Route 66 Holidays

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Route 66 Holidays

Route 66 holidays in 2024/2025. Drive along the Mother Road, the Main Street of America, the Will Rogers Highway - Route 66 has been known by many names over the years, and to this day it still remains a classic American road trip covering 2448 miles through 8 states: Illinois, Missouri, Kansas, Oklahoma, Texas, New Mexico, Arizona, California... and also the bonus state of Nevada which many choose to detour to and visit Las Vegas!

Your 2024/2025 Route 66 Road Trip begins in Chicago, Illinois and runs all the way across the country to Santa Monica, California. Along Route 66 you'll find many classic Route 66 motels which provided rest-bite for travellers of Route 66 during its heyday- some motels were even visited by the likes of Elvis Presley on his Route 66 road trip!

How Long You Will Need

2024/2025 Holidays driving along Route 66 include driving the entire thing or just completing sections. Travellers who don't have an extended period of time for their holiday often like to complete Route 66 backwards and do Santa Monica to Phoenix Arizona (the Mini Route 66 Road Trip) as this allows them to see the majority of the Route 66 highlights including the Santa Monica Pier, the city of Los Angeles, Roy’s Café in Barstow, Las Vegas, the town of Chloride – the oldest inhabited town in Arizona, the iconic Hackberry General Store, Pete's Route 66 Gas Station Museum in Williams, Flagstaff, the amazing Grand Canyon National Park, and more! To do this Route 66 road trip we would recommend 14 nights as this allows you to stay for multiple consecutive nights in areas like Santa Monica, Las Vegas, and the Grand Canyon whilst also making stops along the way for one night at the various Route 66 towns and motels.

Route 66 road trip in 2024/2025 from Chicago to Santa Monica or indeed from Santa Monica to Chicago, though it can be done in 14 nights with singular night stopovers and a couple of consecutive night stays in bigger cities, a three-week holiday would be better suited as this allows you to really explore each location and take-in the journey of Route 66 by not rushing and spending more than one night at each stop. The highlights for the entire Route 66 journey include all of the above plus the iconic Gateway Arch in St Louis, the historic Wagon Wheel Motel, the Rail Haven Motel where Elvis Presley stayed, the quaint town of Galena and its Disney’s Cars tribute, the National Route 66 Museum, the iconic U-Drop Inn/Conoco Tower, the Leaning Tower of Texas, the city of Albuquerque, Six Flags St. Louis, the Route 66 Ends Here sign in Chicago, the MidPoint Café, and more!

2 WEEKS – Mini Route 66 Road Trip or The Entire Route 66 with 1 Night stopovers

3 WEEKS – The Entire Route 66 Road Trip with multiple night stopovers

What Vehicle to Drive

Route 66 driving holidays in 2024/2025 offer multiple ways to do this but the way our clients love the most is driving in an SUV as this gives you the most comfort whilst making the long journey. Sometimes clients will say they want to drive the iconic Route 66 in a convertible or a sports car, to this we suggest driving Route 66 backwards so you can drive from Santa Monica, California to Las Vegas, Nevada in style and then switch to comfort from Las Vegas to Chicago as the drive is much longer and often at times through vast stretches of desert. Another popular option is driving Route 66 on a Harley-Davidson*, a classic American motorbike, which again we would suggest to be done for a specific leg of the journey like from Santa Monica to Las Vegas (or Las Vegas to Santa Monica). Another alternative travellers often decides to do is drive Route 66 in a classic American RV (motorhome) – this gives you the option to stay in both the quirky and modern hotels along the way and also your own motorhome if you find somewhere, without a hotel perhaps, you want to stay for the night.

*Valid UK motorcycle licence needed

The Best Time to Go

The best time to do your 2024/2025 Route 66 holiday is during the spring and autumn months: April, May, June and then September and October, this is because in the California and Arizona desert in the summer it can get very hot and in the winter in Illinois, Missouri, Kansas, Oklahoma it can get very cold with snowfall. If you are planning on only doing the Mini Route 66 Road Trip from Santa Monica to Phoenix through California up into Nevada and down into Arizona then you are unlikely to encounter very cold weather at any time throughout the year - at night-time Nevada and Arizona temperatures will drop but during the day they will remain fairly mild, at least compared to English winters.

For more information for on your Route 66 road trip, why not get in touch with one of our Travel Advisors and speak to a Route 66 Specialist who will be able to answer any of your questions.

Best Selling Route 66 Holidays Itineraries

Route 66 Shorter Road Trip

Quote CHH1287
Enjoy this 14 night Route 66 shorter road trip from Santa Monica to Scottsdale. Visit Las Vegas, Kingman, Seligman and Williams on the way.

Route 66 Holiday Santa Monica to Chicago

14 Nights
Quote CHH1286
Enjoy this Route 66 holiday in reverse, start in Santa Monica and end in Chicago taking in old and authentic buildings, shops, cafes and motels. You really will feel as if you have stepped back in time

Route 66 Self Drive Tour

15 Nights
Quote CHH459
Experience a real holiday in America on this Route 66 Self-Drive tour. Travel along the famous Mother Road of Route 66, starting in Chicago and ending in Los Angeles, with many cities and sights along the way

Route 66 From Chicago to California

Quote CHH1285
Stretching from Chicago's skyscrapers to Santa Monica's pier, take this 18 day/17 night itinerary Route 66 holiday on a nostalgic journey through the heart of America

Stops Along Route 66

Route 66 Holidays
Route 66 Flagstaff Arizona

One of Arizona's most loved cities, Flagstaff is a must see on your Route 66 tour. As well as being a great location in its own right, Flagstaff is your gateway to many other Route 66 attractions including the Grand Canyon National Park, Phoenix, the historic town of Sedona, amazing sights like the Meteor Crater Natural Landmark and more!

Route 66 Holidays
Route 66 MidPoint Cafe
The MidPoint Café is halfway between Santa Monica and Chicago and is a great place to enjoy an authentic American dining experience at a Route 66 diner. At MidPoint Café you will likely meet other Route 66 travellers with whom you can discuss what you've seen so far and what to look out for as you finish your Route 66 road trip
Route 66 Holidays
Illinois Route 66 Hall of Fame and Museum at Pontiac

There are many museums to visit along Route 66 but the Illinois Route 66 Hall of Fame and Museum is one of the best. Illinois is near the beginning of the Route 66 road trip, so it’s a great place to learn about the historic road and journey you are about to embark on.

Route 66 Holidays
Route 66 Gateway Arch St Louis
The Gateway Arch is located in the city of St. Louis, and is one of the most famous National Monuments in the USA. St. Louis is a bustling city full of historic and modern architecture, including renovated buildings with family attractions like mini golf and an aquarium, that you will be able to stop at early on in your Route 66 road trip if you are beginning in Chicago
Route 66 Holidays
Route 66 Petrified Forest National Park

The Petrified Forest National Park is located in Arizona and is home to fascinating archaeological sites and a beautiful multi-coloured landscape. It is also where you can drive along Historic Route 66 and get a feel for the original Mother Road.

Route 66 Holidays
Route 66 The Grand Canyon Arizona

Detour to The Grand Canyon Arizona on your Route 66 holiday! Visiting the Grand Canyon National Park is a bucket list item for when you visit the USA, and this is a great opportunity to see this natural wonder. 

Route 66 Holidays
Santa Monica The End of Route 66

Route 66 finishes in Santa Monica, specifically on the Santa Monica Pier; the Route 66 Trial Ends Here sign provides a great photo-opportunity for Route 66 travellers. From Santa Monica you can also explore the city of Los Angeles, including seeing the Hollywood sign, driving down Rodeo Drive and much more.

Route 66 Holidays
Route 66 Williams Arizona

Williams is a small town in Arizona, and if you are travelling Route 66 back to front (from Santa Monica to Chicago) you will come across Williams before the city of Flagstaff. Williams is the little brother to Flagstaff, and also is known as the second gateway to the Grand Canyon. 

Route 66 Holidays
Route 66 Scottsdale and Phoenix Arizona

Scottsdale/ Phoenix Arizona are not on the traditional Route 66 road however a slight detour will have you there in no time. This is a great detour to make as on your way to Scottsdale/ Phoenix Arizona you will see some other Arizona highlights including the small town of Sedona and some historically significant architecture.

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