Harley-Davidson touring motorcycles parked beneath a giant Route 66 shield mural
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14 nights · Chicago, United States → Los Angeles (Santa Monica Pier), United States · Motorcycle

Route 66 Self-Guided Motorcycle Tour

Route 66, self-guided, start to finish, from Chicago to the Santa Monica Pier, with a free day built in at Santa Fe and a dedicated Grand Canyon day near Williams – fourteen nights across eight states.

Stradora Partner
From£3,430pp
Duration14 days
StyleSelf-guided
Best suited toExperienced riders
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14 nights through United States

Few roads carry as much weight as Route 66, and fewer still can be ridden from the first mile to the last in one trip. This self-guided run covers the whole of it, Chicago to the Santa Monica Pier, around 2,430 miles through Illinois, Missouri, Oklahoma, Texas, New Mexico, Arizona, Nevada and California. Fourteen nights, eight states, and the Mother Road end to end.

Self-guided means the days belong to the rider. The route is planned, the hotels are booked and the bike is ready, but there is no group to keep pace with and nothing in the diary beyond the next town. Riding days sit between roughly 110 and 290 miles, long enough to feel the country change underneath and short enough to stop for whatever looks worth stopping for.

The road does most of the storytelling. The Illinois prairie gives way to the Missouri Ozarks, then Tulsa, the Oklahoma plains and the long flat run into Amarillo. Santa Fe earns a free day for its adobe streets and galleries. Gallup and the red rock country around Flagstaff follow, with a day set aside from Williams for the Grand Canyon, before Laughlin, the Mojave and Victorville lead down to the Pacific.

EAGLERIDER supplies the motorcycle, with a choice of Harley-Davidson touring models or BMW and Yamaha sport-touring machines, and books every night’s accommodation along the way. Fuel, meals and insurance are arranged separately, which keeps the trip flexible and the daily spend in the rider’s own hands. For anyone who has had Route 66 on a list for years, this is the version that does not cut it short.

Style
Self-guided
Duration
A fortnight (11-15 nights)
Region
North America
Vehicle provision
Vehicle provided
Departures
January - December
Starts/ends
Chicago, United States → Los Angeles (Santa Monica Pier), United States
Accommodation
Hotels
Suitable cars
Experienced riders
Vehicle
Motorcycle
Price basis
Per person, two riders with two bikes (operator Package 3), USD 4,543. Operator also prices one rider with one bike at USD 5,820 and two riders sharing one bike at USD 3,077 per person. Read from the operator page 14 Oct 2026.
Run by
Specialist Stradora partner

What's included

  • Not fully confirmed - motorcycle rental (choice of Harley-Davidson touring models or BMW/Yamaha sport-touring models) and nightly hotel accommodation are confirmed
  • the site's 'What's Included' tab did not render via automated access
  • so a full inclusions list needs a manual check

Not included

  • Fuel
  • insurance (offered as optional add-on at checkout)
  • meals
  • taxes and fees

Ready to drive it?

14 days, from £3,430pp

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