Take in stunning views are you ride through Arizona
Take in stunning views are you ride through Arizona
Missouri Hicks on Route 66
Missouri Hicks on Route 66
Ride the famous Route 66
Ride the famous Route 66
Route 66 with Eagle Riders
Route 66 with Eagle Riders
Hackberry Fuel Pumps along Route 66, Arizona
Hackberry Fuel Pumps along Route 66, Arizona
Route 66, Springfield
Route 66, Springfield

Route 66 Guided Motorcycle Tour

14 nights from €5,499 per person Including Flights


The world-renowned Route 66 motorcycle tour spans 2400 miles across 15 nights along the "Mainstreet of America." Pick up your bike from Chicago and ride to Los Angeles, on this iconic journey traverses eight states and three time zones. Route 66, the "Mother Road," boasts a rich history as the path of migrants, dreamers, and vacationers heading west. Preserving its 1950s charm, the route features classic infrastructure, making it an ideal road for motorcycle touring through diverse landscapes and vibrant Americana.

You will have an expert motorcycle guide throughout your time travelling with fellow riders. Your accommodation is pre-booked, and your luggage will be followed closely behind you to each destination so no need to worry how your suitcase will fit on the back. You can book your own motorcycle for an additional supplement.

Choose from a range of Harley models, including the Harley-Davidson Street Glide Touring Edition, Electra Glide, Street Glide, Road Glide, Heritage Softail Classic, Street Bob, Road Glide Ultra, and Road Glide Touring Edition. For a different riding experience, sport touring models like the Yamaha FJR1300 and Yamaha Super Tenere 1200 are also available. (ER)


  • Experience the vibrant Windy City of Chicago, known as the 'Paris of the Prairie.' See the stunning skyline along Lake Michigan, top-rated museums, diverse restaurants, and lively jazz and blues venues.
  • Journey through rolling Missouri hills, explore Devil’s Elbow's twisting roads, and discover Route 66 icons.
  • Visit Cadillac Ranch, explore the ghost town of Glen Rio, and enter the land of the Comanche Indians. Head to the High Plains and the altitude of Santa Fe, a beautiful and historic city.
  • Cross into Arizona, explore Petrified Forest National Park, and witness a fossilized prehistoric forest. Reach the Grand Canyon's South Rim for a dream-like evening with a sunset view.
  • End in the your exhilarating tour in Santa Monica, Los Angeles at the “End of the Trail” sign

Itinerary Overview

Fly into Chicago, IL 1 night – Springfield, IL 1 night – St. Louis, MO 1 night – Joplin, MO 1 night – Oklahoma City, OK 1 night – Amarillo, TX 1 Night, Santa Fe, NM 2 nights – Gallup, NM 1 night – Grand Canyon, AZ 1 night – Laughlin, NV 1 night – Las Vegas, NV 1 night – Victorville, CA 1 night, Los Angeles, CA 1 night – Fly home from Los Angeles

Alternatively, if you wanted a shorter tour, start from Chicago and end in Albuquerque, NM after 7-nights, then how about flying onto California for a relaxing break? Speak to our sales experts for further information.

2024 Definite Departure Dates

May: 02, 08, 09, 23, 30
Jun: 20, 27
Jul: 11, 25
Aug: 08, 22, 29
Sep: 04, 05, 12, 19
Oct: 05, 17

2025 Definite Departure Dates

Apr: 03, 24,
May: 07, 08, 22, 28, 29
June: 19, 26
Jul: 10, 24
Aug: 07, 21, 28
Sept: 03, 05, 11
Oct: 02, 16

Our holidays include
  • Flights & taxes
  • Accommodation
  • Checked baggage
  • CAR licensed & bonded
  • In resort assistance & 24 hour contact centre
Why Book with American Sky?
  • Hassle-free - book direct quickly and easily
  • Choice of airlines and the option to switch
  • A friendly, family run business with a wealth of experience.
  • Great deals on offer for multiple destinations
  • Low deposits
Why American Sky?
Your money is safe We safeguard your money with ATOL protection and have membership to codes of best conduct.
Why American Sky?
Award Winning
We answer quickly On average, calls are answered within three rings. We also respond within hours to emails.
Why American Sky?
Award Winning
We offer expert advice and great service Our luxury tailor-made holidays are created with impeccable service from start to finish.

Day 1

Chicago, IL

Welcome to the vibrant Windy City! Known as the 'Paris of the Prairie,' Chicago boasts a stunning skyline along Lake Michigan, top-rated museums, diverse restaurants, and lively jazz and blues venues. Make your way independently from the airport to your accommodation and see the city at leisure. This evening join your Orientation Meeting and Welcome Dinner as you embark on your dream Route 66 journey!

Overnight: Chicago. Welcome dinner included

Day 2

Chicago, IL – Springfield, IL (271 miles)

Embark on the ultimate American road trip as you pick up your bike in Chicago. Follow the legendary Route 66 from Illinois to the Pacific Coast, exploring the Pontiac Trail. Pass through Joliet, visit the incredible Route 66 Museum in Pontiac, and feel the essence of the Mother Road beneath your wheels.

Overnight: Springfield. Breakfast included

Day 3

Springfield, IL – St. Louis, MO (116 miles)

Today, we journey towards St. Louis, staying on the 2-lane sections of the Mother Road, passing through cornfields and small heartland towns. Arrival over the Chain of Rocks Bridge, the original Route 66 crossing of the Mississippi River. Enjoy the short ride into the music-filled "Gateway to the West," St. Louis, home to exceptional live music and BBQ ribs along the mighty Mississippi River.

Overnight: St. Louis. Breakfast included

Day 4

St. Louis, MO – Joplin, MO (335 miles)

Rise early for a view of the St. Louis Arch and Mississippi River before hitting the road. Journey through the rolling Missouri hills, visit the World’s Largest Rocking Chair in Fanning, explore Devil’s Elbow's twisting roads, and discover Route 66 icons. In Joplin, hear locals' tales about surviving the 2011 tornado over a stay and perhaps gather amazing stories from those who experienced the massive tornado firsthand.

Overnight: Joplin. Breakfast included

Day 5

Joplin, MO – Oklahoma City, OK (255 miles)

Today's focus is on the route! From Joplin, journey west through hills and horse country in Oklahoma, passing by Miami, Claremore, and Catoosa, home of the legendary Blue Whale. Traverse Tulsa, experiencing the reservations of Native American tribes, including Choctaw, Chickasaw, Seminole, Creek, and Cherokee. Tonight, rest in Oklahoma City, the heart and soul of Route 66. Explore Bricktown's vibrant restaurants, bars, and shops for a lively evening.

Overnight: Oklahoma. Breakfast included

Day 6

Oklahoma City, OK – Amarillo, TX (266 miles)

Embark on the historic stretches of Oklahoma’s Route 66, once home to vast buffalo herds and cattle trails. Ride the Chisholm Trail through Yukon and El Reno, visit the Route 66 Museum in Clinton, and cross into the Texas Panhandle. Consider an optional visit to the renowned Big Texan Steakhouse in Amarillo for a guaranteed taste of the best steaks in Texas!

Overnight: Amarillo. Breakfast included

Day 7

Amarillo, TX – Santa Fe, NM (303 miles)

Today, depart Texas for "The Land of Enchantment," New Mexico. Visit Cadillac Ranch, stop at Route 66's midway point in Adrian, explore the ghost town of Glen Rio, and enter the land of the Comanche Indians. Head to the High Plains and the altitude of Santa Fe, a beautiful and historic city, your base for the next two nights.

Overnight: Santa Fe. Breakfast included

Day 8

Santa Fe, NM Free Day

Today is at leisure in Santa Fe, a nearly 400-year-old city. Experience the blend of cultures through southwestern architecture. Explore options like a ride to Taos or a sunrise hot air balloon ride for a taste of Santa Fe's diverse offerings.

Overnight: Santa Fe. Breakfast included

Day 9

Santa Fe, NM – Gallup, NM (271 mi)

This morning, journey south to Albuquerque, New Mexico’s largest city, at the heart of the state. Cross the Rio Grande, head west into the Navajo wilderness, pass through Laguna, Grants, and Cibola National Forest. Reach the famous Route 66 town of Gallup for a stay in a biker-friendly hotel with fellow riders from around the world.

Overnight: Gallup. Breakfast included

Day 10

Gallup, NM – Grand Canyon, AZ (283 miles)

Today brings spectacular scenery and iconic Route 66 stops. Cross into Arizona, explore Petrified Forest National Park, and witness a fossilized prehistoric forest. Journey to the Wigwam Hotel in Holbrook, stand on the corner in Winslow, and continue to the Grand Canyon's South Rim for a dream-like evening with a sunset view.

Overnight: Grand Canyon. Breakfast included

Day 11

Grand Canyon, AZ – Laughlin, NV (256 miles)

Experience a "Bird's Eye View" of the Grand Canyon with a morning helicopter ride. Resume Route 66 in Williams, visit Seligman, Hackberry, Kingman, and Oatman before reaching our Laughlin hotel along the Colorado River.

Overnight: Laughlin. Breakfast included

Day 12

Laughlin, NV – Las Vegas, NV (129 miles)

Today, enjoy a quick ride for a detour to Las Vegas, experiencing the Mojave Desert and crossing the Hoover Dam. Though brief, make your time in Vegas sweet, and prepare for resuming Route 66 tomorrow where you left off.

Overnight: Las Vegas. Breakfast included

Day 13

Las Vegas, NV – Victorville, CA (282 miles)

This morning, cross into California, marking the final state on Route 66. Traverse the dramatic Mojave Desert, experiencing the historic route's unique scenery. Explore "waystations" in Amboy and Ludlow, imagining the journey of early Route 66 travellers. Celebrate the last night on the Mother Road tonight.

Overnight: Victorville. Breakfast included

Day 14

Victorville, CA – Los Angeles, CA (124 miles)

Embark on the final leg to Santa Monica Pier, riding the scenic 66 miles of Angeles Crest Highway through Angeles National Forest. Descend into the Los Angeles Basin and reach the Pacific Ocean. At the Santa Monica Pier's "End of the Trail" sign, experience mixed emotions of joy and elation for completing the dream journey and sadness as the ride concludes. Drop your bike off before celebrating the miles and friendships at the Farewell Dinner tonight.

Overnight: Los Angeles. Breakfast and Farewell Dinner included

Day 15

Los Angeles, CA

Today your exciting trip will conclude in Los Angeles. If you need an extra night or two in Los Angeles let us know. Otherwise, make your way independently to the airport.


  • International return flights
  • Accommodation in 3 - 4 Star Motorcycle Friendly Hotels for 14 nights
  • 1 Harley-Davidson motorcycle for 2 people sharing*. Separate motorcycles available at an additional supplement.
  • Late model motorcycle rental, Bike Model Guarantee, Fuel on Riding Days
  • Half-Shell Helmet for Rider and Pillion, Custom Armoured Riding Jacket, Custom Tour Completion Patch
  • Breakfast on Riding Days, Hosted Welcome Dinner on first night, hosted Farewell Dinner and Party on last night
  • Experienced Multilingual Tour Guide
  • Support Vehicle Equipped for Luggage and Spare Bike, Support Vehicle Driver, Door to Door Luggage Service
  • EagleRider On-Road Concierge
  • National Park Entrance Fees
  • Grand Canyon Helicopter Tour on Day 11
  • Hotel Parking Fees, Toll fees
  • Transportation between Tour Hotel and Eagle Rider Locations
  • + VIP Zero Damage Waiver

What's Not Included:

  • Airport transfers
  • Meals unless stated
  • Pre and post nights

*Clients MUST have a motorcycle license to ride

Katie Guy
Book today

Talk to our travel experts for more information and to book or tailor-make your holiday

01 6649900 Call us 9am-7pm Mon-Fri / 9am-5pm Sat-Sun

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