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Route 66 Holidays

Driving down Route 66 with the wind in your hair is a dream that can now become a reality, incorporating some of America's must-see cities on the way, this is a trip that cannot be missed!

To create your ultimate American fly drive, fill out an enquiry form and our experienced advisors will help you create the holiday of a lifetime.


Begin this road trip in The Windy City with a big breakfast and coffee at Lou Mitchell’s, one of the most famous diners in America. Chicago is also home to the Willis Tower, North America’s tallest building so be sure to take time out for that. Visit the gorgeous Millenium Park, take in some history lessons at the Field Museum or maybe catch some of the city’s famous improvisational comedy.

Walk down the Magnificent Mile will treat you to some spectacular views of the amazing architecture the city has to offer including the Chicago Water Tower.The University of Chicago Oriental Institute has a vast collection of Near Eastern and ancient Egyptian archaeological artefacts.

With the Adler Planetarium & Astronomy Museum, the Field Museum of Natural History and the Shedd Aquarium, you won’t run out of things to see and do. Classics like the Chicago Dog and a Maxwell Street Polish will give you the energy to take on your first spell on the road too.

St. Louis

From Illinois to Missouri as St. Louis will be the next stop. The world’s largest mosaic installation is housed in the Cathedral Basilica of St. Louis and well worth a visit. The city has a strong legacy of rock and roll, jazz, blues and ragtime, with legend Chuck Berry being a native of the area and Miles Davis making the rounds of jazz clubs in the area during his early days.

It is definitely a good plan to catch a musical show in one the local clubs. The Jewel Box is an intriguing art deco-designed greenhouse in Forest Park, hosting some gorgeous displays, perfect for a relaxing stroll. Be sure to grab some toasted ravioli, a St. Paul Sandwich or some gooey butter cake before you head on your way.

Springfield, MO

With a Springfield either side of St. Louis, it’s the Southernmost that will host you for a night. Widely recognised as the birthplace of Route 66 back in 1926, Springfield is situated in the heart of Ozark mountain region.

Be sure to visit the vast Meramec Caverns on route to Springfield, they have existed for over 400 million years, forming gradually through limestone deposits. With a history of interesting stories, these caverns are a great change of pace to visit.

Oklahoma City

Onto Oklahoma City next, but be sure to catch the Blue Whale of Catoosa structure on the way. The Museum of Osteology is the only one of its kind in the USA while the National Cowboy & Western Heritage Museum is very fitting. The Overholser Mansion, Centennial Land Run Monument and Oklahoma City National Memorial & Museum provide further historical and significant landmarks worth spending time at.


Stop off at the Route 66 Museum in Clinton for over six decade’s worth of history on the route. Then on to Amarillo, the largest city in the Texas panhandle. The Tri-State Fair & Rodeo every third week in September is a popular attraction whilst the American Quarter Horse Heritage Centre & Museum is very informative.

For the particularly plucky, or just plain hungry, the Big Texas Steak House offers a monumental challenge: a 72oz steak that is free for anyone who finishes within the hour… Good luck! If you need a quick time out from driving - or to undo the belt buckle after that! - Cadillac Ranch will offer you ten minutes of creative fun and a novel stop-off to enjoy a little break.


The Midpoint Café in Adrian is a great place to stop for a bite, to signify your progress and try some Ugly Crust Pies. Nothing ugly about the taste, that’s a promise. Once reaching Albuquerque, fans of The Simpsons may want to see what could have been with the baseball minor-league team the Albuquerque Isotopes, named as so because of an episode on the show.

Spread along the Rio Grande, Albuquerque offers plenty of opportunity to discover its Spanish colonial heritage and Native American cultures. The Isleta Resort & Casino offers everything under one roof, with gaming, spas, golf, camping, live entertainment, fine dining and more.


Before reaching your next stop, visit the world’s best preserved meteorite impact site, dubbed Meteor City. Amazing views and a wealth of history just in the land itself is on hand to greet you in Flagstaff. Just south of the San Francisco Peaks, Flagstaff is situated right next to Mount Elden, the tallest mountain in Arizona.

Walnut Canyon is another natural marvel, with ancient dwellings and structures. The Wupatki National Monument is another fantastic piece of history, built by the Ancient Pueblo People. The museum of Northern Arizona and Riordan Mansion State Historic Park offer similar fields of expertise but in a more formal and structured environment with friendly and informative staff on hand. 

Grand Canyon

Next you’re heading North to one of the Seven Natural Wonders of the World, The Grand Canyon. At 277 miles long, up to 18 miles wide and depths of up to a mile, the Canyon is first hand accounting for nearly two billion years of earth’s history. Whether taking a heli tour or one via mule ride, there is plenty to be in awe at.

Las Vegas

By now, the name Las Vegas alone says it all. The glitz and glamour is everything you would expect and more. The cheesy entertainers of yesterday have been shown the backdoor and now permanent theatres show world-class shows.

The best singers, dancers, magicians, impressionists and cabaret acts in the world can all be found in Vegas
Away from the theatres there are still plenty of things to do. There are brand-new thrill rides, sumptuous pool complexes with wave machines, lots of golf courses and amazing shopping from designer boutiques to out-of-town factory outlet stores.

The romantic visitor can also pick up one of the 110,000 marriage licenses that are issued in Las Vegas each year… And if you are still not satisfied then of course there a couple of casinos!

Santa Monica

After that whirlwind tour you’ll be coming down the home straight to finish in Santa Monica. Third St. Promenade is fantastic for upscale shopping, dining and all forms of entertainment.

The Santa Monica Pier is still a classic landmark rooted in popular culture, deserving of a visit, and the beach is as popular today as ever with over three miles of room to play or relax upon.

Find a coming together of cultures at the Chess Park. While you’re here, grab some wheels like the locals, a Segway, skates or a bicycle to really appreciate the fineries of this beautiful city.

If you would prefer to begin your trip on the sunny west coast, then by all means you can take this trip in the opposite direction. Contact one of our experienced advisors now to enquire.

Route 66 Holidays

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