Route 66 Holidays

Get Your Kicks on a Route 66 Holiday.

See iconic America at its finest with a Route 66 holiday from Bon Voyage. Because who can resist this classic 2,448 mile journey through eight states and three time zones?

Route 66 dates back to 1926, long before the Interstates were conceived and built. In those days it was possible to journey from the Midwest to the California Coast by one road - Route 66 - right through small town America and the heart and soul of the USA. Much of the original road can be re-traced today, so you can follow in the tyre tracks of those who made the road famous.

Watch the video below to see our very own resident American - Theresa - talk you through the main things to take into account when considering a Route 66 holiday.

Route 66 Itinerary from Chicago to LA

All the best Route 66 fly drive holidays start in Chicago where the road originally began at the corner of Jackson Boulevard and Michigan Avenue in 1926. Travelling from Chicago to St Louis, Missouri, the icons of Route 66 that you've seen on television and read about in books appear before your very eyes.

Next on your Route 66 itinerary is a Cross into Missouri by way of the historic Martin Luther King Memorial Bridge. In St Louis, be sure to visit the top of the Gateway Arch for spectacular views of the mighty Mississippi River. The American diner experience is also one not to miss. Sweetie Pies, owned by one of Tina Turner's "Ikettes" Ms Robbie Montgomery, is always fun. There’s also Blueberry Hill, filled with pop culture memorabilia and live music.

From St. Louis to Springfield, Missouri the lush rolling hills of the Missouri Ozark Mountains appear much as they did when the first settlers arrived in the late 1800s. Leaving Missouri for Oklahoma, which boasts the longest stretch of original Route 66 miles, the landscape begins to change from the rich croplands of the Midwest to the red, dry dusty Southwest.

Cross into the Lone Star state of Texas and arrive in the heart of Cowboy Country and quirky Cadillac Ranch. If you're seeking cracking scenery, be sure to take a short diversion to Palo Duro Canyon State Park, one of the most beautiful places in Texas. Here you'll learn about the Apache, Kiowa and Comanche tribes who took refuge here.

Approximately 30 miles from Holbrook, Arizona is fascinating Meteor Crater. The 500-foot-deep hole was created by a meteorite 22,000 years ago! Okay, no match for the Grand Canyon, but that's coming! Have your picture taken "Standing on the corner of Winslow, Arizona” where you'll find a statue of a guy with a guitar and a mural of a girl (my lord!) driving by in a flatbed ford. We guarantee it will have you humming the Eagles hit as you drive off.

The Grand Canyon and beyond.

And now… at 277 miles long and 6,000 feet deep welcome to the Grand Canyon, the granddaddy of natural wonders encompassing over 1.2 million acres.

Whilst it's not technically ON Route 66, who could possibly miss out on Las Vegas? Las Vegas has been the biggest boomtown in the history of the world. Love it or hate it, there's no denying that this place will blow your mind and be a true highlight of any Route 66 fly drive holiday.

Finally, after a journey through the Mojave desert, over mountains and through the lush inland valleys of California, you will reach the bright lights of Hollywood and the beautiful beaches of Santa Monica. It's here where Route 66 meets the Pacific Ocean and all epic Route 66 fly drive holidays must end.

When should I drive Route 66?

A Route 66 holiday should be kept between May and October to avoid snow in some states, and attraction closures in others.

To complete the journey from start to finish you’ll need a minimum of 14 nights, and you’ll need to do some driving each day. However, anything is possible with a tailor-made holiday from Bon Voyage, so we can create longer or shorter trips to suit you.

Drive Route 66 in comfort or style

You’re driving from one side of the States to another, so a roomy, comfortable and powerful car is essential. If you have your heart set on a convertible, we can incorporate this for part of your journey - so you can experience the best of both worlds.

We can also organise a self drive, or guided tour on a Harley-Davidson, all you need is a valid UK motorcycle licence. Another popular option is a motorhome, but this does mean you miss staying in classic or quirky accommodation along the way.

There are many options on a Bon Voyage Route 66 holiday. Shorter and extended versions, Harley Davidson self-drive and guided tours, plus an escorted coach tour. Have a look at our sample itineraries - all of which can be tailor-made to your exact specifications.

Spice up your Route 66 trip with a 4x4 and convertible combo

From the start of Route 66 in Chicago, enjoy the extra room and power of a mid-size 4x4, there's a lot of miles to cover afterall. When you reach Vegas, swap it for a cool convertible. Flip back the roof, throw on the Ray Bans and enjoy the desert sunshine as you cruise into California!