Our RideFree experience was an adventure of epic proportions. With the guidance of Wil and strategic planning, we managed to do a self-guided tour from LA to Yosemite National park,... read more through San Francisco and back down to LA in 5 days. It was a trip of a lifetime and I can't wait to hit the road again soon."
Read my full blog and story here on my website, NavigatorNick
Nick S 4/24/2020
Nathan Peach ( Overseal, Derbyshire, United Kingdom ) Just recently completed a Ride Free organised tour of Northern California, me and my buddy hatched an idea to go... read more and have an adventure in America whilst still fit and able enough to not be plagued with...More
nathanp265 11/11/2019
Wil and Erin at Ride Free organised our whole trip along route 66 then the coast road to San Francisco. A self guided driving tour we did with our friends.... read more And taking in some of the natural wonders as well like the Grand Canyon &...More
Hello Wil and Erin. Just a short note to thank you for the ‘BEST VACATION EVER’. Both Brian and Andy were exceptionally professional and it is fair to say that that trip would not have been as good without the professional and friendly banter between the group and the guides. They were well able to cater for the differences in the group and this aided the holiday. The locations, lodgings and roads traveled matched and, sometimes, exceeded our expectations. On at least two occasions the accommodations were part of our dreams. ( Log cabin on a lake ) Read More
Custom Classic Car Rental and Tours for you or your group. We arrange it all, just like our motorcycle tours. Contact us To join a current classic car tour we have planned, or to book a custom tour for your group.
Ride the Pacific Coast Highway in a Classic Car, or cruise route 66 in a classic car rental. We rent the classic cars on guided tours along the California Coast Pacific Coast Highway. Or drive RT 66 in a classic car rental. Ride Free Tours leads the group in a classic car, and we have a fully equipped mobile shop with trailer, parts, and a classic car mechanic that follows the group. All you have to do is have fun. We take care of the classic car rental, route, hotels, any worries, and anything that happens along the way.
Route 66 Guided Car Tour. Drive Historic Route 66 from Chicago to LA down the Mother Road of America. Explore old Rt 66, The Grand Canyon, Las Vegas, and more with the Oldest Motorcycle Tour Company in the USA. Fully Insured.
See the Route 66 Guided Motorcycle Tour from Chicago to Los Angeles with Las Vegas and the Grand Canyon. Or for a shorter Route 66 trip, you can join on a motorcycle the portion from Albuquerque to LA on Route 66. This is a 10 Day Tour.
Pre Rt 66 Trip to Harley-Davidson Museum in Milwaukee – or – Milwaukee Start Option – add to any tours
This extra day pre trip is available as an option on all our Route 66 tours. Adds 1 or 2 days to trip.
Or Start the tour in Milwaukee, visit the Harley Museum, pick up the bikes, ride with the group to Chicago.
Harley-Davidson 115th Anniversary Celebration Museum Rally Route 66 Motorcycle Tour from Milwaukee
Part 1: We meet up for a few days of celebration at the Harley Museum in Milwaukee. Then we get our bikes and ride to Chicago.
Part 2: From Chicago we do the Route 66 Chicago to Los Angeles Harley-Davidson Motorcycle Tour
Option 1 – 15 Day 14 Night – Traditional Classic Route 66 Motorcycle Tour
– can add Milwaukee Harley Museum Option
This is the Traditional Route 66 Chicago to LA Harley-Davidson Motorcycle Tour. Ride Free includes almost a full day at The Grand Canyon on this motorbike trip across America, or explore the area on your bike that day. And, we arrive early to Las Vegas so you have a full afternoon and night in Las Vegas, or we can ride the Red Rock Canyon by Vegas or The Valley of fire. Optional helicopter ride at Grand Canyon. This is what most motorcycle tour companies run, but we highly suggest the 16 day or 17 day tour. They turn the trip from a mission feel where you just don’t have the time you wish you had every day, into the motorcycle tour experience you were hoping for. It is not that our 16 day Rt 66 route is longer in mileage, we just give you more time to see the things you came to see, and not be exhausted like the other tours we see on the road.
Option 2 – 16 Day 15 Night – Ultra Route 66 Motorcycle Tour – or 17 day Ultimate Explorer
– can add Milwaukee Harley Museum Option
This is the traditional Route 66 Chicago to Los Angeles Motorcycle Tour, BUT with a couple of extras.
We explore Rt 66 where most tours ride right by, and we add days so we have time to explore more without days being too long on our motorcycles. # Wil highly recommends this over any 15 day Rt 66 Route.
We add a day in the middle of the trip = shortens the riding days. Our 15 day is the industry standard, but there are some very long riding day, if you add a riding, it will make the 3 long days into 4 nice days. Well worth it. Or add 2 extra riding days for a 17 day Route 66 Motorcycle Tour, and is even more relaxing. This is how Wil would choose to do it every time. You are only doing this once, believe me now or later…
## Note: don’t let the mileage fool you, much of our trip exploring is slow moving and takes a long time. And, you don’t want to miss all the history and attractions.
Option 3 – 13 Day 12 Night – Chicago to Las Vegas Rt 66 Motorcycle Tour
– can add Milwaukee Harley Museum Option
This motorcycle trip across America is the same as the Traditional Chicago to LA Route 66 Harley-Davidson
motorcycle tour, but we ride our motorbikes Chicago to Las Vegas on Route 66.
Option 4 – 10 Day 9 Night – Chicago to Albuquerque Rt 66 Motorcycle Tour
– can add Milwaukee Harley Museum Option
This motorcycle trip across America is the same as the Ultra Chicago to LA Route 66 Harley-Davidson
motorcycle tour, but we ride our motorbikes Chicago to Santa Fe / Albuquerque on Route 66.
Option 5 – 9 Day 8 Night – Albuquerque to Los Angeles Rt 66 Motorcycle Tour
This motorcycle trip across America is the same as the Ultra Chicago to LA Route 66 Harley-Davidson
motorcycle tour, but we ride our motorbikes Albuquerque / Santa Fe to Los Angeles on Route 66.
Option 5B – 10 day 9 Night – We go to Santa Fe also on this trip.
Option 6 – 19 Day 18 Night – Chicago to Los Angeles Ultimate Rt 66 Motorcycle Tour
Add Harley Museum and Las Vegas Layover – starts in Chicago or Milwaukee start option
This Rt 66 motorcycle trip across America is the same as the relaxed 17 day Ultimate Chicago to LA Route 66 Harley-Davidson Motorcycle Tour, except we add in a stop at the Harley Davidson Museum in Milwaukee and a layover day in Las Vegas.
If you want to go no holds barred on your motorbike experience of a lifetime, this is the trip for you. It still also has the layover day in Santa Fe. You will have time to see so much on your trip, and with the layover days, you will be much less fatigued and tired than the 15 day trip.
We meet after lunchtime at the hotel and talk about our upcoming adventure on the Mother Road of America, Route 66 Chicago to LA. We also do an orientation with the classic cars to familiarize ourselves with the upcoming adventure on Route 66 in cars like 1965 Mustang Convertibles. Then we go out for dinner after checking out the beginning of Route 66 in downtown Chicago to discuss our big adventure!
Day 2 – Chicago to Springfield, Illinois
Let’s get in our classic cars and drive on Route 66! We settle into our classic car rentals , and aim for California. This is our first night on the road. See icons such as the “Gemini Giant”, “Rocket Man”, “Old Log Cabin”, the old “Marathon Oil Station”. We also stop at the RT 66 Museum in Joliet.
That afternoon we arrive to Springfield and stay at a nice local hotel in historic downtown where we can visit the amazing Lincoln Museum if we have time before having dinner at a local restaurant and celebrate our first night on the road.
Day 3 – Springfield, Illinois to Saint Louis
Riding Rt 66. Exploring St. Louis. The Gateway Arch welcomes travelers heading East or West. Maybe a blues bar tonight?
Before we get to Saint Louis, we drive out classic cars with the top down to the historic Chain of Rocks Bridge. We will walk out on the old bridge!
Day 4 – St Louis to Lebanon, MO
Riding Rt 66 through neat little towns. We have really fallen into sync with our vintage rides now.. Americana. How about some great American BBQ? We get a picture with the worlds largest Rocking Chair. Devils Elbow is amazing. This is small town America. At a glance it does not seem like much has changed. We hang out with the locals tonight and relax under the stars under some neon light of a vintage Rt 66 Motel in the countryside.
Day 5 – Lebanon to Tulsa, OK 233 miles
Great section of RT 66 with all the Googie Architecture. A really great ride. Great old diners. A really nice driving day. This is one of the longest days, but a great day. This is RT 66! We stop and meet some very interesting people along the ride today, and ride over a famous RT 66 Bridge in our classic cars. Then we go stop at a great little motorcycle museum along the way that has a great history of Rt 66.
Day 6 – Tulsa to Clinton OK 191 miles
Today is a really nice cruise through the countryside. So many great little signs and remnants of the hay days of this great road to see. We end the day with the Oklahoma Route 66 Museum where we can travel in time back to the glory days of Rt 66.
Day 7 – Clinton to Amarillo, TX
In the morning after a short ride we visit the Elk Cit Rt 66 Museum. I could spend a day at this one. It is absolutely amazing. The farming history, Wild West History, and every aspect of old America. Welcome to Texas! The panhandle of Texas. Big Texan Steakhouse for dinner? Everything is bigger in Texas. You will know you are on old Rt 66 today. It will feel like a throwback to what it was like to travel Rt 66 on the road in years past.
DAY 8 – Amarillo to Santa Fe, NM
Cadillac Ranch is a Route 66 stop we must do. Who has ever spray painted a vintage Cadillac on Rt 66 before? Let me ask you again in the future… Midpoint of Rt 66 at the Midpoint Café! Amazing day of vintage hotels and neon signs like The Blue Swallow and others. Welcome to Santa Fe. Art galleries, great restaurants, great walking around…. This is really an amazing Southwest city to spend time in. We discover the rich history and culture of Santa Fe after a big day riding Route 66 in our classic cars.
DAY 9 – Santa Fe Layover
Day 10 – Santa Fe to Gallup
We follow the Route 66 path, and end at the little town of Gallup, at the Rancho Hotel.
The historic El Rancho Hotel and Motel has hosted a numerous array of movie stars including John Wayne, Ronald Reagan, Humphrey Bogart, Spencer Tracy, Katharine Hepburn, Joan Crawford, Kirk Douglas, Doris Day, Gregory Peck, and Burt Lancaster. The rugged terrain surrounding Gallup was popular with Hollywood film makers during the 1940’s and 1950’s for the on-location shooting of Westerns. Actors and film crews would stay at the hotel during filming.
Day 11 – Gallup to Grand Canyon National Park
First, we will stand on a corner in Winslow, Arizona. We will get pictures with you and your classic car on a corner in Winslow, Arizona.
Next we drive down the main drag on Rt 66 in our vintage Mustang Convertibles with the top down through Flagstaff. Then, we stay on top of the Canyon and watch the sunset the first night. The Grand Canyon. “That’s one big hole!”, enough said. Seeing the sun set over the Grand canyon is one of the things that everyone should see once in a lifetime. We have dinner right on the rim of the Canyon. At night, we can walk back over to the rim under the stars.
Day 12 – Grand Canyon to Williams, AZ
What is different about Ride Free Chicago to LA Route: We stay at the top of the Grand Canyon for the sunset, unlike most tours who only stay at the bottom. We also spend a whole day at the Grand Canyon the next day, then ride to the bottom so we have more time on an amazing part of Route 66 the next day. For those that want to ride more, we have an amazing ride set up for the day.
Who is up for a helicopter ride across the canyon after watching the sunrise?
Hike down a trail the next am. into the Grand Canyon. Ride the donkeys down the trail into the canyon? Just relax enjoy the sites and history.
Check out the Watchtower. Lots of great things to see. We get a full day in The Grand Canyon. When we are done here, we start heading back down the mountain and stop if you want for a helicopter or plane ride into the Canyon. Or maybe an old train ride? We then work our way down the hill after an amazing day to Williams for dinner and a night on the little town. Or sleep. Ready to hit the road the next am for an amazing day.
Day 13 – Williams to Laughlin, NV
An amazing Old RT 66 day! All the RT 66 shopping you could think of. We will be on the forgotten RT 66 a lot of the day. Grand Canyon Caverns, Peach Springs, Kingman…Towards the end of the day we will work our way on an incredible slow winding road to the old mining town of Oatman. Wild burros, real old 49er gold miners with real Colt 45s on their hips to protect their gold. A forgotten town. Not much has changed here the past 100 years. It is almost unbelievable that is winding mountain road was the main East West road until 1953 when Rt 66 was re routed. Time has held still since then in Oatman.
Laughlin is a little Gambling town on the way to Vegas on the Colorado River. Let’s get you ready for the Big Time tomorrow. Ribeye Steak tonight!
Day 14 – Laughlin, NV to Las Vegas, NV
An early morning ride out beats the heat, and gets us to Vegas early for a full day…. Plenty of time relax in your Vegas room and get cleaned up before hitting the Vegas Strip. Of course we get a picture in from of the famous Las Vegas sign when we ride in town down the strip on our Classic Cars. Or, instead of just Vegas lounging, we have some great rides out from Vegas if you want some more cruising our vintage Mustangs in Las Vegas. Like Red Rock Canyon and some other stops.
But first the Hoover Dam! Vegas – Pools, shows, fun. We will have most of the day to explore Vegas, and the whole relaxed evening.
Day 15 – Las Vegas, NV to Big Bear Lake (or Victorville), CA
We follow the original path of Old Route 66 where we explore the amazing Mojave desert. If we do the Big Bear Option we climb into the cool Alpine town of Big Bear Lake at the end of the day.
Day 16 – Big Bear Lake (or Victorville) to Santa Monica Pier!
Over the famous Cajon Pass, then we drop into LA, freeways, civilization. We make it through all the way to the end. The Santa Monica Pier. We can go to Hollywood Blvd today, or we can explore the refreshing California Coast. Malibu, Venice Beach, Santa Monica… let’s keep the Ride Free tradition of ending the tour by putting our feet into the cold Pacific!
We turn the cars in at the end of the day.
Let’s celebrate tonight!
Day 17 – Los Angeles Departure
We say our goodbyes, and plan for our next adventure. There is so much more to see in the USA in the future.
We meet after lunchtime at the hotel and talk about our upcoming adventure on the Mother Road of America, Route 66 Chicago to LA.
We also do an orientation with the classic cars to familiarize ourselves with the upcoming adventure on Route 66 in cars like Mustang Convertibles.
Then we go out for dinner after checking out the beginning of Route 66 in downtown Chicago to discuss our big adventure!
Day 2 – Chicago to Springfield, Illinois
Let’s get in our cars and drive on Route 66!
We settle into our car rentals , and aim for California. This is our first night on the road.
See icons such as the “Gemini Giant”, “Rocket Man”, “Old Log Cabin”, the old “Marathon Oil Station”. We also stop at the RT 66 Museum in Joliet.
That afternoon we arrive to Springfield and stay at a nice local hotel in historic downtown where we can visit the amazing Lincoln Museum if we have time before having dinner at a local restaurant and celebrate our first night on the road.
Day 3 – Springfield, Illinois to Saint Louis
Riding Rt 66. Exploring St. Louis. The Gateway Arch welcomes travelers heading East or West. Maybe a blues bar tonight?
Before we get to Saint Louis, we drive out cars with the top down to the historic Chain of Rocks Bridge. We will walk out on the old bridge!
Day 4 – St Louis to Lebanon, MO
Riding Rt 66 through neat little towns. We have really fallen into sync with our rides now.. Americana. How about some great American BBQ? We get a picture with the worlds largest Rocking Chair. Devils Elbow is amazing. This is small town America. At a glance it does not seem like much has changed. We hang out with the locals tonight and relax under the stars under some neon light of a vintage Rt 66 Motel in the countryside.
Day 5 – Lebanon to Tulsa, OK 233 miles
Great section of RT 66 with all the Googie Architecture. A really great ride. Great old diners. A really nice driving day. This is one of the longest days, but a great day.
This is RT 66! We stop and meet some very interesting people along the ride today, and ride over a famous RT 66 Bridge in our cars. Then we go stop at a great little motorcycle museum along the way that has a great history of Rt 66.
Day 6 – Tulsa to Clinton OK 191 miles
Today is a really nice cruise through the countryside. So many great little signs and remnants of the hay days of this great road to see. We end the day with the Oklahoma Route 66 Museum where we can travel in time back to the glory days of Rt 66.
Day 7 – Clinton to Amarillo, TX
In the morning after a short ride we visit the Elk City Rt 66 Museum. I could spend a day at this one. It is absolutely amazing. The farming history, Wild West History, and every aspect of old America. Welcome to Texas! The panhandle of Texas. Big Texan Steakhouse for dinner? Everything is bigger in Texas. You will know you are on old Rt 66 today. It will feel like a throwback to what it was like to travel Rt 66 on the road in years past.
DAY 8 – Amarillo to Santa Fe, NM
Cadillac Ranch is a Route 66 stop we must do. Who has ever spray painted a vintage Cadillac on Rt 66 before? Let me ask you again in the future… Midpoint of Rt 66 at the Midpoint Café! Amazing day of vintage hotels and neon signs like The Blue Swallow and others. Welcome to Santa Fe. Art galleries, great restaurants, great walking around…. This is really an amazing Southwest city to spend time in. We discover the rich history and culture of Santa Fe after a big day riding Route 66 in our cars.
Day 9 – Santa Fe Layover
Day 10 – Santa Fe to Gallup
We follow the Route 66 path, and end at the little town of Gallup, at the Rancho Hotel.
The historic El Rancho Hotel and Motel has hosted a numerous array of movie stars including John Wayne, Ronald Reagan, Humphrey Bogart, Spencer Tracy, Katharine Hepburn, Joan Crawford, Kirk Douglas, Doris Day, Gregory Peck, and Burt Lancaster. The rugged terrain surrounding Gallup was popular with Hollywood film makers during the 1940’s and 1950’s for the on-location shooting of Westerns. Actors and film crews would stay at the hotel during filming.
Day 11 – Gallup to Winslow, AZ
Ride out of Gallup today on Route 66 and stop at the Petrified Forest. We then work our way to Stand on a Corner in Winslow, Arizona where we arrive early today with plenty of time for pictures on the famous Rt 66 corner with you and your classic car. This is a relaxing day with an early arrival and an iconic destination.
Day 12 – Winslow, AZ to Grand Canyon National Park
Next we drive down the main drag on Rt 66 in our Convertibles with the top down through Flagstaff. Then, we stay on top of the Canyon and watch the sunset the first night. The Grand Canyon. “That’s one big hole!”, enough said. Seeing the sun set over the Grand canyon is one of the things that everyone should see once in a lifetime. We have dinner right on the rim of the Canyon. At night, we can walk back over to the rim under the stars.
Day 13 – Grand Canyon National Park to Williams, AZ
What is different about Ride Free Chicago to LA Route: We stay at the top of the Grand Canyon for the sunset, unlike most tours who only stay at the bottom. We also spend a whole day at the Grand Canyon the next day, then ride to the bottom so we have more time on an amazing part of Route 66 the next day.
For those that want to ride more, we have an amazing ride set up for the day.
Who is up for a helicopter ride across the canyon after watching the sunrise?
Hike down a trail the next am. into the Grand Canyon. Ride the donkeys down the trail into the canyon? Just relax enjoy the sites and history.
Check out the Watchtower. Lots of great things to see. We get a full day in The Grand Canyon. When we are done here, we start heading back down the mountain and stop if you want for a helicopter or plane ride into the Canyon. Or maybe an old train ride? We then work our way down the hill after an amazing day to Williams for dinner and a night on the little town. Or sleep. Ready to hit the road the next am for an amazing day.
Day 14 – Williams to Laughlin, NV
An amazing Old RT 66 day! All the RT 66 shopping you could think of. We will be on the forgotten RT 66 a lot of the day. Grand Canyon Caverns, Peach Springs, Kingman…Towards the end of the day we will work our way on an incredible slow winding road to the old mining town of Oatman. Wild burros, real old 49er gold miners with real Colt 45s on their hips to protect their gold. A forgotten town. Not much has changed here the past 100 years. It is almost unbelievable that is winding mountain road was the main East West road until 1953 when Rt 66 was re routed. Time has held still since then in Oatman.
Laughlin is a little Gambling town on the way to Vegas on the Colorado River. Let’s get you ready for the Big Time tomorrow.
Ribeye Steak tonight!
Day 15 – Laughlin, NV to Las Vegas, NV
An early morning ride out beats the heat, and gets us to Vegas early for a full day…. Plenty of time relax in your Vegas room and get cleaned up before hitting the Vegas Strip. Of course we get a picture in from of the famous Las Vegas sign when we ride in town down the strip in our cars.
Or, instead of just Vegas lounging, we have some great rides out from Vegas if you want some more cruising our Mustangs in Las Vegas. Like Red Rock Canyon and some other stops.
But first the Hoover Dam!
Vegas – Pools, shows, fun. We will have most of the day to explore Vegas, and the whole relaxed evening.
Day 16 – Las Vegas, NV to Big Bear Lake (or Victorville), CA
We follow the original path of Old Route 66 where we explore the amazing Mojave desert. When we do the Big Bear Option we climb into the cool Alpine town of Big Bear Lake at the end of the day.
Day 17 – Big Bear Lake (or Victorville) to Santa Monica Pier! 113 miles
It is not over yet! We ride the Rim of The World. An incredible drive on the top of a mountain range, with the clouds below. One of our most amazing rides. Then we drop into LA, freeways, civilization. We make it through all the way to the end of Route 66! The Santa Monica Pier. … let’s keep the Ride Free tradition of ending the tour by putting our feet into the cold Pacific! We turn the cars in at the end of the day. A victory dinner tonight!
Day 18 – Los Angeles Departure
We say our goodbyes, and plan for our next adventure. There is so much more to see in the USA in the future.
A shuttle will take you to the LAX.
We meet after lunchtime at the hotel and talk about our upcoming adventure on the Mother Road of America, Route 66 Chicago to LA.
We also do an orientation with the classic cars to familiarize ourselves with the upcoming adventure on Route 66 in cars like Mustang Convertibles.
Then we go out for dinner after checking out the beginning of Route 66 in downtown Chicago to discuss our big adventure!
Day 2 – Chicago to Springfield, Illinois
Let’s get in our cars and drive on Route 66!
We settle into our car rentals , and aim for California. This is our first night on the road.
See icons such as the “Gemini Giant”, “Rocket Man”, “Old Log Cabin”, the old “Marathon Oil Station”. We also stop at the RT 66 Museum in Joliet.
That afternoon we arrive to Springfield and stay at a nice local hotel in historic downtown where we can visit the amazing Lincoln Museum if we have time before having dinner at a local restaurant and celebrate our first night on the road.
Day 3 – Springfield, Illinois to Saint Louis
Riding Rt 66. Exploring St. Louis. The Gateway Arch welcomes travelers heading East or West. Maybe a blues bar tonight?
Before we get to Saint Louis, we drive out cars with the top down to the historic Chain of Rocks Bridge. We will walk out on the old bridge!
Day 4 – St Louis to Lebanon, MO
Riding Rt 66 through neat little towns. We have really fallen into sync with our rides now.. Americana. How about some great American BBQ? We get a picture with the worlds largest Rocking Chair. Devils Elbow is amazing. This is small town America. At a glance it does not seem like much has changed. We hang out with the locals tonight and relax under the stars under some neon light of a vintage Rt 66 Motel in the countryside.
Day 5 – Lebanon to Tulsa, OK 233 miles
Great section of RT 66 with all the Googie Architecture. A really great ride. Great old diners. A really nice driving day. This is one of the longest days, but a great day.
This is RT 66! We stop and meet some very interesting people along the ride today, and ride over a famous RT 66 Bridge in our cars. Then we go stop at a great little motorcycle museum along the way that has a great history of Rt 66.
Day 6 – Tulsa to Clinton OK 191 miles
Today is a really nice cruise through the countryside. So many great little signs and remnants of the hay days of this great road to see. We end the day with the Oklahoma Route 66 Museum where we can travel in time back to the glory days of Rt 66.
Day 7 – Clinton to Amarillo, TX
In the morning after a short ride we visit the Elk City Rt 66 Museum. I could spend a day at this one. It is absolutely amazing. The farming history, Wild West History, and every aspect of old America. Welcome to Texas! The panhandle of Texas. Big Texan Steakhouse for dinner? Everything is bigger in Texas. You will know you are on old Rt 66 today. It will feel like a throwback to what it was like to travel Rt 66 on the road in years past.
DAY 8 – Amarillo to Santa Fe, NM
Cadillac Ranch is a Route 66 stop we must do. Who has ever spray painted a vintage Cadillac on Rt 66 before? Let me ask you again in the future… Midpoint of Rt 66 at the Midpoint Café! Amazing day of vintage hotels and neon signs like The Blue Swallow and others. Welcome to Santa Fe. Art galleries, great restaurants, great walking around…. This is really an amazing Southwest city to spend time in. We discover the rich history and culture of Santa Fe after a big day riding Route 66 in our cars.
Day 9 – Santa Fe Layover
Day 10 – Santa Fe to Gallup
We follow the Route 66 path, and end at the little town of Gallup, at the Rancho Hotel.
The historic El Rancho Hotel and Motel has hosted a numerous array of movie stars including John Wayne, Ronald Reagan, Humphrey Bogart, Spencer Tracy, Katharine Hepburn, Joan Crawford, Kirk Douglas, Doris Day, Gregory Peck, and Burt Lancaster. The rugged terrain surrounding Gallup was popular with Hollywood film makers during the 1940’s and 1950’s for the on-location shooting of Westerns. Actors and film crews would stay at the hotel during filming.
Day 11 – Gallup to Winslow, AZ
Ride out of Gallup today on Route 66 and stop at the Petrified Forest. We then work our way to Stand on a Corner in Winslow, Arizona where we arrive early today with plenty of time for pictures on the famous Rt 66 corner with you and your classic car. This is a relaxing day with an early arrival and an iconic destination.
Day 12 - Winslow, AZ to Grand Canyon National Park
Next we drive down the main drag on Rt 66 in our Convertibles with the top down through Flagstaff. Then, we stay on top of the Canyon and watch the sunset the first night. The Grand Canyon. “That’s one big hole!”, enough said. Seeing the sun set over the Grand canyon is one of the things that everyone should see once in a lifetime. We have dinner right on the rim of the Canyon. At night, we can walk back over to the rim under the stars.
Day 13 – Grand Canyon National Park to Williams, AZ
What is different about Ride Free Chicago to LA Route: We stay at the top of the Grand Canyon for the sunset, unlike most tours who only stay at the bottom. We also spend a whole day at the Grand Canyon the next day, then ride to the bottom so we have more time on an amazing part of Route 66 the next day.
For those that want to ride more, we have an amazing ride set up for the day.
Who is up for a helicopter ride across the canyon after watching the sunrise?
Hike down a trail the next am. into the Grand Canyon. Ride the donkeys down the trail into the canyon? Just relax enjoy the sites and history.
Check out the Watchtower. Lots of great things to see. We get a full day in The Grand Canyon. When we are done here, we start heading back down the mountain and stop if you want for a helicopter or plane ride into the Canyon. Or maybe an old train ride? We then work our way down the hill after an amazing day to Williams for dinner and a night on the little town. Or sleep. Ready to hit the road the next am for an amazing day.
Day 14 – Williams to Laughlin, NV
An amazing Old RT 66 day! All the RT 66 shopping you could think of. We will be on the forgotten RT 66 a lot of the day. Grand Canyon Caverns, Peach Springs, Kingman…Towards the end of the day we will work our way on an incredible slow winding road to the old mining town of Oatman. Wild burros, real old 49er gold miners with real Colt 45s on their hips to protect their gold. A forgotten town. Not much has changed here the past 100 years. It is almost unbelievable that is winding mountain road was the main East West road until 1953 when Rt 66 was re routed. Time has held still since then in Oatman.
Laughlin is a little Gambling town on the way to Vegas on the Colorado River. Let’s get you ready for the Big Time tomorrow.
Ribeye Steak tonight!
Day 15 – Laughlin, NV to Las Vegas, NV
An early morning ride out beats the heat, and gets us to Vegas early for a full day…. Plenty of time relax in your Vegas room and get cleaned up before hitting the Vegas Strip. Of course we get a picture in from of the famous Las Vegas sign when we ride in town down the strip in our cars.
Or, instead of just Vegas lounging, we have some great rides out from Vegas if you want some more cruising our Mustangs in Las Vegas. Like Red Rock Canyon and some other stops.
But first the Hoover Dam!
Vegas – Pools, shows, fun. We will have most of the day to explore Vegas, and the whole relaxed evening.
Day 16 – Las Vegas Layover
Day 17 – Las Vegas, NV to Big Bear Lake (or Victorville), CA
We follow the original path of Old Route 66 where we explore the amazing Mojave desert.
Day 18 – Big Bear Lake (or Victorville) to Santa Monica Pier! 113 miles
It is not over yet! We ride the Rim of The World. An incredible drive on the top of a mountain range, with the clouds below. One of our most amazing rides. Then we drop into LA, freeways, civilization. We make it through all the way to the end of Route 66! The Santa Monica Pier. … let’s keep the Ride Free tradition of ending the tour by putting our feet into the cold Pacific! We turn the cars in at the end of the day. A victory dinner tonight!
Day 19 – Los Angeles Departure
We say our goodbyes, and plan for our next adventure. There is so much more to see in the USA in the future.
A shuttle will take you to the LAX.
Classic Car Route 66 Chicago to LA Tour and Rental
Route 66 Chicago to LA Guided Classic Car Tour and Rental – 17 days
Drive Chicago to LA in a Classic car on Route 66 the Mother Road of America. Chicago, Route 66, The Grand Canyon, Las Vegas, Los Angeles
A once in a life time journey and opportunity not many have ever had the chance to do since the 1950’s! Chicago to LA Classic Car Route and Itinerary Classic Car Pricing for this trip below
Rent a Classic or Late Model Muscle Car, OR BRING YOUR OWN CLASSIC CAR
Our brother company, Sakowski Motors Classic Cars has been making classic cars reliable for 30 years.
We can work with you and your local shops to prep your car for the trip. Classic Car Repair Consulting | Sakowski Motors
Then we can ship your car from your home to the start of the trip, then ship it back to you at the end of your trip. Classic Car Shipping | Sakowski Motors
17 Day 16 Night Chicago to LA Classic Car Tour and Rental – Guided Tour with Support
-like 16 Day trip, but we add a layover in Santa Fe to rest and relax
– This is the best trip by far, does not feel like a mission, like other trips
Cost 15 Day 14 night Classic Car Tour Chicago to LA – TAX INCLUDED
$4288 – Per person with 4 people, 1 car, 2 rooms
$5670– Per person with 3 people, 1 car, 2 rooms
$7525 – Per person with 2 people, 1 car, 1 room
Cost 16 Day 15 night Classic Car Tour Chicago to LA – TAX INCLUDED
$4563 – Per person with 4 people, 1 car, 2 rooms
$6083 – Per person with 3 people, 1 car, 2 rooms
$8000 – Per person with 2 people, 1 car, 1 room
Cost 17 Day 16 night Classic Car Tour Chicago to LA – TAX INCLUDED
$4838 – Per person with 4 people, 1 car, 2 rooms
$6450 – Per person with 3 people, 1 car, 2 rooms
$8475 – Per person with 2 people, 1 car, 1 room
Self Guided Classic Car Tour Option: car, route, attractions, hotels, GPS CONTACT for Self Drive packages and rates
15 Day Tours start same start date as the 17 day Tours, just end 2 days earlier, 16 Day Tours end 1 day earlier
2021 Chicago to LA Classic Car Tour – Start Dates – Guided Classic Car Tours
May 5 –June 9 –July 7 –Aug 4 – Sept 1 –Oct 2 – Nov 2
May 1 – May 15, 2021 – 17 Day – ROUTE 66 CHICAGO TO LA
May 22 – June 6, 2021 – 17 Day – ROUTE 66 CHICAGO TO LA
September 10 – 25, 2021 – 17 Day – ROUTE 66 CHICAGO TO LA
Sept 17 – Oct 3, 2021- 17 Day – ROUTE 66 CHICAGO TO LA CLASSIC CAR TOUR – Eastbound
Oct 2 – 17, 2021 – 17 Day- ROUTE 66 CHICAGO TO LA CLASSIC CAR TOUR – Westbound
2022 Chicago to LA Classic Car Tour – Start Dates – Guided Classic Car Tours
May 5 –June 9 –July 7 –Aug 4 – Sept 1 –Oct 2 – Nov 2
May 1 – May 15, 2022 – 17 Day – ROUTE 66 CHICAGO TO LA
May 22 – June 6, 2022 – 17 Day – ROUTE 66 CHICAGO TO LA
September 10 – 25, 2022 – 17 Day – ROUTE 66 CHICAGO TO LA
Sept 17 – Oct 3, 2022- 17 Day – ROUTE 66 CHICAGO TO LA CLASSIC CAR TOUR – Eastbound
Oct 2 – 17, 2022 – 17 Day- ROUTE 66 CHICAGO TO LA CLASSIC CAR TOUR – Westbound
2023 Chicago to LA Classic Car Tour – Start Dates – Guided Classic Car Tours
May 5 –June 9 –July 7 –Aug 4 – Sept 1 –Oct 2 – Nov 2
May 1 – May 15, 2023 – 17 Day – ROUTE 66 CHICAGO TO LA
May 22 – June 6, 2023 – 17 Day – ROUTE 66 CHICAGO TO LA
September 10 – 25, 2023 – 17 Day – ROUTE 66 CHICAGO TO LA
Sept 17 – Oct 3, 2023- 17 Day – ROUTE 66 CHICAGO TO LA CLASSIC CAR TOUR – Eastbound
Oct 2 – 17, 2023 – 17 Day- ROUTE 66 CHICAGO TO LA CLASSIC CAR TOUR – Westbound
Our RideFree experience was an adventure of epic proportions. With the guidance of Wil and strategic planning, we managed to do a self-guided tour from LA to Yosemite National park,... read more 
