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16 nights · Milwaukee, United States → Los Angeles, United States · Motorcycle

Route 66 Motorcycle Tour - Harley-Davidson VIP Experience (Guided)

Start with a VIP experience at Harley-Davidson’s own museum, then join the full guided Route 66 group in Chicago for the entire road to Los Angeles – sixteen nights of complete guided coverage.

Stradora Partner
From£6,591pp
Duration16 days
StyleGuided
Best suited toExperienced riders
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16 nights through United States

The most complete, and the most expensive, trip in the EAGLERIDER range. Seventeen days, sixteen nights and around 2,900 miles, opening with a VIP day at the Harley-Davidson Museum in Milwaukee before joining the full guided Route 66 run from Chicago to the Santa Monica Pier.

The Milwaukee experience is the part nothing else offers, and places are strictly limited each year. It goes well beyond the public museum visit, into the archive and the collection that includes Serial Number One, the oldest surviving Harley-Davidson. A short 93-mile ride along the shore of Lake Michigan then reaches Chicago, where the tour meets the standard guided group and the Mother Road itself begins.

What follows is Route 66 in full and led throughout. Springfield, St Louis, the World’s Largest Rocking Chair, Devil’s Elbow, the Blue Whale at Catoosa, Tulsa, Oklahoma City and the long haul to Amarillo, then two nights and a free day at Santa Fe. Gallup, the Petrified Forest and Winslow lead to the Grand Canyon, with a helicopter flight offered, then Seligman, Kingman and Oatman, the Hoover Dam, Las Vegas and the Mojave into Los Angeles.

EAGLERIDER provides the motorcycle, the tour leader, all sixteen nights, the museum experience and the group dinners. Fuel, most meals and insurance are arranged separately. For a rider treating Route 66 as a once-in-a-lifetime trip, and who wants to start where the machines are actually built rather than at the city limits, this is the flagship of the whole range, and it is priced accordingly.

Style
Guided
Duration
Grand tour (16+ nights)
Region
North America
Vehicle provision
Vehicle provided
Departures
May
Starts/ends
Milwaukee, United States → Los Angeles, United States
Support
Guide
Accommodation
Hotels
Suitable cars
Experienced riders
Vehicle
Motorcycle
Price basis
Per person, two riders with two bikes (operator Package 3), USD 8,731. Operator also prices one rider with one bike at USD 11,003 and two riders sharing one bike at USD 6,549 per person. Read from the operator page 14 Oct 2026.
Run by
Specialist Stradora partner

What's included

  • Guided group with tour leaders
  • motorcycle rental
  • nightly hotel accommodation
  • VIP Harley-Davidson Museum experience
  • farewell dinner
  • optional Grand Canyon helicopter flight
  • full inclusions list needs manual check

Not included

  • Fuel
  • insurance (optional add-on)
  • most meals
  • taxes and fees

Ready to drive it?

16 days, from £6,591pp

Stradora Partner
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