Get your motor running and travel the historic Route 66 from Chicago to LA

Travel America’s most famous highway through the heart of cowboy country on the historic Route 66. First, learn the lyrics to the 1946 classic ‘Route 66’ (since recorded by over 50 different artists including Depeche Mode and Jerry Lee Lewis). Then, grab the biggest cowboy hat you can find. Finally, bring an appetite for all things America, where bigger is better. Follow the trail of the early settlers, migrants and travellers along the ‘Mother Street’ and watch the landscape change from the cityscape of Chicago, to the green fields of St Louis, to New Mexico’s arid desert and on to the flashing lights of Las Vegas. Take the road trip of a lifetime and get your kicks on Route 66.

Chicago, United States
Los Angeles, United States
United States
Physical rating
Cultural rating
Min 15
Group size
Min 1 Max 13
Carbon offset
0kg pp per trip


  • Driving Route 66 is one of the best ways to see small town America. Enjoy the true road trip experience with a local guide who knows the best places to stop, without the hassle of being in the driver's seat
  • Route 66 provides new adventures every day. Choose between 600 varieties of soda at Pops, take part in a steak challenge at The Big Texan Steak Ranch and visit Amarillo's modern version of Stonehenge at the famous Cadillac Ranch
  • Visit St Louis' Gateway Arch, famous not only for the views it provides over the city, but also for its role in the history of westward expansion in the USA
  • A visit to Acoma Pueblo with your guide provides access to the oldest continuously inhabited community in North America. Learn about Native American history, culture and traditions of Native Americans and their ancestors
  • Spend the night in a teepee at the unique Wigwam Motel in San Bernardino, before sock hopping back to the 50s with a movie at the nearby drive-in
  • After the bright lights of Las Vegas, your epic road trip ends in Los Angeles, City of Angels. Discover LA's iconic landmarks and secret gems with a local guide on an Urban Adventure day tour


Welcome to Chicago, USA. Your Route 66 adventure begins with an evening welcome meeting. Please look for a note in the hotel lobby or ask reception where it will take place. We'll be collecting insurance details and next of kin information at this meeting, so ensure you bring these details to provide to your leader. The rest of your night is free.

If you arrive early into the city, wander around to get your bearings and perhaps visit the Art Institute of Chicago or the Field Museum of Natural History. For spectacular views over the city, head to the Skydeck of the Willis Tower, the tallest building in North America.
Leave Chicago in the morning and drive south for over three hours to the first iconic stop on Route 66, Springfield. Pay a visit to the Lincoln Home National Historic Site, where Abraham Lincoln lived with his wife, Mary Todd Lincoln, until the year that he became president. Known as 'the birthplace of Route 66', Springfield is usually quite busy throughout the year with both international and domestic tourists. From here, cross from Illinois into Missouri and on to St. Louis for the night, which takes around one-and-a-half hours. Your evening is free to do as you wish.
After breakfast, use your morning to get to know the city before heading to the Gateway Arch. One of St. Louis' most significant landmarks, the arch scales nearly 200 metres into the air. You should also try and visit Ted Drewes Frozen Custard - an iconic Route 66 establishment since 1941. St. Louis is heavily associated with the music scene, particularly blues music. Perhaps spend the evening in one of the city's many music haunts.
Today hit the road again and drive towards Miami, Oklahoma. On the way visit the Meramec Caverns near Stanton, a system of limestone caverns spanning nearly eight kilometres (five miles) underground. See some of the rarest and largest cave formations in the world on a guided tour with a trained ranger. After your tour of the caverns, continue on to Miami. On arrival, perhaps take a tour of the historic Coleman Theatre. For something a bit more engineered, visit the Route 66 Vintage Iron Motorcycle Museum. Today's driving will take around 4-5 hours in total.
Today drive to Oklahoma City and stop at the small town of Arcadia along the way. Visit the Pops Soda Shop, a famous diner and gas station serving over 600 flavours of soda. On arrival into Oklahoma City, check in to the hotel and venture out to get a feel for the city. Use your free time to visit the National Cowboy and Western Heritage Museum, or take a walk through the sobering Oklahoma City National Memorial and Museum, which chronicles the 1995 Oklahoma City bombing. Today's total driving time is around three hours.
Today get back on the road towards Texas, stopping by the Oklahoma Route 66 Museum to learn about the iconic ideas, stories and myths behind the famous road. Then it's on to Amarillo, Texas, where you'll make your way to the Big Texan Steak Ranch for an optional 2 kg steak challenge. It's a near impossible task, so you might prefer to order something of more suitable proportions. Total driving time today will take between 6-7 hours.
After breakfast continue on your Route 66 adventure to the Cadillac Ranch. With ten classic cars buried nose-down in the dirt, this is a Texan version of Stonehenge. The owners of this iconic public art installation encourage graffiti, so pick up a mask and spray can and mark your legacy. Afterwards, venture into New Mexico and onto the city of Santa Fe, where you'll spend the night. Santa Fe is the oldest capital city in the US. Check out the pueblo architecture in the town plaza or see southwestern art and decor at the city's museums. In the evening, perhaps try some traditional southwestern cuisine for dinner. Today's total driving time is around seven hours.
Today leave the modern culture of Santa Fe behind and visit the 'Sky City' ruins in the ancient community of Acoma Pueblo. This fortified Indian reservation around 100 km west of Albuquerque consists of three villages. The local Indigenous community have lived in the area's sandstone mesa for over 800 years. Leave Acoma and head to the town of Gallup, where you'll spend the night. Your evening is then free to do as you wish. Today's driving will take a total of 3-4 hours.
Today is not a typical Route 66 stopover, as you veer off-track and head to the Grand Canyon. This national landmark is 433 kilometres (277 miles) long and 1.6 kilometres (one mile) deep, making it one of the largest canyon systems in the world. As you'll be staying close by, there will be plenty of time to explore the area. Stroll along the meandering South Rim Trail or hike down to Plateau Point. There's also the option of a scenic helicopter flight over the canyon (at your own expense). In the early evening, relax by the canyon's edge and take in the sunset. Today's total driving time will be around four hours.
Today’s drive will take around four hours. Leaving the Grand Canyon National Park, your first stop today will be the Arizonan town of Seligman. Seligman is famous for its Roadkill Cafe and the Historic Route 66 General Store. Continue onto the bright lights of Las Vegas. On arrival, the group will sit down for a buffet dinner together at one of the desert city's many casinos.
Today is free to explore Las Vegas. This may be the gambling capital of the world, but if betting your luck isn't your thing, there's plenty of other things to do inside and outside of the casinos. Perhaps board the High Roller ferris wheel or The Stratosphere tower to get amazing views of The Strip. Do some shopping or take a walk around the city's famous casinos; Caesar's Palace, the Venetian and the Bellagio are particularly elaborate. If you really want to see something different, poke your head into one of the countless wedding chapels. Las Vegas is a city built for entertainment, after all.
Leaving Las Vegas today, make the three-and-a-half hour drive to San Bernardino in California. Stop at Peggy Sue's diner en route for lunch. Built in 1954, this is the original roadside diner, and is kitted out with retro memorabilia and traditionally attired waiters. Tonight you'll stay at the Wigwam Motel, a village-style arrangement of 30-foot-tall tepees made from wood, concrete and stucco. Each individual wigwam is carefully equipped with traveller essentials, an outdoor barbecue grill and swimming pool. After dinner tonight, the group will head to the local drive-in movie theatre.
In the morning, drive the short distance to Los Angeles, ending your journey along Route 66 at the rustic amusement park of Santa Monica Pier. On arrival, perhaps take a ride on the park's historic carousel. This afternoon, take in the major sites of Los Angeles on an Urban Adventure day tour around the city with the group. Your evening is then free to do as you wish.
After breakfast, your Route 66 adventure comes to an end. There are no more activities planned for today and you're free to depart your accommodation at any time.
View trip notes to read full itinerary


3 breakfasts, 2 lunches, 1 dinner
Private vehicle
Hotel (12 nights), Motel (1 night)
Included activities
  • Lincoln Home National Historic Site
  • Gateway Arch
  • Meramec Caverns
  • POPS Soda Shop
  • Acoma Indian Reservation & Sky City Pueblo
  • Grand Canyon National Park
  • Las Vegas Buffet Dinner
  • Drive-In Movie
  • Los Angeles Urban Adventure


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Important notes

1. A single supplement is available on this trip.

Trip notes

Want an in-depth insight into this trip? Your trip notes provide a detailed itinerary, visa info, how to get to your hotel, what’s included - pretty much everything you need to know about this adventure and more.

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US Route 66 , June 2016

US Route 66 , June 2016