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The Great American Road: A Harley-Davidson Odyssey Along Route 66

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Price available on enquiry

More information available upon request. Minimum duration may apply.
Please read our terms and conditions before booking.

Ten days of open-road freedom, heritage, and timeless Americana — a guided expedition tracing the legendary Route 66 from its birthplace in Chicago to the sun-drenched shores of California.

Your adventure begins in Milwaukee — the heartland of Harley-Davidson. Spend two nights immersed in the brand’s storied legacy, exploring the iconic Museum and seeing firsthand where it all began: the humble shed where Mr. Harley and the Davidson brothers built their first motorcycle.

About This Experience

From there, the journey unfolds across eight states, along the “Main Street of America,” through deserts, small towns, and sweeping plains that embody the soul of the United States.

Each stretch of road reveals a new facet of freedom — the neon glow of Route 66 diners, the red rocks of Arizona, the bright pulse of Las Vegas, and finally, the vast Pacific beckoning at Santa Monica Pier.

Highlights Include

  • Guided Route 66 Expedition
    Traverse 1,620 miles / 2,592 km of one of the world’s most famous highways, led by expert tour captains and supported by a dedicated crew.

  • Exclusive Harley-Davidson Museum Access
    Begin your odyssey with private entry to the Harley-Davidson Museum, celebrating over a century of innovation, craftsmanship, and rebellion.

  • Scenic & Cultural Stops Along the Route
    Ride through small-town America — from the classic motels of Illinois to the ghost towns of the Mojave Desert. Experience curated local encounters, iconic roadside landmarks, and breathtaking national parks.

  • Custom Motorcycle Selection
    Choose from a fleet of premium touring and sport models, including the Street Glide, Road Glide, Heritage Softail Classic, or BMW R nineT — each offering power, precision, and comfort for the journey ahead.

What’s Included

  • Late-model motorcycle rental

  • 3–4 star motorcycle-friendly accommodations

  • Fuel on riding days

  • Custom armored riding jacket

  • Breakfast on riding days

  • Hosted welcome dinner and legendary farewell celebration

  • Half-shell helmets for rider and passenger

  • Experienced multilingual tour guides

  • Support vehicle with luggage service and spare bike

  • Door-to-door luggage assistance

  • Dedicated on-road concierge

  • National park and toll fees

  • Hotel parking and transfers between tour hotel and departure point

  • Custom Route 66 tour completion patch

Good to Know

To join this guided adventure, riders must:

  • Be 21 years or older

  • Hold a valid, unrestricted motorcycle license

  • Have a valid credit card for registration

Accommodations reflect the rhythm of the road — a blend of luxury, nostalgia, and authenticity. One night may be spent in a four-star Chicago hotel, another in a vintage Route 66 motel, and another still in a mountainside lodge or vibrant Las Vegas resort.

A detailed packing list and welcome packet will be provided prior to departure to ensure you’re fully prepared for the ride of a lifetime.

Who This Experience Is For

For the modern explorer who craves both power and poetry — who feels most alive with wind on their face and endless road ahead. This journey is a tribute to freedom, legacy, and the thrill of discovery.

Price available on enquiry

More information available upon request. Minimum duration may apply.
Please read our terms and conditions before booking.

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