Chicago to Springfield, Illinois (3 hours 15 minutes / 326 km)

Start today with breakfast at Lou Mitchell’s, a Chicago institution which has claimed to be “serving the world’s finest coffee” since 1923. There is some dispute about where Route 66 begins in Chicago, but a good place to start is the Route 66 sign on Adams Street, just west of its intersection with Michigan Avenue. The instantly recognisable Route 66 insignia hangs above a sign reading “BEGIN,” making this a perfect place to take your first trip selfie.

A great first stop is Joliet, Illinois, where you can explore the Route 66 Museum to get to know the “Muffler Men,” giant fibreglass statues used along the Route in the 1960s to advertise auto repair shops, diners and other roadside attractions. See your first Muffler Man in Wilmington, the 9-meter Gemini Giant promoting the Launching Pad Drive-In Restaurant, then head to Dwight for a stop at Ambler’s Texaco Gas Station, once the oldest continually operated gas station on the route. As you pass through Pontiac, don’t miss its collection of murals of President Abraham Lincoln. Be sure to visit Pontiac’s Route 66 Hall of Fame and Museum, with its collection of vintage ads, signs and memorabilia, before arriving at tonight’s destination, Springfield.

Overnight: Springfield, Illinois

Springfield, Illinois to St. Louis, Missouri (1 hour 25 minutes / 155 km)

Before leaving Springfield today, visit the Oak Ridge Cemetery to see the Lincoln Tomb – the final resting place of President Lincoln. The 35-meter monument that marks his gravesite is decorated by four ornate sculptures that honour Civil War servicemen. Next, head to Litchfield for a quick stop at the Litchfield Museum & Route 66 Welcome Centre before lunch at the Ariston Café. Open since 1935, it is among Route 66’s oldest restaurants.

After lunch, make your way to St. Louis, Missouri, crossing the mighty Mississippi River on the New Chain of Rocks Bridge. Be sure to stop to explore the now pedestrianised old Chain of Rocks Bridge to enjoy beautiful greenery along the river. The eye-catching Gateway Arch National Park is a perfect first stop upon arriving in St. Louis. Take a 190-meter tram ride to the top of the tallest monument in the United States and be awed by breathtaking views. Explore the Museum at the Gateway Arch to learn about the history of the USA and maybe even take a riverboat cruise down the Mississippi. For dinner, explore the St. Louis restaurant scene. Famous for its ribs, the city has plenty of excellent barbecue spots.

Overnight: St. Louis, Missouri

Oklahoma City, Oklahoma to Amarillo, Texas (4 hours / 256 km)

Depart Oklahoma City, and cross the steel truss bridge over Lake Overholser as you leave town. Continuing along Route 66, stop in Clinton‘s Route 66 Museum to experience the story of the Mother Road as you listen to the big band music of the era, sit in a booth at a 1950s diner and learn about life on
the road through images and sounds. As you cross the state line into Texas, stop at the gorgeous Tower Station and U-Drop Inn Café. This art deco edifice was once a popular gas station and café among Route 66 travellers. Today, it has been fully restored and houses a museum and gift shop.

Make a quick photo stop in Groom, at the whimsical Leaning Tower of Texas, an unconventional water tower built to look like it will come crashing down at any moment. Tonight, in Amarillo, visit The Big Texan Steak Ranch, famous for its quirky architecture and its flame-grilled steaks. If you have a big appetite, take on the 72oz Steak Challenge.

Overnight: Amarillo, Texas

Amarillo, Texas to Tucumcari, New Mexico (1 hour 45 minutes / 181 km)

A short drive west of Amarillo is the famous Cadillac Ranch, a striking installation made up of ten graffiti-covered Cadillacs buried halfway in the dirt in the Texas desert. This psychedelic ode to cars is an iconic photo op. A short distance west, celebrate your arrival halfway down Route 66 at the Midpoint Café in Adrian. After lunch, travel west to the historic ghost town of Glenrio. The Glenrio Historic District straddles the border of Texas and New Mexico, and locals
maintain that it was a filming location for the 1940 movie “The Grapes of Wrath.” You can still see the old Route 66 roadbed among the many now-unused historic buildings. Enjoy dinner tonight at Del’s Restaurant in Tucumcari, New Mexico; it’s easy to find due to the giant cow outside. With its neon signs, kitschy Americana architecture and locally owned motels, Tucumcari is home to a cornucopia of photo ops showcasing what Route 66 is all about. Take time to explore historic landmarks this evening, being sure to visit the Blue Swallow Motel.

Overnight: Tucumcari, New Mexico

Tucumcari to Albuquerque, New Mexico (2 hours 40 minutes / 283 km)

Before you leave town today, stop at the Tee Pee Curios gift shop, marked by the colourful concrete tepee outside. Stop for breakfast at retro diner Kix on 66; be sure to try the Kingman breakfast platter and the giant cinnamon rolls. Heading west, stop in the historic town of Santa Rosa to take a dip in the famous Blue Hole. Sightsee in the downtown plaza dominated by the stunning Guadalupe County Courthouse. Take the original Route 66 out of town, heading northwest to reach downtown Santa Fe.

Explore the Cathedral Basilica of St. Francis of Assisi and the luxurious La Fonda on the Plaza hotel, then enjoy lunch at La Plazuela in the hotel’s courtyard Departing Santa Fe en route to Albuquerque was once one of the most challenging parts of the journey, as the road descended 150 meters in just three kilometers thanks to 26 incredibly steep switchbacks. Start your Albuquerque experience with a relaxed dinner at the 66 Diner, housed in an old Phillips gas station. Try the Green Chile Cheeseburger, making sure to save room for a slice of house-made pie.

Overnight: Albuquerque, New Mexico

This morning, tour the Old Town and Downtown areas of Albuquerque along the stretch of Old Route 66 now known as Central Avenue. Must-sees include the KiMo Theater, a marvel of Pueblo Dec architecture, and the San Felipe de Neri Church, one of the oldest surviving buildings in the city. Stop for lunch at the Dog House Drive In, which television buffs may recognise from “Breaking Bad” and “Better Call Saul.” After over 50 years, this restaurant remains much the same, serving hot dogs, hamburgers and milkshakes from a modest brick shack. The Dog House bears one of the most recognisable neon signs along the route, delighting visitors with its depiction of an elongated dachshund wagging its tail and chewing on a string of sausages.

After lunch, visit the Historic Nob Hill neighbourhood to explore Central Avenue, with its glowing neon lights and signs marking the location of Old Route 66. This area is well-known for its colourful nightlife and diverse restaurants; if you like Mexican cuisine, try the whimsical Range Café.

Accommodation: Albuquerque, New Mexico

Albuquerque, New Mexico to Holbrook, Arizona (3 hours 20 minutes / 375 km)

Head west again today and make your first stop in the tiny village of San Fidel to browse the Acoma Curio Shop. Famous for its adobe walls, mining style façade and tin roof, this little abandoned building is one of the most popular stops on Route 66.

Continue to Thoreau, another small village along Route 66, defined by its Navajo roots and home to a local trading centre for turquoise and silver jewellery and artisan rugs. The old Roy T. Hermans’ Garage and Service Station is a supreme selfie stop; while it’s no longer serving gas, the Hermans still run a repair garage out of this building.

Roll into Arizona and make your final stop today at one of Route 66’s natural wonders, Petrified Forest National Park. Explore its almost otherworldly landscape along its 45-kilometre main road, which passes through the Crystal Forest Trail, an area with giant logs that have petrified to practically solid quartz, and the stunning Painted Desert, so named for its array of colours. Tonight, stay in Holbrook at the iconic Wigwam Village Motel #6 and get a good night’s sleep in an oversized tepee.

Overnight: Holbrook, Arizona

Holbrook to Flagstaff, Arizona (1 hour 50 minutes / 168 km)

Depart Holbrook and enjoy a late breakfast in nearby Winslow at La Posada Hotel in the famous Turquoise Room. Opened in 1930 as one of the most luxurious hotels in the Southwest, this Arizona gem was restored to its former glory in the 1990s and is still one of the most popular stops along Route 66. The town of Winslow is full of treasures, both historic and modern. Visit the Standin’ on the Corner Park on the corner of Kinsley and East 2nd Street, established to commemorate the USA band The Eagles’ first hit single, “Take it Easy,” which mentions Winslow by name. The park brings the
song’s lyrics to life with a statue of a guitar-bearing singer and a mural of “a girl” sitting “in a flatbed Ford” truck.

Just outside of Winslow, stop to view Meteor Crater, where a meteorite fell to Earth some 50,000 years ago. Then make your way toward Flagstaff, being sure to stop for lunch at Miz Zip’s, a retro Route 66 institution serving up burgers and pies. After lunch, view the block-long mural at South San Francisco Street, or, if you want to explore more, take the self-guided tour from the Visitor Centre.  This afternoon, take the 90-minute drive to Grand
Canyon National Park to admire the unforgettable beauty of the South Rim. Watch as the sun sets over the red rocks of the Grand Canyon for a truly awe-inspiring experience. Return to Flagstaff to see many iconic neon signs still lit, including the exciting moving wagon and horses that decorate the Western Hills Motel.

Overnight: Flagstaff, Arizona

Flagstaff, Arizona to Las Vegas, Nevada (4 hours / 405 km)

Take a short drive from Flagstaff to arrive in Williams. Drive down Main Street to view retro-chic signs, like the red car atop Cruiser’s Route 66 Café. The next stop is Seligman, another small Route 66 town full of colourful vintage gas stations, cafés and stores, all restored to their original glory. Stop at Delgadillo’s Snow Cap Drive-In, now a Guinness World Record holder for the “Largest Display of Milkshake Varieties,” for a sweet treat. One of the most important stops along the route is Kingman, where the Arizona Route 66 Museum traces the history of the Mother Road. Cross the street to enjoy a plate of barbeque ribs at Mr. D’z Route 66 Diner.

A short drive north through stunning Sitgreaves Pass is Oatman, an old mining town almost frozen in time, where the sidewalks are made of wood and wild burros roam the streets. Take a detour from Route 66 today and head north to Las Vegas, often referred to as the Entertainment Capital of
the World.

Overnight: Las Vegas, Nevada

Las Vegas, Nevada, has something for everyone. If you want to discover the origins of Las Vegas, then head downtown and visit the Mob Museum to explore the history of organised crime in the USA. Take time for lunch at Atomic Liquors, whose roof was once a viewing spot to watch the atomic explosions in the Nevada desert. Check out The Neon Museum Las Vegas, where iconic signs from past hotels have been brought back to life. To close out your day, visit the Las Vegas Strip to take in the neon lights and unforgettable nightlife that has made this exciting city world-famous.

Accommodation: Las Vegas, Nevada

Las Vegas, Nevada to Santa Monica, California 5 hours / 471km

Departing Las Vegas today, head south into California. Just across the state line, pass through the Joshua Tree Forest near Cima before rejoining Route 66 in Amboy. Stop at Roy’s Motel & Café to snap photos of its iconic neon sign and the Route 66 insignia on the highway. One hour west, visit Barstow and The Route 66 “Mother Road” Museum housed in the historic Casa del Desierto, where you’ll admire artifacts and images of the old road. Heading towards the Pacific Coast, Cajon Boulevard offers stunning mountain views of Cajon Pass as it joins up with Old Route 66. Continue to Downtown San Bernardino, where the First Original McDonald’s Museum offers a slice of Americana legend, as does the Route 66 map painted on the side of City Hall. The Wigwam Motel just outside town is a fun photo stop.

Take Foothill Boulevard down the path of Old Route 66 to reach Pasadena, where you’ll find the only remaining historical mile marker on Colorado Boulevard. Next, cross the Colorado Street Bridge, which was the world’s highest cement bridge when completed in 1913. Head through Downtown Los Angeles and make a stop at Grand Central Market for lunch before joining Sunset Boulevard, where you’ll see historic buildings and spectacular views of Los Angeles.

Follow Santa Monica Boulevard through West Hollywood to Beverly Hills and take a selfie at the Beverly Hills sign. Arrive in Santa Monica, stopping at the corner of Ocean and Santa Monica Boulevard before heading to the Santa Monica Pier. There, you’ll find a plaque dedicated to Will Rogers, the renowned comedian and actor who inspired people to drive Route 66. Your journey comes to an end as you step onto the pier, where a sign marks the official end of the Mother Road.

Tour Ends: Santa Monica, California