Route 66 Holidays

Self drive Route 66 bespoke holidays – packages including flights, car or bike hire staying in historic and character hotels & motels. Tailor made experts.  We have successfully planned hundreds of tailor made Route 66 holidays over the last few years, please get in touch now on 01728 748209 or complete the enquiry form or use the Live Chat to talk to us and start planning your Route 66 bucket list trip!

Whether you drive this route by car, motorhome or motorbike, this is the ultimate ‘all American’ road trip to self drive Route 66.  Crossing the USA from east to west covering over 2000 miles, get your motor running and ‘get your kicks on Route 66’! (See bottom of this page for price guidelines).


There are many fabulous fly drive holidays in the States but this has to be the biggest and best! We have driven parts of it around the canyonlands and it really is incredible (and Las Vegas has to be seen to be believed!). We can arrange for you to travel Route 66 on a Harley Davidson and really get the wind on your face or perhaps you want to take your time in a motorhome.  Maybe you saw  Billy Connolly on TV riding Route 66 which gave a wonderful view of the quirky sights and eccentric people that you could experience along the way! You can do this fly drive holiday most of the year though we suggest you avoid winter as some roads can be closed by snow and it’s not very pleasant in the cold (especially if you are on a bike or camping!).

Sometimes know as the ‘Will Rogers Highway’ after the humorist and also referred to as the ‘Mother Road’ or ‘Main Street of America’ this was just part of the US highway system until it became recognised in popular culture as the iconic drive that it is today. Road signs were erected in 1927 a year after it was originally established, running from Chicago to Los Angeles.  The hit song “get your kicks on Route 66” bringing worldwide fame to this road was originally recorded by the Nat King Cole Trio in 1946 and later coped by various artists including The Rolling Stones and Chuck Berry. Route 66 has had many changes and improvements over the years, altering the overall length and often detouring around cities to avoid congestion. In 1985 ‘US66’ was removed from the Highway System and replaced by the Interstate Highway System. 


Some sections of the former road have now been designated ‘Scenic Byways’ under the name ‘Historic Route 66’ and there are maps to help you through these sections. So where is the actual ‘Route 66’?  There are some deviations and of course with self drive holidays you can do your own thing, but here is our suggested ‘standard’ trip of  around 20 days which we can book and we use character and historic hotels and motels where possible. If you want different hotels or to deviate from the standard tour or just want the flights and car hire, that’s fine too, We can tailor make any version of your Route 66 holiday you don’t have to do the tour everyone else tells you to!

Here is a sample of one of our ‘suggested’ itineraries

Day 1  Arrive Chicago O’Hare airport. Make your way to your hotel downtown for two nights.

Day 2 At leisure – Chicago. Wander the shores of Lake Michigan, tour the skyscrapers and enjoy the magnificent mile of shops and restaurants.

Day 3 Collect your vehicle downtown Chicago.  Leave Chicago and drive through Springfield (note there are two Springfields on Route 66!). This one is famous for being the home of Abraham Lincoln.  Chicago to Springfield IL approx 200 miles

Day 4 Onwards to St Louis Missouri. Enjoy the sites of the famous Mississippi river and the Gateway Arch and Jefferson National Expansion Memorial if you want to go through the city. Or stay on Route 66 around St Louis into the land of the Ozarks. Overnight in Cuba a traditional small town on the route.  Springfield to Cuba approx 185 miles

Day 5  The Giant Rocking Chair (seen on Billy Connolly’s Route 66) is at US 66 Outpost in Fanning the other side of Cuba towards Rosati. Drive to Springfield Missouri through the Ozarks and Mark Twain National Forest stopping at small towns along the way.  Cuba to Springfield approx. 135 miles

Day 6  From Missouri drive through Kansas and Carthage and into Oklahoma (formerly Indian Territory) you may want to stop at Catoosa just before Tulsa to see the famous ‘Blue Whale’. 11th Street in Tulsa has some great Art Deco architecture and old R66 signs. Springfield to Tulsa downtown approx 185 miles

Day 7 On the stretch of road between Tulsa and Oklahoma there are various old loops you may want to stop along including the old towns of Chandler and Stroud. Visit the 1937 Armory with R66 Interpretive Centre in Chandler and the McJerrys R66 Gallery is just north of downtown. Oklahoma City has several cowboy and heritage museums – but you can bypass the city if you want.  Through Bridgeport and Weatherford to Clinton where you can visit the Oklahoma R66 Museum with a restored diner in the grounds. In Elk City is the National R66 museum and a huge neon sign.  Tulsa to Elk City approx. 220 miles

Day 8 Stop on the way at Mclean an interesting old town home to the ‘Devils Rope’ museum. Heading over the Texas panhandle you come to Palo Duro Canyon State Park and Amarillo – just outside the town is the famous ‘Cadillac Ranch’.  Elk City to Amarillo approx. 145 miles

Day 9 Leaving Amarillo make a stop just before the state border with New Mexico at the café at Adrian – the half way point of Route 66. There is a time change at the state line from Texas into New Mexico. Tucumcari has plenty of old picturesque motels. Amarillo – Tucumcari about 115 miles


Day 10 Travel across the plains, past the Sangre de Cristo Mountains to the Native Indian and arts centre of Santa Fe, the capital of New Mexico. Day at leisure around Santa Fe explore the many art and craft centres, galleries and shops. In the surrounding area you will find interesting national monuments and small parks. Tucumcari to Santa Fe approx 166 miles 

Day 11 A short drive today to Albuquerque and take in the neon lights of downtown which celebrates the American road culture of the 50s and 60s.  Santa Fe to Albuquerque about 60 miles

Day 12 Across the New Mexico desert on fabulous driving roads and you soon get to Gallup, the gateway to the Four Corners area and the Navajo Nation.  Albuquerque to Gallup 135 miles

Day 13  Just before Holbrook on Route 66 turn off to visit the Petrified Forest National Park. Then pass through Winslow (of Eagles song fame – “standing on a corner in Winslow Arizona”!). Just past Winslow is a turn off to the Meteor Crater.  Continue to Flagstaff today from where you can visit the Grand Canyon. Flagstaff has an historical centre.  Two nights here to allow time to explore the Canyon area. NOTE WE CAN BOOK YOU THE WIGWAM MOTEL AT HOLBROOK IF YOU PREFER. USA-wigwam

Day 14 Day at leisure exploring around Grand Canyon OPTION TO INCLUDE MONUMENT VALLEY AND OVERNIGHT AT GRAND CANYON:

OR/ Day 13 Head north from Gallup through Chinle, past Canyon de Chelly National Monument towards the Utah border. Near Kayenta you will find the most famous scenery of cowboy movies and road trips ever at Monument Valley! Gallup to Kayenta approx 160 miles

Day 14 Travel west across desert scenery through Tuba City to the Grand Canyon Village on the south rim. Kayenta to Grand Canyon approx 160 miles NOTE If you choose this option it’s about 340 miles from Grand Canyon to Las Vegas and I recommend adding a night at Peach Springs or Grand Canyon Lodge (west rim) on the way.

Day 15 Continue on Route 66 as it winds it’s way through some of the most scenic parts of it’s journey through Seligman around the edge of the canyon and Indian Reservations at Peach Springs to Kingman where you detour off Route 66 to Las Vegas. You will have two nights to allow time to wander up and down the world famous ‘Strip’ of Las Vegas. Flagstaff to Las Vegas 250 miles

Day 16 A day at leisure in Las Vegas Day 17 Heading back from Vegas to R66 re-join again at Kingman and take the old R66 as it switches back and forth down a river valley escarpment through Oatman (a gold mining town where you can see cowboy shoot outs and roadside Burros!), to the Colorado River valley. Las Vegas to Needles approx. 115 miles

Day 18 Follow the old rail road alongside Route 66 through Amboy, Bagdad (there are several ‘Ghost Towns’ on this last section of Route 66) and San Bernardino to the end of the road just before the Pacific Ocean. Turn into Sunset Boulevard and end at Santa Monica by the famous pier, there is where the road and America ends! Needles to Santa Monica approx. 275 miles

Day 19 A day to relax and enjoy Santa Monica and Los Angeles. Visit Beverley Hills and the famous sites of the area.  

Day 20 Drop your vehicle at Los Angeles airport and board your flight home.

Day 21 Arrive UK

Of course, this is YOUR trip so if you perhaps would rather skip anything or add anything, we can tailor make it exactly to YOUR requirements.

We have successfully planned hundreds of tailor made Route 66 holidays over the last few years, please get in touch now on 01728 748209 or complete the enquiry form or use the Live Chat to talk to us and start planning your Route 66 bucket list trip!

Whichever way you want to enjoy this fabulous road trip get in touch and we can arrange the ultimate fly drive American adventure. Remember you can do this route in either direction, but the more common choice is to start in Chicago.

Route 66 by Motorbike – We can arrange for individual bike hire or guided motorcycle tours of Route 66. The most popular bikes are Harley Davidsons, Honda Goldwing 1800 and the BMWUSA-R66-bikes-at-a-stop R1200GS. Rentals are charged per 24 hour period and all bikes come with Saddle Bags, Helmets (for driver and pillion) and include unlimited mileage and insurance. There are also group guided Motorcycle tours of Route 66. Route 66 by car – all types of standard rental cars are available from economy up to luxury and 4×4. We would include GPS in all our car hire. Some people choose to start with a saloon and swap for a convertible IF we can source one further down the route. Note that any convertibles will be modern models with very small luggage space! If you really must have a convertible, they are much easier to source in LA so please consider driving the Route west to east.

Route 66 by motorhome – Motorhomes or ‘RVs’ (Recreational Vehicles) are a popular way to self drive anywhere in America. For Route 66 we can book a variety of sizes to suit your group the biggest would usually sleep 6 people. If you have an HGV licence it may be possible to hire one of the huge ‘motor coaches’ used in the movies! Usually Personal kits (linen and towels) and Vehicle kits (crockery and kitchen essentials) are included. We give you a web link to check out the variety of camp grounds available along the route when you book. Note that motorhome depots are not open on Sundays and all operators require that you overnight in a hotel on arrival before collecting a motorhome. Motorhomes out of Chicago are difficult to source in peak season, the best time is April – May when there might be some ‘relocation deals’ we can use. On all vehicles our quotes will usually include the top level of insurance – details can be provided. If you are shopping around beware that some hire companies do not include things like essential items, cooking fuel and linen in motorhomes, decent insurance and local taxes on cars and bikes, etc. Cheapest is not always the best option!

PRICE GUIDELINES To give you a rough idea of prices for Route 66 holidays, on the standard 20 day itinerary, with a ‘normal’ (intermediate size 4 door saloon car), 2 people sharing a room, hotels along the way and transatlantic flights, you are looking at something in the region of £3,000 – £3,500 per person for travel in 2018, depending on the time of year, standard of hotels and flight fares.

We have successfully planned hundreds of tailor made Route 66 holidays over the last few years, please get in touch now on 01728 748209 or complete the enquiry form or use the Live Chat to talk to us and start planning your Route 66 bucket list trip!


We did it! Nearly 5 weeks, nearly 4000 miles, 23 beds ending at our regular holiday home resort near San Diego. Met some wonderful characters, seen a lot of sights and eaten in countless eateries, some really great and others perhaps not so. We actually met up with Jerry Mclanahan (author of EZ66) who duly signed our book and took photos, I was 66 that day, on Route 66 meeting the author! Some of the hotels were really wonderful. Loads of souvenirs, loads of photos to sort through and lots of memories and events to 'dine out on'. Thank you so much for your organisation, everything went well and worked seamlessly...
Dave & Nicki – Route 66 & San Diego (May 2017)
June 20, 2017

You picked some great places to stay we would probably not have found ourselves. Your local knowledge came in very handy when planning the itinerary - we would not otherwise have known the best direction to do the Pacific Highway nor thought of going to Laguna beach which turned out to be a brilliant place. Also the advice to get FastPass tickets for Universal. You made the booking of the flights and car very easy and those bits of the journey went very smoothly.
Davies Family – California (April 2017)
April 24, 2017

It was amazing and everything went like clockwork. The highlight was Noes Nest. I can't really describe how good it was. Breakfast was immense with such variety, taken in a large kitchen round the table with whichever guests were up at that time. The property is is a good area only 10 minutes from the city centre via the DART (tube), with loads of cool shops and bars within walking distance. It really was perfect. Alcatraz was immense. So in summary you nailed it again!
Waine Family – USA San Francisco (April 2017)
April 14, 2017

What a wonderful trip. Holiday of a lifetime. I can't thank you enough Jules and Mags. We thank you from the bottom of our hearts and we will certainly book another trip with you. It was awesome. You are awesome.
Violet & Craig – USA Route 66 (May 2016)
May 27, 2016

Our Route 66 trip was brilliant thank you. The driving was not as difficult as I expected - we bought the EZ66 guide in Joliet. Grand canyon was a great detour. I just enjoyed meeting the local people, they keep the route and history going, but not in a crazy way, just living on it.
Charlotte & Chris – Route 66 (July 2015)
September 1, 2015

Our tailor made Route 66 holiday was the best trip we have ever done - you did a great job at organising it, thank you! It was a great balance of accommodation with quirky motels, boutique hotels and historic sites. We would recommend anyone thinking about a trip down Route 66 to do it!
Tim, Anne, Paul and Emma – Route 66 (July 2015)
September 6, 2015

In my view life is too short NOT to use Julie's experience and contacts when booking a holiday! I couldn't recommend Travel With Jules more highly.
Nicky Fussell – several destinations (July 2015)
July 3, 2015

Our Route 66 holiday really was the trip of a lifetime and we will most certainly be booking our next trip with you!
Jack and Anita – Route 66 (April 2015)
July 20, 2015

We covered 1150 miles, discovered beautiful places and had such a great time we can't wait to save the money and do something similar soon. Thank you very much :)
Anna, Nigel and Sofia Alcalde-Mills – USA (April 2015)
June 12, 2015

I just wanted to write you an email thanking you for organising our ‘Route 66’ holiday. We had the most fantastic experience and it was all we wanted out of our weddingmoon and much much more. I could spend hours telling you about some of the unscripted experiences that I had such as a very […]
Sam and Alex Drohan – Route 66 ‘Weddingmoon’! (Oct 2014)
October 23, 2014

If I could only put into words what Jules and Mags did for me, I've no doubt that many more would use this company. I can only express that hand on heart, you will not regret it. No travel company I have previously used compares and I look forward to booking my next adventure through 'Travel With Jules'.
Steph & Sharon – USA Route 66 from Memphis (Sept 2014)
October 23, 2014

Just a quick email to say thanks so much for sorting out the accommodation, flights and cars for our Route 66 honeymoon. Everything was spot on! We wanted to turn around at LA and drove back to Chicago; it’s definitely something we want to do again. We’ve taken over 4200 photos!  All of the accommodation […]
Dan and Sonia Marsden – USA Route 66 honeymoon (Sept 2014)
October 23, 2014

Our holiday was great, thank you – Thanks for arranging everything and being very responsive with our issues whilst travelling – that was much appreciated. The highlights included the bikes (amazing!), riding through the passes and older roads – we did a great diversion into the Rockies north of Santa Fe – some of the old […]
McKenzie Family – USA Route 66 (Sept 2014)
October 8, 2014

Many of our travellers on Route 66 detour to the Grand Canyon – this ‘cowboy sleep out’ option is enjoyed from Grand Canyon Ranch at the west rim:  On the Cowboy Sleep Out, the best point is that this is run by a real cowboy.  Not the entertainer who tells stories over supper in the […]
McKenzie Family – Cowboy Sleepout USA (Sept 2014)
October 8, 2014

Our Route 66 self drive holiday was great, from Santa Monica pier LA to Chicago and everywhere in between. Thank you for organising the flights and the RV. The seats you managed to book on the flights were excellent and the RV from Cruise America was everything we had hoped for. Everybody had a turn […]
Wardle Family – USA Route 66 Motorhome (August 2014)
September 22, 2014

What a fantastic trip and adventure, we drove over 3000 miles saw all we could and met lots of nice Americans! Thank you for all your help and planning, you did a fantastic job from start to finish. Overall the hotels were a good mix, the Allegro in Chicago was excellent with a ‘wine hour’ […]
Tony & Max – USA Route 66 (July 2014)
August 22, 2014

The trip was brilliant and we wouldn’t hesitate to recommend you to arrange something similar for other clients. This was not a holiday was an adventure…a true road trip! 3500 miles all together. Upgraded to a Mustang convertible at Chicago to ensure the experience was fully authentic, thank you for working so hard to put the […]
John & Lisa – Route 66 (June 2014)
August 13, 2014

I virtually followed Route 66 from beginning to end as laid out in the EZ66 Guidebook that you recommended, and got a real feel for mid 20th century America. I also managed to pack a lot in as well as the route itself. I went on an Architectural tour of Chicago, up to the top […]
Adrian Fairhurst – USA Route 66 (May 2014)
June 3, 2014

Really enjoyed our trip down Route 66, everyone we met was very friendly and helpful. It was an adventure as well as a holiday and we both really enjoyed the trip, I’m so glad we did it.  Thank you for all your efforts in organising it. We used as recommended, the EZ66 Guide for Travellers […]
Keith and Rachel – USA Route 66 (April 2014)
June 3, 2014

Well I'm now in Chicago and have had an awesome time. It's been full on and clocked up around eight thousand miles. Thank you again you're a travellers champion!
John Oliver – Route 66 LA to Chicago (March 2014)
March 31, 2014

We had the time of our lives. It was all terrific. We were typical tourists and crammed in as much sight seeing as was possible! Thanks for all your help in organising this trip. It made it much easier and you gave us the confidence to go "off piste".
Viv & Nikki – Route 66 & California (Sept 2013)
December 13, 2013

We had every confidence in you and trusted you implicitly. It was so reassuring knowing you were there for us throughout. Arranging our flights, travelling, bike hire and accommodation from Chicago to LA, over 2,000 miles all the way - you did this with great care and attention. We thank you from the bottom of our hearts. We would highly recommend you to all our friends and family.
Sue & Simon – Route 66 (Sept 2013)
July 22, 2014

We are back…! We just couldn’t wait to tell you how thrilled we were with our Route 66 experience - Thank you for all your hard work in the organising of it, it was an experience neither of us will ever forget.
Mick & Jaclyn – USA Route 66 (September 2013)
October 13, 2013

We can't thank you enough though with your help and patience at all hours in organising it all. It was the trip of a lifetime!
Kris & Rosemary – USA Route 66 (September 2013)
October 5, 2013

A thousand thank you’s for arranging our recent trip on the mother road! What an amazing adventure. From start to finish your arrangements were perfect. We saw parts of the world we will probably never see again and were completely in awe. From Chicago to LA a wonderful holiday. The Gateway Arch, Mississipi River Boat, […]
Keith & Sheila – USA Route 66 (September 2013)
September 24, 2013

Everything was perfect, from the flights, to the car rental, and to the superb hotels. We had a great time and saw some AMAZING sights ... Thankyou so much for your help in pulling this together for us
Jim ‘Essex’ – USA West Route 66 (July 2013)
August 7, 2013

We had a truly memorable time and everything went relatively like clockwork. It was very comforting to turn up and be expected at all locations. Like everyone we guess we would have tweaked things a little with the benefit of hindsight, but overall extremely satisfied.  Our journey took us all around California, along the Pacific […]
John, Mandy, Martin & Fay – Western USA fly drive (July 13)
November 24, 2013

What can I say but a massive thank you for your help and advice with our trip of a life time honeymoon! Even though we have never meet the service you gave us was just like talking to a friend.....
Jo & Theresa – Route 66 & San Francisco USA (June 2013)
August 22, 2013

We found Julie by chance after searching “route 66 holidays” and are we glad that we did. With relatively short notice Jules really did create a holiday of a lifetime for us. We had some ideas of what we wanted to do, such as sleeping in a concrete wigwam, detouring to Monument Valley and also […]
Sarah & Jeremy White – USA Route 66 (June 2013)
September 7, 2013

We absolutely loved our recent trip along Route 66 organized for us by Travel with Jules! The holiday was perfectly paced and flawlessly organized, and I am really glad that we chose Travel with Jules for our Route 66 experience!
Pam and Pete Drummond – USA Route 66 (June 2013)
June 25, 2013

Leaving Jules to organise our Route 66 trip turned out to be a great decision, she quickly and efficiently put together an itinerary which we were able to tailor together to meet our needs. We had a great time seeing so much of America and meeting some nice people along the way. All went to […]
Mark Tonge – USA Route 66 (June 2013)
June 25, 2013

If, like me, you’ve stumbled across Julie’s website after doing a search for a holiday experience, don’t waste any more time looking for your perfect holiday organiser – you’ve found her! Nothing seemed like too much trouble; plenty of ‘what ifs’ posed and responded to with an immediate understanding of what we were looking for. If you’re looking for a travel organiser to tailor your holiday to your requirements, look no further than Jules – thoroughly recommended.
Andy & Graham – Route 66 USA (September 2012)
October 19, 2012

Julie has been the most helpful, patient & greatest person to organise this trip for me & my best friend Liz. We have just returned back from the USA, driving Route 66, WOW, what an adventure Julie organised for us!
Caroline Gorner – USA Route 66 (June 2012)
June 24, 2012

One of the things I have come to love about you, Jules, is that you listen and take on board what makes me tick, and then tailor the holiday to fit me, not just try to convince me to fit a holiday in a brochure!
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