Arrive in the city of Chicago, Illinois, situated on the southwestern shores of Lake Michigan, and make your way to your centrally located hotel. Once settled, you have the rest of the day to relax of explore the ‘Windy City’.

Chicago is rich in history and a musical soul, from the soaring architecture of the Loop and Millennium Park to the lively neighbourhoods of River North and the West Loop.

Spend time along the Chicago Riverwalk, see famous landmarks such as the Willis Tower and Cloud Gate, or head out in the evening to one of the city’s jazz and blues venues, including those found around South Side neighbourhoods such as Bronzeville.

The Drake Chicago or similar

Step outside today and experience mile after magnificent mile of the ‘Windy City’. Stand on the corner of Michigan and Adams, marked as the starting point of Historic Route 66. Enjoy coffee and a big breakfast at Lou Mitchell’s, a Chicago institution since 1923 and a must for Route 66 travellers. Stroll the lakefront, peruse the shops, bike the parks, grab a Chicago Dog, or explore the city’s incredible sights and architectural treasures including Willis Tower, one of the tallest buildings in North America.

Optional Experiences:

• Chicago Helicopter Tour – Fly above the city skyline by day or night, learning about Chicago’s history and landmarks from your experienced pilot.
• Inside Chicago Grand Tour – Visit the city’s top landmarks and attractions on this grand tour that takes you with an expert guide, to all the best spots.

Speak to your travel expert about booking one of these optional experiences, or ask for a Chicago CityPASS, offering VIP admission tickets to must-see tourist attractions in Chicago including the Shedd Aquarium, Skydeck Chicago, and The Field Museum.

The Drake Chicago or similar

This morning, pick up your rental car and get ready for an unforgettable journey into the then and now of America along the Historic Route 66. This legendary old road passes through a variety of pure Americana landscapes and takes in some of the country’s biggest, oldest, and most peculiar sites along the way.

Leaving Chicago behind, follow the historic route south-west across Illinois, towards St. Louis, Missouri, cruising through endless cornfields and flat prairies. En route, don’t miss Wilmington’s most photographed ‘citizen’, the larger-than-life green Gemini Giant, and Atlanta’s Bunyan Giant, a 19 foot statue of Paul Bunyan holding a giant hot dog.

Continue south to Springfield, Illinois, the state capital, and stop at the Cosy Dog DriveIn, a long-standing Route 66 institution known for its battered hot dogs on sticks, and explore the legacy of Abraham Lincoln with a visit to the Lincoln Home National Historic Site.

From Springfield, continue south through Illinois before crossing the Mississippi River into Missouri and arriving in St. Louis, the largest city along Route 66. Here you can follow in the footsteps of legendary explorers by visiting the historic sites found throughout the city, including the Gateway Arch, the nation’s tallest monument.

Chicago > St. Louis | 300 miles

St. Louis Union Station or similar

Continue through the Ozark Highlands to Springfield, Missouri, recognised as the birthplace of Route 66.

En route, stop at Meramec Caverns, an extensive set of natural limestone caves whose formations and colours are as unique as they are beautiful. Adding to the pleasure of exploring the caves is learning the local legend of Jesse James and his gang, who were believed to have used them as a hideout, escaping via the underground river through a ‘back door’.

Once you arrive in Springfield, check into your hotel and leave time to explore the city. Known as the ‘Queen City of the Ozarks,’ Springfield, Missouri is the third-largest city state home to the Wonders of Wildlife National Museum & Aquarium, Dickerson Park Zoo, and Wilson’s Creek National Battlefield. The city also features one of the many Route 66 Car Museums, showcasing a collection of classic cars and film replicas.

St. Louis > Springfield | 210 miles

Best Western Route 66 Rail Haven or similar

This morning, leave Springfield and continue west through Missouri towards Joplin, before crossing the state line into Kansas near Galena. Cut through the southeastern corner of Kansas on your way to Oklahoma City, passing through Galena, Riverton, and Baxter Springs then crossing into Oklahoma; a state paved with more drivable miles of Route 66 than any other.

En route to Oklahoma City, you can still follow sections of early Route 66 alignment that recall the road’s importance to travellers and Dust Bowl migrants heading west during the 1930s.

Stop to view the beloved 20 foot tall cement Blue Whale in Catoosa, one of Oklahoma’s best-known Route 66 roadside landmarks, before continuing into Tulsa. Here, visit the Cyrus Avery Route 66 Memorial Bridge, honouring the ‘Father of Route 66’s’ and his role in routing the highway through the city.

Continue west to Oklahoma City, the state capital, home to old Route 66 motels, gas stations, and numerous vintage buildings, where you can check into your hotel with time to see the sights. Whilst here, admire western artworks at the National Cowboy & Western Heritage Museum or explore the historic working livestock exchange at the Stockyards City.

Springfield > Oklahoma City | 310 miles

Hampton Inn & Suites Oklahoma City Bricktown or similar

Leave Oklahoma City behind and continue west along Route 66 towards Amarillo, stopping in Clinton, Oklahoma on the way. Here you’ll find one of America’s Route 66 Museums, showcasing classic vehicles and memorabilia that trace more than six decades of history.

After admiring the exhibits, continue your journey across the state line into the wide, open landscapes of the Texas Panhandle. This area of Texas was once the buffalo-rich grasslands of the Great Plains, inhabited by bands of Kiowa and Comanche Indians. In Shamrock, stop to see the distinctive Art Deco Tower Station and U-Drop Inn Café, one of the most recognisable buildings on this stretch of Route 66. Further west, McLean is home to a restored Phillips 66 service station, while Groom is known for its famously leaning water tower and enormous roadside cross.

Arrive in Amarillo, the largest Texas city on Route 66. Once settled, be sure to stop at Big Texas Steak Ranch where you can attempt their 72 oz. steak challenge.

Oklahoma City > Amarillo | 260 miles

Hampton Inn & Suites Oklahoma City Bricktown or similar

Before leaving Amarillo be sure to visit Cadillac Ranch. This unique display of art features a row of ten colourfully painted Cadillac cars buried grille-first in the Texas Panhandle.

Continue along Route 66 to Adrian, recognised as the halfway point between Chicago and Los Angeles. Here, stop at the MidPoint Café, famous for its ‘ugly crust’ pies, before hitting the road again and following the historic highway across the Texas state line to New Mexico, Follow the ‘Mother Road’ towards Albuquerque for a great taste of the ‘Land of Enchantment.’

Amarillo > Albuquerque | 270 miles

Best Western Plus Rio Grande Inn or similar

The state’s largest city, Albuquerque spreads north and south along the banks of the Rio Grande. Spend the day exploring Downtown Albuquerque’s Central Avenue, a treasure trove of Route 66 landmarks.

Historic Old Town offers a taste of New Mexico’s Spanish colonial past while the Indian Pueblo Cultural Centre, owned by the state’s 19 different Pueblo communities, traces the history of the region’s Native American cultures.

Best Western Plus Rio Grande Inn or similar

Today, get a true sense of the Old Route 66 as you detour to New Mexico’s state capital, Santa Fe.

Founded on the ruins of an abandoned Indian village and steeped in history, Santa Fe is the oldest capital in the U.S., and although it lost its place on Route 66 in 1938, it remains one of the most picturesque cities in the state. At one time this was the end of the old Santa Fe Trail, the earliest trade route linking the American frontier back east with the far west.

Plan to visit one of Santa Fe’s famous art galleries, art markets, or museums full of traditional and contemporary art, including works by their own Georgia O’Keeffe, or shop for authentic creations you just won’t find anywhere else.

Albuquerque > Santa Fe | 116 miles

Best Western Plus Inn of Santa Fe or similar

This morning, the state of Arizona welcomes Route 66 travellers with an overwhelming display of trading posts. View huge concrete tepees that stand at the foot of brilliant red-rock mesas en route to Petrified Forest National Park, the only national park site in the National Park System containing a section of Historic Route 66. Here you will come face-to-face with over 13,000 years of human history and one of the world’s largest and most colourful assemblies of petrified wood, historic structures and archaeological sites. Catch a sunset over the Painted Desert from the park’s Kachina Point before heading to Holbrook.

Once in Holbrook, stop at the Wigwam Motel whose concrete teepees, featuring modern conveniences, have welcomed guests since 1950. You could also explore Bucket of Blood Street in the old downtown district or visit the Navajo County Historic Courthouse and Museum for a glimpse into Holbrook’s Route 66 and Wild West past.

Santa Fe > Holbrook | 260 miles

Best Western Arizonian Inn or similar

Continue to Meteor City, a true vintage trading post whose distinctive dome can be seen for miles along this stretch of Route 66. Pass through Flagstaff before arriving in Williams, your base for exploring Grand Canyon National Park.

Spend the day discovering the distinct South Rim of the Canyon. Stop at one of the numerous overlooks, walk part of the Rim Trail or along the historic Hermit Road. Stop at one of the South Rim’s best-known viewpoints, such as Mather Point or Hopi Point, or climb to the top of the Desert View for panoramic views that extend over 100 miles on clear days.

Holbrook > Grand Canyon | 180 miles

Grand Canyon Railway Hotel or similar

Leave the town of Williams and the Grand Canyon behind as you make your way to Seligman, the first stop heading west on the longest uninterrupted stretch of Route 66. Once here, be sure to grab yourself a souvenir from Angel & Vilma Delgadillo’s Original Route 66 Gift Shop before grabbing a treat from Delgadillo’s Snow Cap Drive-In.

Continue through Kingman whose old Route 66 cafés and motels still flourish, to one of Arizona’s hidden treasures, the Hoover Dam.

Hoover Dam straddles the mighty Colorado River, which forms the border between Nevada and Arizona and brings much-needed water and power to the Southwest.

Later, continue to Nevada, for two nights in Las Vegas, a city that needs no introduction.

Williams > Las Vegas | 300 miles

Planet Hollywood & Casino or similar

Enjoy a full day Las Vegas style. Walk the famous Strip, passing landmark resorts such as the Bellagio, Caesars Palace and The Venetian, or stop to watch the Fountains of Bellagio. Place a bet in one of the city’s casinos, browse the Forum Shops at Caesars Palace, or dine at one of the many restaurants along Las Vegas Boulevard. For a different view of the city, ride the High Roller observation wheel at The LINQ, or take on the Big Apple Coaster at New York-New York. Later, head downtown to Fremont Street for an evening of live entertainment, or simply head back to your hotel and unwind. The list goes on.

With so much to do, 24 hours in a day hardly seems like enough. Speak to your travel expert about extending your stay an extra day to give you more time to explore.

Optional experiences: 

• Las Vegas Helicopter Flight – fly above the bright lights and neon skyline taking in the iconic sights of the Las Vegas Strip
• Area 51 tour – Take a trip from Las Vegas, to the world’s most top secret military facility, and explore remote areas known for UFO sightings

Planet Hollywood & Casino or similar

This morning, leave Las Vegas and travel south-west through the Mojave Desert, crossing the Nevada–California state line and travelling through the desert towards Calico Ghost Town, California’s authentic silver mining town and one of the few original mining camps of the Old West.

Rejoin Route 66 in Barstow where a collection of historic photographs and artefacts related to Route 66 and the Mojave Desert communities are on display at the Route 66 Mother Road Museum.

Continue through Pasadena, Los Angeles, West Hollywood, and Beverly Hills to Santa Monica for a true Hollywood ending to your cross-country journey. Park and venture the last few blocks on foot to view the ‘End of the Trail’ sign on Santa Monica’s Pier. This sign officially marks the western end of Historic Route 66.

Las Vegas > Los Angeles | 290 miles

Hyatt Centric Delfina, Santa Monica or similar

Today, spend some time at the beach; with 3.5 miles of Southern California beaches and over 300 days of sunshine, Santa Monica Beach is a welcome retreat with a range of activities on offer.

Swimming, surfing, volleyball, skating and biking are among the favourite beach-side past times of this area. Or, you can choose to visit the glitz and glamour of Hollywood and shop on the famous Rodeo Drive, where luxury retail commands the street.

Optional experiences:

• Movie Stars Home Tour – leave your car at the hotel and let somebody else take the wheel today with this Los Angeles sightseeing tour that takes you past Movie Stars’ homes and the most popular beaches in California
• Universal Studios Hollywood – Spend the day at Universal Studios Hollywood, with rides, shows, a working movie studio, and lively shops and restaurants at CityWalk
• Disneyland Los Angeles – speak to to your travel expert about extending your stay in Los Angeles and make the most of a two day theme park pass to Disneyland, California

Hyatt Centric Delfina, Santa Monica or similar

Leaving Los Angeles today, set your sights on the beautiful natural landscape of Sequoia National Park, located in the southern Sierra Nevada mountain range. There’s something magical about being surrounded by groves of the world’s largest living things and that is exactly what you will experience today.

Sequoia National Park is a wonderland covered by ancient forests, soaring domes, granite canyons and at the heart of the park, in the shade of towering sequoias and redwood groves, the Giant Forest is home to half of the Earth’s largest and longest-living trees.

Los Angeles > Sequoia National Park | 226 miles

Wuksachi Lodge or similar

After waking to sights and sounds of Sequoia National Park, it’s time to leave one National Park in the direction of another. Today you are heading to the striking beauty of Yosemite National Park, also set across the Sierra Nevada mountain range.

You have a full day here inside Yosemite National Park to explore the natural wonders that surround you. Gaze upon the parks iconic sequoia trees, granite cliffs of El Capitan and Half Dome and the iconic vista of towering Bridalveil Fall from Tunnel View.

Sequoia National Park > Yosemite National Park | 159 miles

Tenaya Lodge or similar

After a final explore of Yosemite’s magnificent landscape this morning, make your way out of Yosemite and head towards the ‘City by the Bay’, San Francisco. On arrival, great attractions like the Golden Gate Bridge, Alcatraz Island and Fisherman’s Wharf await you.

The city is nice and compact so easily travelled on foot and by cable car, so we recommend you drop off your car at the depot today- parking charges here can be quite costly. Jump aboard the famous cable cars to make your way around the city’s many attractions.

The one place you won’t be able to get to on a cable car is Alcatraz Island! Sitting in the middle of San Francisco Bay, through the years, this island has served as a lighthouse, a military fortification, and finally as a federal prison. This evening make the most of the city’s vibrant nightlife and dine in one of San Francisco’s many distinctive neighbourhoods, from Chinatown to the very Italian flavoured North Beach.

Yosemite National Park > San Francisco | 196 miles

Hotel Whitcomb or similar

Bid farewell the ‘City by the Bay’ and head to the airport for your flight to the UK, or choose to extend your stay in San Francisco to discover more of this wonderful city.