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 Route 66: Motorcycle Group Guided Tour

16 day 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

deep south road trip

Day 1:
Chicago

Chicago, the Windy City is the biggest and most exciting of the Great Lake cities. It has 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 with a great Welcome Dinner!

Fly into
Chicago

Chicago,
IL

route 66 springfield

Day 2:
Springfield

This morning you'll pick up your bike for the ultimate American road trip. We'll 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 Route 66 Museum in Pontiac and generally getting a feel for the rubber on the Mother Road.

Collect
Motorbike

200
miles

Springfield,
IL

route 66 illinois

Day 3:
St Louis

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.

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  leave the city and enjoy the rolling Missouri hills that make this area so beautiful and fun to ride in. We will wind our way on the twisting roads of Devil’s Elbow, and stop at several Route 66 icons. Tonight we will enjoy a stay in Joplin,

335
miles

Joplin,
MO

deep south road trip

Day 5:
Oklahoma City

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.

170
miles

Oklahoma City,
OK

route 66 cadillac ranch

Day 6:
Amarillo

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 after lunch we cross the border into the Texas Panhandle. At the Big Texan Steakhouse in Amarillo you have the opportunity to enjoy the best steaks in Texas, guaranteed!

260
miles

Amarillo,
TX

route 66 blue swallow

Days 7 - 8:
Santa Fe (2 nights)

After passing the world famous Cadillac Ranch, we'll stop at the midway point of '66 in Adrian, Texas and then the ghost town of Glenrio, where you can stand with one foot in New Mexico and the other one in Texas! Our next two night will be in Santa Fe, one of America’s oldest. Day two is to rest and enjoy this nearly 400-year-old city.

300
miles

Santa Fe,
NM

route 66 petrified forest

Day 9:
Gallup

This morning we head south to Albuquerque, the heart of New Mexico. We'll 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.

270
miles

Gallup,
NM

route 66 winslow

Day 10:
Grand Canyon

Today we cross into Arizona and past Petrified Forest National Park. 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.

285
miles

Grand
Canyon, AZ

route 66 cadillac ranch

Day 11:
Laughlin

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.

255
miles

Laughlin,
NV

route 66 blue swallow

Day 12:
Las Vegas

Today is a little detour to take in the incredible 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.

130
miles

Las Vegas,
NV

route 66 petrified forest

Day 13:
Victorville

Today we cross 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. Tonight, we celebrate our last night on the Mother Road.

280
miles

Victorville,
CA

route 66 las vegas

Day 14:
Los Angeles

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

125
miles

Los Angeles,
CA

route 66 santa monica

Days 15 & 16:
Last Day & Fly Home

Make the most of your final morning in Los Angeles today. Maybe 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. 

Return
Motorbike

Fly
Home

route 66 santa monica

Want extra days in
Chicago or California?

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

route 66 los angeles

See our choice
of Motorcycles


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

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

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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. ***On request, subject to availability and refundable deposit required