Route 66 Chicago to LA Harley Davidson Motorcycle Tour

Ride Historic Route 66 from Chicago to LA on a 15 day guided motorcycle tour USA  down the Mother Road of America on a Harley Davidson motorcycle.    Explore old Rt 66, The Grand Canyon, Las Vegas,  and more.  Ride Free has smaller size groups with more flexible and personal tours than the huge companies.
Or ride a Harley for a 10 day tour from Albuquerque to LA on Route 66, or 12 day Motorcycle Tour Chicago to Las Vegas.  For the ultimate Route 66 Harley-Davidson Motorcycle Rt 66 Tour make it a 17 day so you have time to really explore all the history along Rt 66.

Click Here for PICTURES and VIDEOS  These will show what Ride Free  is truly all about.

Click Here for Pictures from Route 66 Guided Motorcycle Tour 2014     , 2013 Trip

But what really makes a Ride Free Adventure is The Team, check out our crew.  Our love for being on the road on a motorcycle adventure with great people from around the world is what it is all about for us.

route 66 harley motorcycle tour

See the Route 66 Chicago to Las Vegas with Grand Canyon 15 Day Option

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.

What is different about Ride Free Chicago to LA Route:  We typically run smaller more personalized tours than other Chicago to LA Motorcycle Tour Companies. We stay at the top of the Grand Canyon for the sunset and sunrise, unlike most tours who only stay only at the bottom.  We also spend a whole day at the Grand Canyon the next day giving time for a helicopter ride or donkey ride, then ride to the bottom so we have more time on an amazing part of Route 66 the next day.  We also get to Vegas early so you have a full afternoon and relaxed evening in Las Vegas.

Guided Tour – Per Person                        10 Day 9 Night                     13 Day 12 Night         15 D 14 Ni                  16D 15N Ultra  17D 15N Ultimate
2 People – 1 Bike – 1 Room  $3340 + $213 $4119 + $298  $4299  $4912  $5525
2 People – 2 Bikes – 1 Room  $4200 + $425 $5238 + $595  $6990  $7560  $8130
1 Person – 1 Bike – 1 Room  $4988 + $425 $6452  $7995  $8873  $9751

Ride Free Chicago to LA Rt 66 Motorcycle Tour HAS SMALLER GROUP SIZES THAN THE HUGE  TOURS, unless you request a large group.

Self Drive Tour Per Person 10 Day 9 Night 13 Day 12 Night 15 Day 14 Night 16 Day 15 Night Ultra 17D 16N Ultimate
Self Drive 2 Riders 1 Room  $2311 + $425  $3145 + $595 $3700 + $595
$3978 + $595 one way fee  $4256 + $595 one way fee
Self Drive 1 Rider 1 Room $3100 + $425  $4201 + $595 $4925 + $595
$5291 + $595 one way fee  $5657 + $595 one way
July 24 –  Aug 7, 2014 – Route 66 CHICAGO TO LA Motorcycle Tour  with Grand Canyon and Vegas
Aug 7  - 21, 2014 – Route 66 CHICAGO TO LA Motorcycle Tour  with Grand Canyon and Vegas
Aug 14 – 28, 2013- Route 66 CHICAGO TO LA Motorcycle Tour with Grand Canyon and Vegas
Aug 21  -  Sept 4, 2014 – Route 66 CHICAGO TO LA Motorcycle Tour  with Grand Canyon and Vegas
Sept 11  -  25, 2014 – Route 66 CHICAGO TO LA Motorcycle Tour  with Grand Canyon and Vegas
Sept 18  -  Oct 2, 2014 – Route 66 CHICAGO TO LA Motorcycle Tour  with Grand Canyon and Vegas
Sept 25  -  Oct 9, 2014 – Route 66 CHICAGO TO LA Motorcycle Tour  with Grand Canyon and Vegas

Contact Us    Tour Schedule with More Dates

 

                                                                                                 

RT 66 Chicago to LA  All Inclusive – $595 return fee included at no extra charge to you (Chicago starts only),  Breakfast, Gas, Tour Guides, Support Vehicle, National Park Fees, Motorcycle, Lodging.    Not included: Optional Helicopter ride at the Grand Canyon, insurance options, lunch and dinners, tour guide gratuity.

#Lunch and Dinner not included in RT 66 Tours.   #Food plan available.    We still arrange all meals and give options,  and you can eat with the group or separate.  It is up to you.

Self Guided / Drive - Motorcycle, Route, Lodging, support – Add $595 return fee for Self Guided Tours
2013 Tours are being offered in May, June, July, August,  September, and October
Contact me for desired dates. We will be setting the exact dates per request. Contact Us Here for Dates
Ride with a smaller more intimate group than most RT 66 Tours out there, or we can take your custom large private group.

ITINERARY BELOW

11 Day 10 night is the same as Option 1 / Traditional but take out: Blommington, Durango, Williams, Big Bear), tour over after dinner day 10

Option 1 – 15 Day 14 Night – Traditional  Classic Route 66 Motorcycle Tour
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.

Option 2 – 16 Day 15 Night – Ultra Route 66 Motorcycle Tour – or 17 day Ultimate Explorer
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.
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 Motorcycle Tour
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 – Albuquerque to Los Angeles Motorcycle Tour
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 Albuquerque / Santa Fe  to Los Angeles on Route 66.

 


OPTION 1:  15 DAY 14 NIGHT – Traditional Classic Route 66 Motorcycle Tour

Day 1 Arrive in Chicago
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 bikes to familiarize ourselves with the upcoming adventure and our Harley Davidsons.
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- 185 miles


Let’s hop on our Harley Davidsons and ride Route 66!
We settle into our bikes, 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 to learn about the history of Rt 66.

That afternoon we arrive to Springfield on our Harley Davidsons and stay at a nice local hotel in historic downtown where we can visit the amazing Lincoln Museum before having dinner at a local restaurant and celebrate our first night on the road.

 

 

 

 

 

 

 

 

 

 

 

 

 

 

Day 3 – Springfield, Illinois to Saint Loius, MO 175miles


 

 

 

 

 

 

 

 

 

 

 

 Riding Rt 66. Exploring St. Louis. The Gateway Arch welcomes travelers heading East or West. The famous Budweiser Brewery. Maybe a blues bar tonight?  There is so much to discover and explore on the motorcycle adventure across the Mother Road of America, Route 66!

Before we get to Saint Louis, we ride our Harley-Davidson motorcycles to the historic Chain of Rocks Bridge.  We will walk out on the old bridge!

Day 4St Louis to Springfield, Missouri – 216 miles

Riding our motorcycles on Rt 66 through neat little towns, we have really fallen into synch with our Harley Davidsons.  Americana. Devils Elbow is amazing.

Day 5Springfield, Missouri to Oklahoma City – 285 miles
A great section of RT 66 with all the Googie Architecture. A really great motorcycle ride on old pavement of the Mother Road.  We visit some great old diners.
This is RT 66!

Day 6Oklahoma City to Amarillo, Texas – 259 miles

 

 

 

 

 

 

 

 

 

 

 

 

 

 

Elk Cit Rt 66 Museum. Welcome to Texas! The panhandle of Texas. Big Texan Steakhouse for dinner?   Everything is bigger in Texas.  Let’s live a little old Route 66 today on our motorcycle and tonight.  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.  After riding your motorcycle all day you will be ready for a big steak dinner.

Day 7Amarillo to Santa Fe, New Mexico – 279 miles

 

 

 

 

 

 

 

 

 

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…   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 motorbike day riding Route 66 on our Harley Davidsons.

DAY 8Santa Fe  to Gallup – 191 miles plus excursions
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 9 Gallup to Grand Canyon National Park South Rim – 283 miles
First, we will stand on a corner in Winslow, Arizona.
 

Next we ride down the main drag on Rt 66 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 10Grand Canyon South Rim to Williams, AZ – 51 miles – Almost Full Day At Grand Canyon! – Or go for an amazing ride.
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 11 Williams to Laughlin, NV – 190 miles

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! 

harley davidson las vegas motorcycle tourDay 12Laughlin, NV to Las Vegas, NV – 97 miles – Almost Full Day in Vegas!


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 Harley-Davidsons!
Or, instead of just Vegas lounging, we have some great rides out from Vegas if you want some more riding.  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 13Las Vegas, NV to Victorville, CA – 190 miles

( or we can do Big Bear Lake Option if want, see Ultra Tour below )
We follow the original path of Old Route 66 where we can, and explore the amazing Mojave desert. 

Day 14 Victorville  / Big Bear to Santa Monica Pier! – 100 miles. plus exploring and Malibu Coast Ride!

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 bikes in at the end of the day.

A victory dinner tonight!

 

 

 

 

 

 

 

 

 

 

 

 

Day 15Los 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.

 

ROUTE 66 ULTRA MOUNTAIN TOUR ITINERARY 16 DAY 15 NIGHT


 

Day 1 Arrive in Chicago
We meet after lunchtime at the hotel. We also do an orientation with the bikes.

Then we go out for dinner to discuss our big adventure!

Day 2Chicago to Springfield, Illinois- 185 miles
Short Tour out of Chicago. Let’s go!

We settle into our bikes, 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.

Day 3 – Springfield, Illinois to Saint Louis- 175 miles
Breakfast at the “Dixie Truckers Home”. Riding Rt 66. Exploring St. Louis. The Gateway Arch welcomes travelers heading East or West. The famous Budweiser Brewery. Maybe a blues bar tonight?

Day 4 – St Louis to Springfield, Missouri - 216 miles

Riding our motorcycles on Rt 66 through neat little towns, we have really fallen into synch with our Harley Davidsons.  Americana. Devils Elbow is amazing.

Day 5 – Springfield, Missouri to Oklahoma City - 285 miles
A great section of RT 66 with all the Googie Architecture. A really great motorcycle ride on old pavement of the Mother Road.  We visit some great old diners.
This is RT 66!

 

Day 6 Oklahoma City to Amarillo, Texas – 259 miles
Elk Cit Rt 66 Museum. Welcome to Texas! The panhandle of Texas. Big Texan Steakhouse for dinner?

Day 7 Amarillo to Santa Fe, New Mexico - 279 miles
Cadillac Ranch. Welcome to Santa Fe. Art galleries, great restaurants, great walking around…. This is really an amazing Southwest city to spend time in.

option1 – 2nd layover here, or Durango trip the next day.

option2 – Just one day here.

Day 8 Santa Fe to Durango, Colorado – 241 miles
We take a break today from the straights of Route 66, and climb into the mountains of Colorado. Winding mountain roads, beautiful scenery. Welcome to an old cow town. The next am reconnecting with Route 66.

DAY 9 Durango to Gallup, New Mexico – 180 miles
We 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 10 Gallup to Grand Canyon National Park – 283 miles
We stay on top of the Canyon and watch the sunset the first night. The Grand Canyon. “That’s one big hole!”, enough said.

Day 11 Grand Canyon to Williams, AZ – 51 miles
Hike down a trail the next am. into the Grand Canyon. Ride the donkeys down the trail into the canyon?

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 Western town. Or sleep. Ready to hit the road the next am for an amazing day.

Day 12Williams to Laughlin, NV – 190 miles
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 and Mico Brewery tonight!

Day 13 Laughlin, NV to Las Vegas, NV – 97 miles
An early morning ride out beats the heat, and gets us to Vegas early for a full day….

But first the Hoover Dam!
Vegas – Pools, shows, fun. We will have most of the day to explore Vegas, and the whole evening.

Day 14Las Vegas, NV to Big Bear Lake, CA – 224 miles
We take a little Rt 66 excursion up into the amazing San Bernardino mountains. A last long hard ride through the desert, we are covered in desert dust. Our bikes are covered in road grime. They and we look and feel like we really did something. We have. Then a climb up into the twisty mountains brings us to an awaiting pool in the cool alpine town of Big Bear Lake.

Day 15 Big Bear Lake to Santa Monica Pier! – 113 miles
It is not over yet! We ride the Rim of The World. An incredible ride 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. 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 bikes in at the end of the day.

A victory dinner tonight!

DAY 16 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.