Route 66: Motorcycle Group Guided Tour

14 night trip cruising Route 66 on a Harley Davidson® in a group guided tour

With  your group and experienced tour guide you will cruise Main Street of America all the way from Chicago to Los Angeles. This guided tour will take you along Route 66 through 9 US states and includes cities such as St Louis, Oklahoma City and Amarillo with side trips to the amazing Grand Canyon and Las Vegas before heading to Santa Monica Pier in Los Angeles.

You will join a group for this fixed itinerary. However we can add additional nights in Chicago, Los Angeles or even the Pacific Coast Highway for you to extend your trip.

Includes flights from UK, Harley Davidson® Motorbike hire & accommodation
Fly into Chicago and out of Los Angeles
You’ll ride approximately 2800 miles in total
 Includes St Louis, Oklahoma City, Grand Canyon & Las Vegas
Extra days can easily be added before or after the tour
Your full road trip pack and itinerary will be sent to you
Your entire package is ATOL protected
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Your Itinerary

route 66 chicago
Day 1:
Begin in Chicago

Welcome to the Windy City! Chicago is the biggest and most exciting of the Great Lake cities. It includes a stunning skyline along Lake Michigan, top-rated museums, and restaurants and innumerable bars and nightclubs that pay homage to the city’s strong jazz and blues heritage. Tonight you will get to meet your fellow riders and Tour Guides at the tour hotel, followed by a great Welcome Dinner to kick-off your Route 66 journey!

Fly into Chicago
 Chicago, IL
route 66 springfield
Day 2:
Birthplace of Route 66

This morning you pick up your bike and are off on the ultimate American road trip. From Chicago we head south along the Pontiac Trail, the original name for this bit of the road here, passing through Joliet, checking out the Launching Pad Giant, stopping at the amazing RT 66 Museum in Pontiac and generally getting a feel for the rubber on the Mother Road.

 Approx 200 miles
Springfield, IL
route 66 illinois
Day 3:
Gateway to the West

Enjoy the short ride today into the "Gateway to the West," St. Louis. We will stay primarily on the 2-lane sections of the Mother Road passing cornfields and small towns that represent the heartland of America. St Louis rests along the shores of the mighty Mississippi River and is home to some of the best live music and BBQ ribs in the country.

Approx 190 miles
St Louis, MO
route 66 oklahoma
Day 4:
Joplin

Try to get up early to enjoy the view of the St. Louis Arch and Mississippi River before we hit the road. We quickly leave the city in mirrors as we settle in to enjoy the rolling Missouri hills that make this area so beautiful and fun to ride in. We will stop and see the famous World’s Largest Rocking Chair in Fanning, wind our way on the twisting roads of Devil’s Elbow, and stop at other Route 66 icons. Tonight we will enjoy a stay in Joplin,

 Approx 335 miles
Joplin, MO

route 66 winslow
Day 5:
Into Oklahoma

From Joplin we head west through the hills and horse country of Oklahoma and the reservations of several Native American tribes. This evening we will stay in Oklahoma City, the heart and soul of Route 66! At night you can enjoy at Bricktown, the neighbourhood in the heart of the city full of lively restaurants, bars and shops.

Approx 170 miles
 Oklahoma City, OK
route 66 cadillac ranch
Day 6:
Texas Panhandle

This morning we travel along some of the oldest stretches of Oklahoma’s Route 66.  We will ride along a section of the Chisholm Trial, which passes through Yukon and El Reno, and stop at the amazing Route 66 Museum in Clinton. After lunch we cross the border into the Texas Panhandle, the southernmost portion of the Great Plains. At the Big Texan Steakhouse in Amarillo you have the opportunity to enjoy the best steaks in Texas, guaranteed!

Approx 260 miles
Amarillo, TX
route 66 blue swallow
Days 7-8:
Half way point

After passing through the world famous Cadillac Ranch, we'll stop at the midway point of RT 66 in Adrian, Texas! And how about the ghost town of Glen Rio, where you can stand with one foot in New Mexico and the other one in Texas? Santa Fe is one of America’s oldest and most beautiful cities, and will be our base for the next two nights.  Day two is at leisure to rest and enjoy the distinctive flavour of this nearly 400-year-old city. 

Approx 300 miles
 Santa Fe, NM
 2 Nights
route 66 petrified forest
Day 9:
New Mexico

This morning you head south, down to Albuquerque, the heart of New Mexico, where the main east - west road and rail routes cross both the Rio Grande and the old road south to Mexico. You cross the Rio Grande and head west – out into the open country and the hues of the Navajo wilderness. Enjoy your stay tonight with a host of fellow riders from around the world at one of the many biker friendly hotels in Gallup. 

Approx 270 miles
 Gallup, NM
route 66 winslow
Day 10:
Grand Canyon

Today we cross into Arizona and past Petrified Forest National Park, a fossilized prehistoric forest of gigantic trees that has been unearthed by erosion. Further west is the Wigwam Hotel in Holbrook, and we’ll stop to stand on the corner in Winslow! We will spend the night just one mile from the South Rim of the Grand Canyon! Tonight you will sit with a cold drink in your hand and enjoy the sunset over the South Rim of the Grand Canyon.

Approx 285 miles
 Grand Canyon, AZ
route 66 cadillac ranch
Day 11:
Laughlin

For those looking to get a real "Bird's Eye View" of the Grand Canyon be sure to let us know and we will arrange a morning helicopter ride over the heart of the South Rim. Leaving the Grand Canyon, we will pick Route 66 back up in Williams, Arizona before heading to stops in the famous 66 towns of Seligman, Hackberry and Kingman, and Oatman before arriving at our Laughlin hotel on the shores of the Colorado River.

Approx 255 miles
 Laughlin, NV
route 66 blue swallow
Day 12:
Viva Las Vegas!

Today is a quick ride for a little detour to take in the incredible sights and sounds of Las Vegas! Our journey this morning will take us through our first real taste of the Mojave Desert, and a ride across the famous Hoover Dam! One thing is for sure, your time in Vegas may be short, but it will sure be sweet! Try to get a little bit of sleep because we pick up Route 66 tomorrow right where we left off yesterday.

Approx 130 miles
 Las Vegas, NV
route 66 petrified forest
Day 13:
Mohave Desert

Today we cross the border into our final State on Route 66 – California! One thing is for sure - today is a day like no other as we traverse the Mojave Desert. You can imagine what it must have been like for early Route 66 travellers making their way across this huge desert, dotted with Joshua Trees, cactus, volcanic rock and sand as you stop in the tiny "waystations" of Amboy and Ludlow. Tonight, we celebrate our last night on the Mother Road.

Approx 280 miles
 Victorville, CA
route 66 las vegas
Day 14:
End of the Trail

Today we head off for Santa Monica Pier! Riders always have mixed emotions as they stand at the "End of the Trail" sign on the Santa Monica Pier. There is a sense of joy and elation at having completed a journey most people only dream about, and a sense of sadness at the thought of the ride having come to an end. Tonight, we celebrate the miles we’ve ridden and the friends we made as we party together at our Farewell Dinner!

Approx 125 miles
Los Angeles, CA
route 66 santa monica
Day 15:
Last morning in LA

Make the most of your final morning in Los Angeles today. We can recommend a bike ride from Santa Monica Pier to Venice Beach or perhaps you’d like to see the famous Hollywood sign or walk down Rodeo Drive. This evening you’ll catch your flight back to the UK.

Please let us know if you’d like another day or two in Los Angeles before you fly home. We can arrange for car or motorbike rental for the extra days.

 Fly out of Los Angeles
route 66 los angeles
Day 16 
Arrive back in UK

You’ll arrive back in the UK today. Thank you for booking your road trip with RouteTrip USA.

Arrive back in UK
See the Motorcycles
route 66 los angeles

We have a selection of Harley Davidson Motorcycles for you to choose from. Have a look at your choice here.

SEE THE BIkes

Departure Dates

    • 2020 Dates
    • 2 Sept 2020
    • 3 Sept 2020
  • 10 Sept 2020
  • 17 Sept 2020
    24 Sept 2020
    8 Oct 2020
2021 Dates
8 Apr 2021
29 Apr 2021
6 May 2021
13 May 2021
27 May 2021
3 June 2021
24 June 2021
1 July 2021
15 July 2021

  • 29 July 2021
    12 Aug 2021
  • 26 Aug 2021
  • 1 Sept 2021
    2 Sept 2021
    9 Sept 2021
    16 Sept 2021
    23 Sept 2021
    7 Oct 2021
  •  2 People
  •  1 Motorcycle
  •  1 Bed

From £3929 pp

 2 People
 2 Motorcycles
 1 Bed

From £5143 pp

 1 Person
 1 Motorcycle
 1 Bed

From £6538 pp

 Enquire about our Route 66 Motorcycle Group Guided Tour

If you want to enquire about our other motorcycle trips, please click here
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All per person prices (pp) shown on this website are based on two adults sharing. Where hotel ratings are shown, these are US ratings, half stars are rounded up to the next full star. RouteTrip USA and RouteTrip are registered trademarks of RouteTrip USA Ltd. *T&Cs Apply. **Subject to availability. ***Refundable deposit required