in Carthage, then cross into Kansas for a picture stop at Cars on the Route in Galena. Cross into Oklahoma and tour the historic Coleman Theatre in Miami, with lunch included. In the afternoon, stop at Ed Galloway's Totem Pole Park and the Blue Whale as you travel the Mother Road to Tulsa for a two-night stay. The evening is free to explore and have dinner on your own.
Breakfast and lunch included
Day 5
Tulsa to Oklahoma City
After a leisurely morning, continue along Route 66 to Chandler for the Route 66 Interpretive Center, a visual "drive" through Oklahoma on what John Steinbeck called the Mother Road. Visit the Arcadia Round Barn, then POPS, where more than 600 kinds of soda go with a classic drive-in lunch on your own. In Oklahoma City, tour the First Americans Museum, which shares the histories of the 39 First American Nations in Oklahoma today. Check into your hotel in Bricktown with the evening free.
Breakfast included
Day 6
Oklahoma City to Amarillo
This morning, visit the Oklahoma City National Memorial, which honors everyone affected by the bombing of April 19, 1995. Continue west to Clinton for lunch on your own and the Oklahoma Route 66 Museum, then on to Elk City and the National Route 66 Museum, with murals and scenes from all eight Route 66 states. Arrive in Amarillo and join the group for a true Texas experience at the Big Texan.
Breakfast and dinner included
Day 7
Amarillo to Albuquerque
Leaving Amarillo, a must-stop is Cadillac Ranch: ten Cadillacs, from a 1949 Club Sedan to a 1963 Sedan de Ville, half-buried nose-down in a Texas field with their tail fins held high. Cross into New Mexico, the Land of Enchantment, and enjoy the Route 66 nostalgia of Tucumcari, home of the Blue Swallow Motel and Tee Pee Curios. In Santa Rosa, drive Route 66 through town and stop for lunch on your own. The rest of the day is free in Old Town Albuquerque, with its narrow streets, century-old adobe houses, New Mexican eateries and artisan shops.
Breakfast included
Day 8
Albuquerque to Flagstaff
Travel west with a stop in Gallup at the El Rancho Hotel, lovingly preserved in its 1930s glory. Enter Arizona and arrive at Petrified Forest National Park for lunch on your own and sightseeing, with a scenic drive through the Painted Desert and Blue Mesa and a walk through the Crystal Forest. Then pass through another town full of Route 66 nostalgia and made famous in a song: Winslow, Arizona. Arrive in Flagstaff for dinner at a local restaurant.
Breakfast and dinner included
Day 9
Flagstaff to San Bernardino
West of Flagstaff lies Seligman, the "Birthplace of Historic Route 66," where barber Angel Delgadillo and his neighbors founded the Historic Route 66 Association of Arizona after the interstate bypassed the town. From here, drive the longest remaining stretch of the original road through Peach Springs and Hackberry to Kingman, with lunch on your own at Mr. D'z Route 66 Diner. Then cross the desert mountains to Needles and the Mojave Desert, with Route 66 picture stops on the way to Barstow and Elmer's Bottle Tree Ranch. Spend the night at the fun and historic Wigwam Motel, with dinner included at a local restaurant.
Breakfast, lunch and dinner included
Day 10
Hollywood and Santa Monica
Stop for breakfast at a local diner, then enjoy an open-air tour of Hollywood, West Hollywood and Beverly Hills: the Hollywood Sign, the Walk of Fame, the Sunset Strip, Rodeo Drive, the Chinese Theatre and celebrity homes. After lunch on your own at the Original Farmers Market, drive to the Santa Monica Pier and the western end of America's Main Street. Then celebrate the journey with a farewell dinner at a local restaurant — a fitting end to a nostalgic trip.
Breakfast and dinner included
Day 11
Journey home
After breakfast, transfer to Los Angeles Airport for your flight home.
Breakfast included