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. 

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 BMW 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!