The Ride Free Tour was the

BEST TRIP OF MY LIFE

- Eric “Champion du monde”

Thefaine, France

Route 66

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Thank you for

THE BEST VACATION EVER.

– Bill and Judy Gore, Australia

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Riding with Ride Free brought back all kinds of memories.

I LOVED THE TOUR.

- Elmer ”Ironman”, Alaska, USA

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The tour I did with Ride Free was one of the

BEST MOMENTS OF MY LIFE.

- Fabien ”Speedo” Graille, France

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The Ride Free Tour was the

BEST TRIP OF MY LIFE.

- Eric “Champion du monde”

Thefaine, France

Route 66

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Riding on your tour was a

SENSATIONAL EXPERIENCE.

- Julie Tran, Los Angeles, USA

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Sturgis Guided Car Tour Chicago to Las Vegas

TOUR INFORMATION | WHAT’S INCLUDED | CAR CHOICES | WHERE WE STAY | GUIDED TOUR FAQ’S

Why Choose Our Guided Car Tour?

Guided Tour

Anyone can do it
Follow the tour guide
Bring and meet new friends
Just show up and have fun
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Amazing Experience

Fulfill your dream
Great adventure
Local hotels and restaurants
Take you to the great stops
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Late Model Muscle Cars

Mustangs, Camaros, Challengers
Easy and fun to drive
Put the top down in convertibles
Other car options available
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15 DAY ITINERARY

Chicago – Sturgis – Rt 66 – Grand Canyon – Monument Valley – Vegas

16 DAY ITINERARY

Chicago – Sturgis – Rt 66 – Grand Canyon – Monument Valley – Vegas

17 DAY ITINERARY

Chicago – Sturgis – Bonneville – Yellowstone – Vegas

DEALS AND SPECIALS

EARLY BOOKING DISCOUNT

PASSENGERS RIDE FREE

DEALS AND SPECIALS

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

What a fantastic trip. My friend and I spent 2 years discussing this trip and eventually settled on the fantastic team at Ride Free. What quickly convinced us... read more

Jantjevdp
10/26/2019

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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

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TOUR INFORMATION

Sturgis Guided Car Tour - Chicago to Las Vegas

Sturgis Bike Week Guided Car Tour: Chicago, Harley-Davidson Museum and Factory Tour, Sturgis, Colorado Rockies, Monument Valley, Grand Canyon, Route 66, Las Vegas
Sturgis Bike Week Guided Motorcycle Tour
Some Pictures from 2017 Sturgis Motorcycle Tour

We also have an 11 and 14 Day Denver to Denver Sturgis Motorcycle Tour ( click here for that option )

Tour Options – CONTACT US For 2019 Dates
-15 Day – July 29- Aug 12, 2018 – Chicago to Las Vegas via Sturgis 3 nights
-16 Day – July 29 -Aug 13,2017 – Chicago to Las Vegas via Sturgis 4 nights/ Colorado / Monument Valley / Grand Canyon / Rt 66
– 17 Day – July 29 – Aug 14, 2017 -Chicago to Las Vegas / 4 nights Sturgis / Bear Tooth Highway / Yellowstone / Jackson / BONNEVILLE SPEED WEEK
-Optional Extension – 8 Day – Vegas / Rt 66 to LA to California Coast to San Francisco

PICTURES from 2012 Sturgis Tour First half of tour – 12 day tour
PICTURES from 2012 Sturgis Tour   Second half of tour – 12 day tour
VIDEOS from 2012 Sturgis Tour
2013 Sturgis Motorcycle Tour Pics     Vegas to Vegas 19 Day

15 Day ITINERARY with Grand Canyon and Monument Valley / Southern Route – below
17 Day ITINERARY with Bonneville and Bear Tooth Highway – below 15 day
TOUR PRICING below that
GUIDED TOUR FAQ’S FREQUENTLY ASKED QUESTIONS
SELF-DRIVE TOUR FAQ’S FREQUENTLY ASKED QUESTIONS

ROUTE ITINERARY BELOW FOR Chicago / Harley Museum / Sturgis 4 nights / Bear Tooth Highway / Yellowstone / Jackson / Bonneville Speed Week / Vegas
17 Day Itinerary – July 29 – August 14, 2018 – 4 nights Sturgis
Click for Some Pictures from 2017 Sturgis Motorcycle Tour
Bonneville Speed Week Aug 11-17, 2018 http://www.scta-bni.org

very rough map of route of travel

Day 1 – July 29, 2018 – Sun –   Meet Chicago – Meet 3pm at hotel provided. Pick up bikes at end of day at 4pm, then welcome dinner. So ready to leave in early am
Day 2 – July 30 – Mon –    Chicago to Harley Museum / Milwaukee
Day 3 – July 31 – Tues –    Harley Museum / Milwaukee to La Crosse
Day 4 – Aug 1 – Wed –     La Crosse to Mitchell
Day 5 – Aug 2- Thurs –   Mitchell to Sturgis – 1st night Sturgis
Day 6 – Aug 3 – Fri – Sturgis to Sturgis   – 2nd night Sturgis
Day 7 – Aug 4 – Sat – Sturgis to Sturgis – 3rd night Sturgis
Day 8 – Aug 5- Sun – Sturgis to Sturgis – 4th night Sturgis
Day 9 – Aug 6 – Mon – Sturgis to Buffalo
Day 10 – Aug 7 – Tues – Buffalo   to Cody
Day 11 – Aug 8 – Wed – Cody to Cooke – Bear Tooth HIghway Day
Day 12 – Aug 9 – Thurs- Cooke to Jackson – Yellowstone Day
Day 13 – Aug 10 – Fri – Jackson to Salt Lake – 4hr 33 min
Day 14 – Aug 11 – Sat – Salt Lake to Wendover / Bonneville on the way. 1.75hrs to Bonneville
( Aug 11-17, 2018 = Bonneville Speed Week Dates )
Day 15- Aug 12 – Sun – Wendover to Ely   – 1hr 53 = get to see sunrise at bville in am and racing
Day 16 – Aug 13 – Mon – Ely to Vegas          3hr 43 min
Day 17- Aug 14 – Tues – Vegas Departure Day

What’s Included Sturgis All Inclusive Motorcycle Tour– Gas, Tour Guide, Support Vehicle with driver , National Park Fees, Motorcycle, Lodging.

-$45 + tax a day event surcharge by the rental company on the days of the rally. Depending on which tour you are on, that fee varies.
-Sturgis Hotel Surcharge depending on how many nights in Sturgis and which hotel options ( Deadwood, Rapid City, Sturgis downtown)
-$595 Return Fee per motorcycle if dropped in Las Vegas

15 DAY - Sturgis Chicago to Las Vegas

Guided Car Tour

Guided Tours

DATES | PRICING | BOOKING

Self Drive Tours

DATES | PRICING | BOOKING

View Map

Day 1 – Arrive in Chicago 30 minutes – 20 miles – bike 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 – 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 bikes 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 15 Departure Las Vegas

16 DAY - Sturgis Chicago to Las Vegas

Guided Car Tour

Guided Tours

DATES | PRICING | BOOKING

Self Drive Tours

DATES | PRICING | BOOKING

View Map

Day 1 – Arrive in Chicago 30 minutes – 20 miles – bike orientation

Day 2 – Day 2 Chicago to Milwaukee, WI 2hr 24min – 92 miles

Day 3 – Milwaukee to La Crosse, WI 4hr 10min – 256 miles

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

Day 6 – Sturgis Rally / Deadwood, SD – night 2 Mileage Optional

Day 7 – Sturgis Rally / Deadwood, SD – night 3 Mileage Optional

DAY 8 – Deadwood / Sturgis to Cheyenne, WY 4hr 44min – 274 miles

Day 9 – Cheyenne to Buena Vista, CO 5hr 17min – 280 miles

Day 10 – Buena Vista to Durango, CO 4hr 55min – 253 miles

Day 11 – Durango to Kayenta, AZ 3hr 38min – 201 miles + Park

Day 12 – Kayenta to Grand Canyon National Park, AZ 2hr 45min – 155 miles

Day 13 – Grand Canyon to Kingman, AZ 3hr 19min – 189 miles

Day 14 – Kingman to Laughlin

Day 15 – Laughlin to Las Vegas

Day 16 Departure Las Vegas

17 DAY - Sturgis Chicago to Las Vegas

Guided Car Tour

Guided Tours

DATES | PRICING | BOOKING

Self Drive Tours

DATES | PRICING | BOOKING

View Map

Day 1 Arrive in Chicago

Day 2 Chicago to Milwaukee, WI 2hr 24min – 92 miles

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

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 riding motorcycles 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!

Day 17 – Las Vegas Departure Day

Departure Day

Sturgis Guided Car Tour Chicago to Las Vegas

Why Choose Our Guided Car Tour?

Guided Tour

Amazing Experience

Late Model Muscle Cars

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TOUR INFORMATION

Sturgis Guided Car Tour - Chicago to Las Vegas

15 DAY - Sturgis Chicago to Las Vegas

Guided Car Tour

Day 1 – Arrive in Chicago 30 minutes – 20 miles – bike orientation

Day 2 – Day 2 Chicago to Milwaukee, WI 2hr 24min – 92 miles

Day 3 – Milwaukee to La Crosse, WI 4hr 10min – 256 miles

Day 4 – La Crosse to Mitchell, SD 5hr 34min – 363 miles

Day 5 – Mitchell to Deadwood, SD / arrive Sturgis – night 1 4hr 52min – 314 miles + Badlands

Day 6 – Sturgis Rally / Deadwood, SD – night 2 Mileage Optional

Day 7 – Sturgis Rally / Deadwood, SD – night 3 Mileage Optional

DAY 8 – Deadwood / Sturgis to Cheyenne, WY 4hr 44min – 274 miles

Day 9 – Cheyenne to Buena Vista, CO 5hr 17min – 280 miles

Day 10 – Buena Vista to Durango, CO 4hr 55min – 253 miles

Day 11 – Durango to Kayenta, AZ 3hr 38min – 201 miles + Park

Day 12 – Kayenta to Grand Canyon National Park, AZ 2hr 45min – 155 miles

Day 13 – Grand Canyon to Kingman, AZ 3hr 19min – 189 miles

Day 14 – Kingman to Las Vegas 3hr 5min – 154 miles + 1hr Hoover Dam (drop bikes off 4 pm – end of guided tour)

Day 15 Departure Las Vegas

16 DAY - Sturgis Chicago to Las Vegas

Guided Car Tour

Day 1 – Arrive in Chicago 30 minutes – 20 miles – bike orientation

Day 2 – Day 2 Chicago to Milwaukee, WI 2hr 24min – 92 miles

Day 3 – Milwaukee to La Crosse, WI 4hr 10min – 256 miles

Day 4 – La Crosse to Mitchell, SD 5hr 34min – 363 miles

Day 5 – Mitchell to Deadwood, SD / arrive Sturgis – night 1 4hr 52min – 314 miles + Badlands

Day 6 – Sturgis Rally / Deadwood, SD – night 2 Mileage Optional

Day 7 – Sturgis Rally / Deadwood, SD – night 3 Mileage Optional

DAY 8 – Deadwood / Sturgis to Cheyenne, WY 4hr 44min – 274 miles

Day 9 – Cheyenne to Buena Vista, CO 5hr 17min – 280 miles

Day 10 – Buena Vista to Durango, CO 4hr 55min – 253 miles

Day 11 – Durango to Kayenta, AZ 3hr 38min – 201 miles + Park

Day 12 – Kayenta to Grand Canyon National Park, AZ 2hr 45min – 155 miles

Day 13 – Grand Canyon to Kingman, AZ 3hr 19min – 189 miles

Day 14 – Kingman to Laughlin

Day 15 – Laughlin to Las Vegas

Day 16 Departure Las Vegas

17 DAY - Sturgis Chicago to Las Vegas

Guided Car Tour

Day 2 Chicago to Milwaukee, WI 2hr 24min – 92 miles

Day 3 Milwaukee to La Crosse, WI 4hr 10min – 256 miles

Day 4 La Crosse to Mitchell, SD 5hr 34min – 363 miles

Day 5 Mitchell to Deadwood, SD / arrive Sturgis – night 1 4hr 52min – 314 miles + Badlands

Days 6 – Sturgis Rally / Deadwood, SD – night 2 Mileage Optional

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

Day 10 – Buffalo, Wyoming to Cody – 3:10 hr – 181 miles

Day 11 – Cody to Cooke via Bear Tooth Highway – 2:45 hr – 127 miles

Day 12– Cooke to Jackson

Day 13– Jackson to Salt Lake City

Day 14 – Salt Lake to Wendover / Bonneville Speed Week

Day 15 – Bonneville Speed Week to Ely

Day 16 – Ely to Las Vegas

Day 17 – Las Vegas Departure Day