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
Sturgis Self Drive Car Tour - Chicago to Las Vegas
Sturgis Bike Week Self Drive Car Tour: Chicago, Harley-Davidson Museum and Factory Tour, Sturgis, Colorado Rockies, Monument Valley, Grand Canyon, Route 66, Las Vegas Sturgis Bike Week Self Drive Car Tour Some Pictures from 2017 Sturgis Motorcycle Tour
Route 66 Self Drive 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 Self Drive 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.
Day 1 – Arrive in Chicago 30 minutes – 20 miles – car orientation
We meet after lunchtime at our hotel and talk about our upcoming adventure on the Mother Road of America, Route 66 Chicago to LA. We will pick up the cars at 4pm and do an orientation to familiarize ourselves. We then take the van to the beginning of Route 66 in downtown Chicago for dinner and to discuss our big adventure!
Day 2 – Chicago to Milwaukee, WI 2hr 24min – 92 miles
We’ll get an early start today and head north along Lake Michigan to see history roar to life at the Harley Davidson Museum, one of Milwaukee’s top destinations. The museum features more than 450 motorcycles and artifacts, dating back to Serial Number One, the oldest known Harley-Davidson® motorcycle.
Day 3 – Milwaukee to La Crosse, WI 4hr 10min – 256 miles
This morning we’ll head out from Milwaukee to Menomonee Falls for the Harley Davidson Powertrain Operations facility, home of the “Big Twin.” On the factory tour, we’ll see the assembly line and machining areas where employees produce engines and transmissions for Touring, Softail,® Dyna® and Sportster® model families. Then a nice drive through the American countryside. We’ll finish up the driving day in La Crosse, Wisconsin on the banks of the Mississippi River.
Day 4 – La Crosse to Mitchell, SD 5hr 34min – 363 miles
On this day we will cross Minnesota, known as The Land of 10,000 Lakes. This is a long driving day, and we’re covering a lot of miles to get us into Sturgis country.
Day 5 – Mitchell to Deadwood, SD / arrive Sturgis – night 1 4hr 52min – 314 miles + Badlands
You’ll feel like you’re on the moon as we travel through South Dakota by way of the Badlands. This National Park contains over 300 square miles of sharply erodes buttes, pinnacles and spires blended with the largest undisturbed mixed grass prairie in the United States. Tonight we’ll be in Deadwood, ready for the Sturgis Rally.
Day 6 – Sturgis Rally / Deadwood, SD – night 2 Mileage Optional
Day 7 – Sturgis Rally / Deadwood, SD – night 3 Mileage Optional
We’ll take two full days to experience the roar and rumble of one of the largest motorcycle gatherings in the world, the 76th Annual Sturgis Motorcycle Rally. There are concerts, races, and bike shows; as well as blocks of Main Street bikes-only street vibe. Optional excursions include riding through the Black Hills National Forest to see Mount Rushmore and the buffalo in Custer State Park.
DAY 8 – Deadwood / Sturgis to Cheyenne, WY 4hr 44min – 274 miles
We’ll head out of Sturgis for the last time and say goodbye to the Great Plains, and point our cars towards the town of Cheyenne, home of the American Cowboy. We give our cars a well-deserved rest as we check out the local saloons and take a rest ourselves.
Day 9 – Cheyenne to Buena Vista, CO 5hr 17min – 280 miles
Leaving Cheyenne, we’ll travel through the Colorado Mountains most of the day. We climb high into the Rockies in our cars to the Trail Ridge Pass, elevation 12,095 feet. Then on through the Arkansas River Valley to the town of Buena Vista.
Day 10 – Buena Vista to Durango, CO 4hr 55min – 253 miles
We’ll travel through the scenic mountains and National Forests of Colorado to arrive in the Old West town of Durango. This historic town has been the setting for scenes in many Wild West movies such as Butch Cassidy and the Sundance Kid.
Day 11 – Durango to Kayenta, AZ 3hr 38min – 201 miles + Park
On this day we will explore the towering sandstone buttes of of Monument Valley Navajo Tribal Park. But first we will visit the 4 Corners National Monument where four states meet. The 17-mile Valley Drive gives spectacular views of the red-sand desert and distinctive butte formations, and is also a recognizable location from Western movies. We will get you a picture of you in your car at the most iconic Old West Monument Valley spot in the USA.
Day 12 – Kayenta to Grand Canyon National Park, AZ 2hr 45min – 155 miles
An amazing ride up to the Grand Canyon. That is one big hole! Spectacular scenery and canyons on the way. We stop at a real Indian trading post to buy some souvenirs before we get to the South Rim of the Grand Canyon for one of the best sunsets in the world.
Day 13 – Grand Canyon to Kingman, AZ 3hr 19min – 189 miles
Leaving the Grand Canyon, we’ll head south through Arizona with a stop in Seligman before we take a stretch of old Route 66 through almost forgotten towns like Valentine and Hackberry. We will have plenty of time to explore one of the most famous stretches of Route 66 in our cars. We’ll overnight in Kingman, on the eastern edge of the Mojave Desert.
Day 14 – Kingman to Las Vegas 3hr 5min – 154 miles + 1hr Hoover Dam (drop cars off 4 pm – end of guided tour)
First we will head to the old mining town of Oatman, then head for Vegas. We might make a stop at the famous Hoover Dam if the desert has not cooked us. Vegas Baby! We made it! We’ll pull into Vegas and cruise the scenic strip. After turning in the cars at 4pm, you’re free to hit the town.
Day 1 – Arrive in Chicago 30 minutes – 20 miles – car orientation
We meet after lunchtime at our hotel and talk about our upcoming adventure on the Mother Road of America, Route 66 Chicago to LA. We will pick up the cars at 4pm and do an orientation to familiarize ourselves. We then take the van to the beginning of Route 66 in downtown Chicago for dinner and to discuss our big adventure!
Day 2 – Chicago to Milwaukee, WI 2hr 24min – 92 miles
We’ll get an early start today and head north along Lake Michigan to see history roar to life at the Harley Davidson Museum, one of Milwaukee’s top destinations. The museum features more than 450 motorcycles and artifacts, dating back to Serial Number One, the oldest known Harley-Davidson® motorcycle.
Day 3 – Milwaukee to La Crosse, WI 4hr 10min – 256 miles
This morning we’ll head out from Milwaukee to Menomonee Falls for the Harley Davidson Powertrain Operations facility, home of the “Big Twin.” On the factory tour, we’ll see the assembly line and machining areas where employees produce engines and transmissions for Touring, Softail,® Dyna® and Sportster® model families. Then a nice drive through the American countryside. We’ll finish up the driving day in La Crosse, Wisconsin on the banks of the Mississippi River.
Day 4 – La Crosse to Mitchell, SD 5hr 34min – 363 miles
On this day we will cross Minnesota, known as The Land of 10,000 Lakes. This is a long driving day, and we’re covering a lot of miles to get us into Sturgis country.
Day 5 – Mitchell to Deadwood, SD / arrive Sturgis – night 1 4hr 52min – 314 miles + Badlands
You’ll feel like you’re on the moon as we travel through South Dakota by way of the Badlands. This National Park contains over 300 square miles of sharply erodes buttes, pinnacles and spires blended with the largest undisturbed mixed grass prairie in the United States. Tonight we’ll be in Deadwood, ready for the Sturgis Rally.
Day 6 – Sturgis Rally / Deadwood, SD – night 2 Mileage Optional
We’ll take two full days to experience the roar and rumble of one of the largest motorcycle gatherings in the world, the 76th Annual Sturgis Motorcycle Rally. There are concerts, races, and bike shows; as well as blocks of Main Street bikes-only street vibe. Optional excursions include riding through the Black Hills National Forest to see Mount Rushmore and the buffalo in Custer State Park.
Day 7 – Sturgis Rally / Deadwood, SD – night 3 Mileage Optional
DAY 8 – Deadwood / Sturgis to Cheyenne, WY 4hr 44min – 274 miles
We’ll head out of Sturgis for the last time and say goodbye to the Great Plains, and point our cars towards the town of Cheyenne, home of the American Cowboy. We give our cars a well-deserved rest as we check out the local saloons and take a rest ourselves.
Day 9 – Cheyenne to Buena Vista, CO 5hr 17min – 280 miles
Leaving Cheyenne, we’ll travel through the Colorado Mountains most of the day. We climb high into the Rockies in our cars to the Trail Ridge Pass, elevation 12,095 feet. Then on through the Arkansas River Valley to the town of Buena Vista.
Day 10 – Buena Vista to Durango, CO 4hr 55min – 253 miles
We’ll travel through the scenic mountains and National Forests of Colorado to arrive in the Old West town of Durango. This historic town has been the setting for scenes in many Wild West movies such as Butch Cassidy and the Sundance Kid.
Day 11 – Durango to Kayenta, AZ 3hr 38min – 201 miles + Park
On this day we will explore the towering sandstone buttes of of Monument Valley Navajo Tribal Park. But first we will visit the 4 Corners National Monument where four states meet. The 17-mile Valley Drive gives spectacular views of the red-sand desert and distinctive butte formations, and is also a recognizable location from Western movies. We will get you a picture of you in your car at the most iconic Old West Monument Valley spot in the USA.
Day 12 – Kayenta to Grand Canyon National Park, AZ 2hr 45min – 155 miles
An amazing ride up to the Grand Canyon. That is one big hole! Spectacular scenery and canyons on the way. We stop at a real Indian trading post to buy some souvenirs before we get to the South Rim of the Grand Canyon for one of the best sunsets in the world.
Day 13 – Grand Canyon to Kingman, AZ 3hr 19min – 189 miles
Leaving the Grand Canyon, we’ll head south through Arizona with a stop in Seligman before we take a stretch of old Route 66 through almost forgotten towns like Valentine and Hackberry. We will have plenty of time to explore one of the most famous stretches of Route 66 in our cars. We’ll overnight in Kingman, on the eastern edge of the Mojave Desert.
Day 14 – Kingman to Laughlin
First we will head to the old mining town of Oatman, then head for Vegas. We might make a stop at the famous Hoover Dam if the desert has not cooked us. Vegas Baby! We made it! We’ll pull into Vegas and cruise the scenic strip. After turning in the cars at 4pm, you’re free to hit the town.
We meet after lunchtime at our hotel and talk about our upcoming adventure on the Mother Road of America, Route 66 Chicago to LA. We will pick up the cars at 4pm and do an orientation to familiarize ourselves with our cars. We then take the van to the beginning of Route 66 in downtown Chicago for dinner and to discuss our big adventure!
Day 2 - Chicago to Milwaukee, WI 2hr 24min – 92 miles
We’ll get an early start today and head north along Lake Michigan to see history roar to life at the Harley Davidson Museum, one of Milwaukee’s top destinations. The museum features more than 450 motorcycles and artifacts, dating back to Serial Number One, the oldest known Harley-Davidson® motorcycle.
Day 3 - Milwaukee to La Crosse, WI 4hr 10min – 256 miles
This morning we’ll head out from Milwaukee to Menomonee Falls for the Harley Davidson Powertrain Operations facility, home of the “Big Twin.” On the factory tour, we’ll see the assembly line and machining areas where employees produce engines and transmissions for Touring, Softail,® Dyna® and Sportster® model families. Then a nice ride through the American countryside. We’ll finish up the riding day in La Crosse, Wisconsin on the banks of the Mississippi River.
Day 4 - La Crosse to Mitchell, SD 5hr 34min – 363 miles
On this day we will cross Minnesota, known as The Land of 10,000 Lakes. This is a long driving day, and we’re covering a lot of miles to get us into Sturgis country.
Day 5 Mitchell to Deadwood, SD / arrive Sturgis – night 1 4hr 52min – 314 miles + Badlands
You’ll feel like you’re on the moon as we travel through South Dakota by way of the Badlands. This National Park contains over 300 square miles of sharply erodes buttes, pinnacles and spires blended with the largest undisturbed mixed grass prairie in the United States. Tonight we’ll be in Deadwood, ready for the Sturgis Rally.
Days 6 – Sturgis Rally / Deadwood, SD – night 2 Mileage Optional
We’ll take four nights to experience the roar and rumble of one of the largest motorcycle gatherings in the world, the Annual Sturgis Motorcycle Rally. There are concerts, races, and bike shows; as well as blocks of Main Street bikes-only street vibe. Optional excursions include riding through the Black Hills National Forest to see Mount Rushmore and the buffalo in Custer State Park.
Days 7 – Sturgis Rally / Deadwood, SD – night 3 Mileage Optional
Days 8 – Sturgis Rally / Deadwood, SD – night 4
Day 9 - Deadwood / Sturgis to Buffalo, WY – 2hr 36min – 183 miles , or 4hr remote ride
We’ll head out of Sturgis for the last time and say goodbye to the Sturgis Motorcycle Rally, and point our cars towards the Rocky Mountains. We drive our cars over some nice smaller mountains today, and stay in neat western town tonight. One day closer to an amazing mountain ride on the Bear Tooth Highway, and one day closer to Bonneville Speed Week in our cars.
Depending on what time we leave Sturgis in the morning, the weather, and what we will see on the way out of town…. we will either take the more direct or longer remote route today. Many of our days we have multiple routes we choose from depending on current factors and variables.
Day 10 – Buffalo, Wyoming to Cody – 3:10 hr – 181 miles
Pass through the Bighorn National Forest today. Just a nice cruising day with some neat stops. The vast landscape opens again on our tour.
Day 11 – Cody to Cooke via Bear Tooth Highway – 2:45 hr – 127 miles
Start the day in Cody then the Beginning of the amazing Bear Tooth Highway from the town of Red Lodge. As our Sturgis Motorcycle tour progresses, you will have completely forgotten about Sturgis by this time. Take time and watch the complete video above as we climb the Bear Tooth Highway. This is my favorite day of the trip. If only every day driving cars on tour could be like this day. For lunch the cool town of Red Lodge has some great food.
Day 12 – Cooke to Jackson
Day 13 – Jackson to Salt Lake City
Day 14 – Salt Lake to Wendover / Bonneville Speed Week
We arrive around lunch or earlier to have the afternoon and night at Bonneville Speed Week. We will walk around the pits and watch the races. Tonight we party with all the racers!
Day 15 – Bonneville Speed Week to Ely
First we get up at the crack of dawn and get onto the salt early to be there when the sun comes up. The weather is nice and cool in the morning. Absolutely amazing experience to watch the sun come up over the Salt as you listen to the race cars fire up and race, and smell the sweet smell of racing gas in the air. The fastest cars run early in the morning when the weather is cool and the air is dense. They get the fastest times this way. And it is the best time to be out there. Then a beautiful ride today though the remote desert mountains and hills.
Day 16 – Ely to Las Vegas
Another nice drive through the desert heading into Vegas where we get a picture in front of the Las Vegas sign on the strip, and one in front of Las Vegas Harley Davidson. Tonight we have our last dinner together and reminisce about our amazing journey together before we say our goodbyes and set you loose on the Vegas Strip!
Sturgis Car Tours 2021: – MORE DATES POSSIBLE FORMING – CONTACT US
(Sturgis Rally Aug 6-15, 2021 / Bonneville Speedweek is Aug 7-13, 2021)
July 27- Aug 10, 2021 – Denver to Denver – 15 Day Car Tour ( 14 Day +1 with extra time in Yellowstone )
July 30- Aug15, 2021 – Chicago, Harley Museum, Sturgis, Bonneville, Vegas – 17 Day Car Tour
Aug 1-15, 2021 – Chicago to Museum, Monument Valley, Grand Canyon, Vegas- option – 16 day Car Tour
Sturgis Car Self Drive Tour Pricing – Chicago to Las Vegas, with Bonneville Speed Week option
Self Drive Car Tour - per person - TAX INCLUDED
15 Day 14 Night – w/ Grand Canyon
16 Day 15 Night – w/ Grand Canyon
17 Day 16 Night – w/ Bonneville
Self Drive – 2 people 1 car - 1 room
$
$
$
Self Drive – 2 Drivers - 2 cars - 1 room
$
$
$
Self Drive - 1 Driver - 1 car- 1 room
$
$
$
add $605 one way fee PER CAR
There is a $595 Return Fee per car if dropped in Las Vegas
Sturgis Hotel Surcharge depending on how many nights in Sturgis and which hotel options ( Deadwood, Rapid City, Sturgis downtown)
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 
