Loading... Please wait

THE BEST VACATION EVER.
– Bill and Judy Gore, Australia
View Reviews

ROUTE 66 GUIDED MOTORCYCLE TOUR

ROUTE 66 TOUR INFO
WHAT’S INCLUDED
MOTORCYCLE CHOICES
WHERE WE STAY
GUIDED TOUR FAQ’S
BOOK

Why Choose Our Guided Motorcycle Tour?

Personal Care

Talk to the owner anytime
We care about your dream coming true
Small family business, not corporate
Every person is important to us
READ MORE

No Mass Production

Small group
Stay in small local hotels
Go to small local stops and restaurants
Shorter riding days to experience more
READ MORE

Real American Experience

American tour guides and company
Foreigners can't give the same
Learn what a real American ride is
Let us share our country with you
READ MORE

15 DAY ROUTE 66 TOUR

16 DAY ROUTE 66 TOUR

17 DAY ROUTE 66 TOUR

18 DAY ROUTE 66 TOUR

19 DAY

ROUTE 66 TOUR

19 DAY ROUTE 66 TOUR VIA MILWAUKEE

10 DAY ROUTE 66 TOUR Chicago to Albuquerque

9 DAY ROUTE 66 TOUR Albuquerque to LA

DEALS AND SPECIALS

EARLY BOOKING DISCOUNT

PASSENGERS RIDE FREE

DEALS AND SPECIALS

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

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

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

Andrew H
10/26/2019

View All Reviews

Sturgis Tour

"The Greatest Trip of my life!"

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

310-978-9558

ROUTE 66 TOUR INFORMATION

Route 66 Guided Motorcycle Tour Highlights

Route 66 Motorcycle Tour. Ride Historic Route 66 from Chicago to LA on a 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 with the Oldest Motorcycle Tour Company in the USA. Fully Insured.

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 Aug 2014   , 2013 Trip
Click Here   For 850 Pictures of the entire Route 66 Motorcycle Tour

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.

What is different about Ride Free Chicago to LA Motorcycle Tour 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.

RT 66 Chicago to LA All Inclusive – GUIDED TOUR FAQ’S FREQUENTLY ASKED QUESTIONS
Motorcycle return fee included at no extra charge to you (Chicago starts only), some 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.
Since we don’t normally stay in the generic chain hotels that have the small continental breakfast like most tour companies, but smaller more unique accommodations when possible, a breakfast is not included all mornings.

Self Guided / Drive – Motorcycle, Route, Lodging, Daily Itinerary, Support

ROUTE 66 MOTORCYCLE TOUR OPTIONS / DESCRIPTIONS

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 highly suggest at least our 16 or 17 Day Rt 66 Option, itinerary below. The days are long with so much to see, the 15 day is much more grueling than you would expect. Do the 16 day and we divide the longest 15 tour day in half. So much better, it is unbelievable till you do it. Trust me. Believe me now or later…

We are the OLDEST MOTORCYCLE TOUR COMPANY IN THE USA, since 1993. We are not the largest, fanciest, or most corporate tour company; we are a tight group of friends who love taking you on tour and making new friends from all over the world. Fully Insured Tour Company.
The Team CONTACT US Testimonials Pictures Mission

15 DAY – Route 66 Guided Motorcycle Tour

Guided Tours

DATES | PRICING | BOOKING

Self Drive Tours

DATES | PRICING | BOOKING

View Map

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 a Rt 66 Museum in Pontiac to learn about Route 66 and the people who make America great. That afternoon we arrive to Springfield on our Harley Davidsons and stay at a nice local hotel in historic downtown where we can have dinner at a local restaurant and celebrate our first night on the road.

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

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 onto an old section of Route 66 that is all red bricks. Then to the historic Chain of Rocks Bridge. We will walk out on the old bridge over the mighty Mississippi River.

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. We have some great authenic BBQ for lunch, and see the World’s Largest Rocking Chair. We get to see the real America that is still here, far far away from the big cities. Then we ride down a deserted twisty old part of Route 66 on our motorcycles to Devil’s Elbow.

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. Gary’s Gay Parita and the old Rt 66 Rainbow Bridge are some highlights. We visit some great old diners. This is Rt 66 on a Harley!

Day 6 – Oklahoma City to Amarillo, Texas 259 miles

The Elk Cit Rt 66 Museum is full of American history from farming to the Wild West. Welcome to 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 7 – Amarillo to Santa Fe, New Mexico – 176 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… We make it to the Midpoint of Rt 66! Then 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 8 – Santa Fe to Gallup 191 miles

We follow the Route 66 path, and end at the little town of Gallup, at the Rancho Hotel. But first let’s ride our Harleys to Maggie’s Diner, where the big fight happened in Wild Hogs! Then to Old Town Albuquerque. 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 10 – Grand Canyon South Rim to Williams, AZ 283 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 an old part of RT 66 a lot of the day. We ride our Harley motorcycles through old towns, some great shopping spots with old stores and memoralbilia. 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 12 – Laughlin, 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 13 – Las Vegas, NV to Big Bear Lake (or Victorville), CA 190 miles

( or we can do Big Bear Lake Option if would like) We follow the original path of Old Route 66 where we can, and explore the amazing Mojave desert. Or if you have had enough desert at this point, we will leave the hot straight desert behind and climb high above the clouds through the cool crisp mountain air on amazing twisty mountain roads to the alpine lake of Big Bear on our motorcycles.

Day 14 – Big Bear Lake (or Victorville) to Santa Monica Pier! 100 miles or add more twisties option

You think the trip is about done? No way. Some of the best motorcycling riding is today. We ride through the California mountains on our Harley or Indian motorcycles carving our way one perfect motorcycle curve after another. Before we drop down into civilization we have a great stop on top of the mountain with amazing views towards our destination. Then it is time to head over the famous Cajon Pass, 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 bikes in at the end of the day. A victory dinner tonight.

Day 15 – 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.

×

16 DAY – Route 66 Guided Motorcycle Tour

Guided Tours

DATES | PRICING | BOOKING

Self Drive Tours

DATES | PRICING | BOOKING

View Map

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 2 – Chicago to Springfield, Illinois –185 miles

Start 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

Today we ride over the famous old red brick section of Rt 66. It is a tucked away little gem. Amazing day riding Rt 66. Exploring St. Louis. Then we ride our bikes to the famous Rt 66 Chain of Rocks Bridge that goes over the mighty Mississippi River. The Gateway Arch welcomes travelers heading East or West. The famous Budweiser Brewery. Maybe a blues bar tonight?

Day 4 – St Louis to Lebanon, MO 153 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 – Lebanon to Tulsa, OK 233 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 – Tulsa to Clinton OK 191 miles

Elk Cit Rt 66 Museum. Welcome to Texas! The panhandle of Texas. Big Texan Steakhouse for dinner?

Day 7 – Clinton to Amarillo, TX – 176 miles

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.

DAY 8 – Amarillo to Santa Fe, NM 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 day riding Route 66 on our Harley Davidson.
Santa Fe, NM – Layover on 17 Day Ultimate Tour – Relax and enjoy this great town. We can take short nice ride up into the beautiful mountains today. Or just enjoy a full day of rest and fun. If you can do the 17 day, I highly recommend it.

Day 9 – Santa Fe to Gallup 199 miles

We start the day riding the curvy hills to Maggie’s Diner where the big showdown was in “Wild Hogs”. Then lunch in Old Town Albuquerque. Next 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 10 – Gallup to Grand Canyon National Park 283 miles

We stand on a corner in Winslow, Arizona. 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.

Day 12 – Williams to Laughlin, NV 190 miles

The quintessential Western 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 for an early lunch….. But first the Hoover Dam! Vegas – Pools, shows, fun. We will have a lot of the day to explore Vegas, and the whole evening.

Day 14 – Las Vegas, NV to Big Bear Lake (or Victorville), CA 224 miles

We take a little Rt 66 excursion up into the amazing San Bernadino 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 (or Victorville) 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 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 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.

×

17 DAY – Route 66 Guided Motorcycle Tour

Guided Tours

DATES | PRICING | BOOKING

Self Drive Tours

DATES | PRICING | BOOKING

View Map

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 2 – Chicago to Springfield, Illinois –185 miles

Start 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

Today we ride over the famous old red brick section of Rt 66. It is a tucked away little gem. Amazing day riding Rt 66. Exploring St. Louis. Then we ride our bikes to the famous Rt 66 Chain of Rocks Bridge that goes over the mighty Mississippi River. The Gateway Arch welcomes travelers heading East or West. The famous Budweiser Brewery. Maybe a blues bar tonight?

Day 4 – St Louis to Lebanon, MO 153 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 – Lebanon to Tulsa, OK 233 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 – Tulsa to Clinton OK 191 miles

Elk Cit Rt 66 Museum. Welcome to Texas! The panhandle of Texas. Big Texan Steakhouse for dinner?

Day 7 – Clinton to Amarillo, TX – 176 miles

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.

DAY 8 – Amarillo to Santa Fe, NM 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 day riding Route 66 on our Harley Davidson.

Day 9 – Santa Fe, NM – Layover on 17 Day Ultimate Tour

Relax and enjoy this great town. We can take short nice ride up into the beautiful mountains today. Or just enjoy a full day of rest and fun.

Day 10 – Santa Fe to Gallup 199 miles

We start the day riding the curvy hills to Maggie’s Diner where the big showdown was in “Wild Hogs”. Then lunch in Old Town Albuquerque. Next 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 283 miles

We stand on a corner in Winslow, Arizona. 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 12 – 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.

Day 13 – Williams to Laughlin, NV 190 miles

The quintessential Western 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 14 – Laughlin, NV to Las Vegas, NV 97 miles

An early morning ride out beats the heat, and gets us to Vegas for an early lunch….. But first the Hoover Dam! Vegas – Pools, shows, fun. We will have a lot of the day to explore Vegas, and the whole evening.

Day 15 – Las Vegas, NV to Big Bear Lake (or Victorville), CA 224 miles

We take a little Rt 66 excursion up into the amazing San Bernadino 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 16 – 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 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 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 bikes in at the end of the day. A victory dinner 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. A shuttle will take you to the LAX.

×

18 DAY – Route 66 Guided Motorcycle Tour

Guided Tours

DATES | PRICING | BOOKING

Self Drive Tours

DATES | PRICING | BOOKING

View Map

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 2 – Chicago to Springfield, Illinois –185 miles

Start 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

Today we ride over the famous old red brick section of Rt 66. It is a tucked away little gem. Amazing day riding Rt 66. Exploring St. Louis. Then we ride our bikes to the famous Rt 66 Chain of Rocks Bridge that goes over the mighty Mississippi River. The Gateway Arch welcomes travelers heading East or West. The famous Budweiser Brewery. Maybe a blues bar tonight?

Day 4 – St Louis to Lebanon, MO 153 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 – Lebanon to Tulsa, OK 233 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 – Tulsa to Clinton OK 191 miles

Elk Cit Rt 66 Museum. Welcome to Texas! The panhandle of Texas. Big Texan Steakhouse for dinner?

Day 7 – Clinton to Amarillo, TX – 176 miles

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.

DAY 8 – Amarillo to Santa Fe, NM 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 day riding Route 66 on our Harley Davidson.

Day 9 – Santa Fe, NM – Layover

Relax and enjoy this great town. We can take short nice ride up into the beautiful mountains today. Or just enjoy a full day of rest and fun.

Day 10 – Santa Fe to Gallup 199 miles

We start the day riding the curvy hills to Maggie’s Diner where the big showdown was in “Wild Hogs”. Then lunch in Old Town Albuquerque. Next 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 motorcycle. This is a relaxing day with an early arrival and an iconic destination.

Day 12 – Winslow, AZ to Grand Canyon National Park

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 13 – 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.

Day 14 – Williams to Laughlin, NV 190 miles

The quintessential Western 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 15 – Laughlin, NV to Las Vegas, NV 97 miles

An early morning ride out beats the heat, and gets us to Vegas for an early lunch….. But first the Hoover Dam! Vegas – Pools, shows, fun. We will have a lot of the day to explore Vegas, and the whole evening.

Day 16 – Las Vegas, NV to Big Bear Lake / Victorville, CA 224 miles

We take a little Rt 66 excursion up into the amazing San Bernadino 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 17 – Big Bear Lake / Victorville 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 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 bikes 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.

×

19 DAY – Route 66 Guided Motorcycle Tour

Guided Tours

DATES | PRICING | BOOKING

Self Drive Tours

DATES | PRICING | BOOKING

View Map

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 2 – Chicago to Springfield, Illinois- 185 miles

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

Today we ride over the famous old red brick section of Rt 66. It is a tucked away little gem. Amazing day riding Rt 66. Exploring St. Louis. Then we ride our bikes to the famous Rt 66 Chain of Rocks Bridge that goes over the mighty Mississippi River. The Gateway Arch welcomes travelers heading East or West. The famous Budweiser Brewery. Maybe a blues bar tonight?

Day 4 – St Louis to Lebanon, MO – 153 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 – Lebanon to Tulsa, OK – 233 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 – Tulsa to Clinton OK – 191 miles

Elk Cit Rt 66 Museum. Welcome to Texas! The panhandle of Texas. Big Texan Steakhouse for dinner?

Day 7 – Clinton to Amarillo, TX – 176 miles

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.

DAY 8 – Amarillo to Santa Fe, NM – 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, shopping, great walking around…. This is really an amazing Southwest town to spend time in. We discover the rich history and culture of Santa Fe after a big day riding Route 66 on our Harley Davidson.

Day 9 – Santa Fe, NM – Layover

Relax and enjoy this great town. We can take a short nice ride up into the beautiful mountains today. Or just enjoy a full day of rest and fun.

Day 10 – Santa Fe to Gallup – 199 miles

We start the day riding the curvy hills to Maggie’s Diner where the big showdown was in “Wild Hogs”. Then lunch in Old Town Albuquerque. Next 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 motorcycle. This is a relaxing day with an early arrival and an iconic destination.

Day 12 – Winslow to Grand Canyon National Park

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 13 – 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.

Day 14 – Williams to Laughlin, NV – 190 miles

The quintessential Western 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 15 – Laughlin, NV to Las Vegas, NV – 97 miles

An early morning ride out beats the heat, and gets us to Vegas for an early lunch….. But first the Hoover Dam! Vegas – Pools, shows, fun. We will have a lot of the day to explore Vegas, and the whole evening.

Day 16 – Las Vegas – Layover Day

Lots to do today. We have some great optional half day rides planned. Have fun with the group or explore Vegas on your own. Tons of fun activities to do.

Day 17 – Las Vegas, NV to Big Bear Lake (or Victorville), 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 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 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 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 bikes 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.

×

19 DAY – Route 66 Guided Motorcycle Tour Via Milwaukee

Guided Tours

DATES | PRICING | BOOKING

Self Drive Tours

DATES | PRICING | BOOKING

View Map

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 2 – Chicago to Milwaukee (Option 1) or Chicago to Milwaukee to Chicago (Option 2)

Let’s go! We ride on our motorcycles to the famous Harley-Davidson Museum in Milwaukee where we tour before heading out on Route 66 the next day.

Day 3 – Milwaukee (Or Chicago) to Springfield, Illinois- 185 miles

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 4 – Springfield, Illinois to Saint Louis- 175 miles

Today we ride over the famous old red brick section of Rt 66. It is a tucked away little gem. Amazing day riding Rt 66. Exploring St. Louis. Then we ride our bikes to the famous Rt 66 Chain of Rocks Bridge that goes over the mighty Mississippi River. The Gateway Arch welcomes travelers heading East or West. The famous Budweiser Brewery. Maybe a blues bar tonight?

Day 5 – St Louis to Lebanon, MO – 153 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 6 – Lebanon to Tulsa, OK – 233 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 7 – Tulsa to Clinton OK – 191 miles

Elk Cit Rt 66 Museum. Welcome to Texas! The panhandle of Texas. Big Texan Steakhouse for dinner?

Day 8 – Clinton to Amarillo, TX – 176 miles

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.

DAY 9 – Amarillo to Santa Fe, NM – 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, shopping, great walking around…. This is really an amazing Southwest town to spend time in. We discover the rich history and culture of Santa Fe after a big day riding Route 66 on our Harley Davidson.

Day 10 – Santa Fe, NM – Layover

Relax and enjoy this great town. We can take a short nice ride up into the beautiful mountains today. Or just enjoy a full day of rest and fun.

Day 11 – Santa Fe to Gallup – 199 miles

We start the day riding the curvy hills to Maggie’s Diner where the big showdown was in “Wild Hogs”. Then lunch in Old Town Albuquerque. Next 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 12 – Gallup to Grand Canyon National Park – 283 miles

We stand on a corner in Winslow, Arizona. 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 13 – 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.

Day 14 – Williams to Laughlin, NV – 190 miles

The quintessential Western 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 15 – Laughlin, NV to Las Vegas, NV – 97 miles

An early morning ride out beats the heat, and gets us to Vegas for an early lunch….. But first the Hoover Dam! Vegas – Pools, shows, fun. We will have a lot of the day to explore Vegas, and the whole evening.

Day 16 – Las Vegas – Layover Day

Lots to do today. We have some great optional half day rides planned. Have fun with the group or explore Vegas on your own. Tons of fun activities to do.

Day 17 – Las Vegas, NV to Big Bear Lake (or Victorville), 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 18 – Big Bear Lake / Victorville 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 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 bikes 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.

×

10 DAY – Route 66 Guided Motorcycle Tour

Guided Tours

DATES | PRICING | BOOKING

Self Drive Tours

DATES | PRICING | BOOKING

View Map

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 2 – Chicago to Springfield, Illinois –185 miles

Start 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

Today we ride over the famous old red brick section of Rt 66. It is a tucked away little gem. Amazing day riding Rt 66. Exploring St. Louis. Then we ride our bikes to the famous Rt 66 Chain of Rocks Bridge that goes over the mighty Mississippi River. The Gateway Arch welcomes travelers heading East or West. The famous Budweiser Brewery. Maybe a blues bar tonight?

Day 4 – St Louis to Lebanon, MO – 153 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 – Lebanon to Tulsa, OK – 233 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 – Tulsa to Clinton OK – 191 miles

Elk Cit Rt 66 Museum. Welcome to Texas! The panhandle of Texas. Big Texan Steakhouse for dinner?

Day 7 – Clinton to Amarillo, TX – 176 miles

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.

DAY 8 – Amarillo to Santa Fe, NM – 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 day riding Route 66 on our Harley Davidson.

Day 9 – Santa Fe to Albuquerque

We start the day slow today. First have a leisurely breakfast in Santa Fe. Stroll around the town square, or take a ride up into the mountains. Next we ride the curvy hills to Maggie’s Diner in Madrid where the big showdown was in “Wild Hogs”. Plenty of time to soak in the unique town of Madrid and have lunch. There are also some other neat stops we have added in on the way to Old Town Albuquerque where you spend the afternoon exploring.

Day 10 – Albuquerque Departure Day

×

9 DAY – Route 66 Guided Motorcycle Tour

Guided Tours

DATES | PRICING | BOOKING

Self Drive Tours

DATES | PRICING | BOOKING

View Map

Day 1 – Arrive in Albuquerque

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 in Old Town Albuquerque.

DAY 2 – Albuquerque to Gallup – ( On 5B Option, we ride to Santa Fe this day )

We start the day with breakfast in Old Town Albuquerque. Next 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. On 5B Option – we would add a day here, and this day Ride to Santa Fe, and the next day Ride through Madrid to see Maggie’s Diner and more, before getting to Gallup.

Day 3 – 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 4 – Grand Canyon South Rim 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.

Day 5 – Williams to Laughlin, NV – 190 miles

The quintessential Western 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 6 – Laughlin, NV to Las Vegas, NV – 97 miles

An early morning ride out beats the heat, and gets us to Vegas for an early lunch….. But first the Hoover Dam! Vegas – Pools, shows, fun. We will have a lot of the day to explore Vegas, and the whole evening.

Day 7 – Las Vegas, NV to Big Bear Lake (or Victorville), CA – 224 miles

We take a little Rt 66 excursion up into the amazing San Bernadino 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 8 – 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 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 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 bikes in at the end of the day. A victory dinner tonight!

Day 9 – 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.

Route 66 Motorcycle Tour Dates

Book

Contact Us FOR MORE DATES CONSTANTLY FORMING

Milwaukee Option: We start in Milwaukee and start 1 day earlier / add 1 day onto the trip in days in the pricing chart.

2021

Chicago to LA Motorcycle Tour – 15 Day 2021: April 13 – May 4, 11, 18 – June 1, 8, 29 – July 6, 20 – Aug 3, 17, 31 – Sept 7, 14, 21, 28 – Oct 12

Chicago to LA Motorcycle Tour – 16 Day – Ultra 2021: May 19-June 3, Aug 1-15, Aug 8-23, Sept 3-18, Sept 14-29

Chicago to LA Motorcycle Tour – 17 Day – Ultimate 2021: May 19-June 4, Aug 8-24, Sept 3-19, Sept 14-30, Oct 2-18

Chicago to LA Custom Featured Tour: 19 Day 2021: Aug 15 – Sept 2

Similar to the 17 Day but add 2 days: Harley Museum / Milwaukee + extra Vegas Night. Still has layover in Santa Fe also.

Tour Schedule with More Dates CONTACT US TO BOOK OR FOR QUESTIONS

2022 – Contact for 2023

Chicago to LA Motorcycle Tour – 15 Day 2022: April 13 – May 4, 11, 18 – June 1, 8, 29 – July 6, 20 – Aug 3, 17, 31 – Sept 7, 14, 21, 28 – Oct 12

Chicago to LA Motorcycle Tour – 16 Day – Ultra 2022: May 19-June 3, Aug 1-15, Sept 3-18, Sept 14-29

Chicago to LA Motorcycle Tour – 17 Day – Ultimate 2022: May 19-June 4, Sept 3-19, Sept 14-30, Oct 2-18

Chicago to LA Custom Featured Tour: 19 Day 2022: Aug 15 – Sept 2

Similar to the 17 Day but add 2 days: Harley Museum / Milwaukee + extra Vegas Night. Still has layover in Santa Fe also.

GUIDED MOTORCYCLE TOURS

Route 66 Motorcycle Guided Tour Pricing

Guided Tour – Per Person - TAX INCLUDED 8 Day 7 Night 9 Day 8 Night 10 Day 9 Night 13 Day 12 Night 15 D 14 Night 16D 15N Ultra 17D 16N Ultimate 18D 17N (17D plus Museum) 19D 18N EPIC

2 People – 1 Bike – 1 Room $2840 + $213 $2840 + $213 $3340 + $213 $4119 + $298 $4675 $5100 $5525 $6420 $6815

2 People – 2 Bikes – 1 Room $3590 + $425 $3590 + $425 $4200 + $425 $5776 + $595 $6115 $6990 $7595 $7995 $8595

1 Person – 1 Bike – 1 Room $4390 + $425 $4390 + $425 $4988 + $425 $6789 + $595 $7987 $8300 $8995 $9580 $9984

SELF DRIVE MOTORCYCLE TOURS

Route 66 Motorcycle Self Drive Tour Pricing

Self Drive Tour Per Person - TAX INCLUDED 9 Day 8 Night 1/2 trip 10 Day 9 Night 1/2 trip 13 Day 12 Night 14 Day 13 Night 15 Day 14 Night 16 Day 15 Night Ultra 17D 16N Ultimate 18D 17 Night 19D 18N EPIC

Self Drive – 2 People (1 rider 1 passenger ) 1 Bike 1 Room – each $1549 + $213 one way fee $1756+ $213 $2377 + $298 $2584 + $298 $2791 + $298 $2886 + $298 one way fee $3085 + $298 $3284 + $298 $3483 + $298 one way fee

Self Drive – 2 Riders 1 Room $2473 + $425 one way fee $2812 + $425 $3829 + $595 $4168 + $595 $4507 + $595 $4622 + $595 one way fee $4945 + $595 one way fee $5268 + $595 $5591 + $595 one way fee

Self Drive – 1 Rider 1 Room $3098 + $425 one way fee $3512 + $425 $4754 + $595 $5168 + $595 $5582 + $595 $5772 + $595 one way fee $6170 + $595 one way $6568 + $595 $6966 + $595 one way fee

Book

Guided Tour – Per Person - TAX INCLUDED	8 Day 7 Night	9 Day 8 Night	10 Day 9 Night	13 Day 12 Night	15 D 14 Night	16D 15N Ultra	17D 16N Ultimate	18D 17N (17D plus Museum)	19D 18N EPIC
2 People – 1 Bike – 1 Room	$2840 + $213	$2840 + $213	$3340 + $213	$4119 + $298	$4675	$5100	$5525	$6420	$6815
2 People – 2 Bikes – 1 Room	$3590 + $425	$3590 + $425	$4200 + $425	$5776 + $595	$6115	$6990	$7595	$7995	$8595
1 Person – 1 Bike – 1 Room	$4390 + $425	$4390 + $425	$4988 + $425	$6789 + $595	$7987	$8300	$8995	$9580	$9984

Self Drive Tour Per Person - TAX INCLUDED	9 Day 8 Night 1/2 trip	10 Day 9 Night 1/2 trip	13 Day 12 Night	14 Day 13 Night	15 Day 14 Night	16 Day 15 Night Ultra	17D 16N Ultimate	18D 17 Night	19D 18N EPIC
Self Drive – 2 People (1 rider 1 passenger ) 1 Bike 1 Room – each	$1549 + $213 one way fee	$1756+ $213	$2377 + $298	$2584 + $298	$2791 + $298	$2886 + $298 one way fee	$3085 + $298	$3284 + $298	$3483 + $298 one way fee
Self Drive – 2 Riders 1 Room	$2473 + $425 one way fee	$2812 + $425	$3829 + $595	$4168 + $595	$4507 + $595	$4622 + $595 one way fee	$4945 + $595 one way fee	$5268 + $595	$5591 + $595 one way fee
Self Drive – 1 Rider 1 Room	$3098 + $425 one way fee	$3512 + $425	$4754 + $595	$5168 + $595	$5582 + $595	$5772 + $595 one way fee	$6170 + $595 one way	$6568 + $595	$6966 + $595 one way fee