Riding Route 66 means crossing the United States on one of the world's most legendary roads. From Chicago to Los Angeles, the Mother Road stretches for almost 4,000 kilometres through diners, historic motels, vintage filling stations, small towns, wide-open spaces and the landscapes of the American West.
But there is a long way between dreaming of Route 66 and planning the trip itself. Which itinerary should you choose? How many days do you need? Should you follow every surviving historic section? Where should you stay? Which motorcycle should you rent? Should you travel with a group or independently? Most importantly, how do you avoid missing the sections that make the Mother Road special?
Working with a Route 66 travel agency turns that idea into a real road trip without spending weeks organising every detail. At Planet Ride, we have been designing motorcycle Route 66 road trips for more than ten years, with one simple principle: there is no single right way to experience this myth. Choose a guided tour, an independent trip or a fully tailor-made itinerary.
Why use a travel agency for Route 66?
Planning your own Route 66 trip is certainly possible. The challenge, however, is not simply booking hotels between Chicago and Los Angeles.
The historic Route 66 no longer exists as one continuous official road. Some sections have disappeared, others run alongside Interstates, and the most rewarding stretches are not always the easiest to find. A coherent itinerary has to account for daily distances, accommodation, vehicle rental and the practical constraints of a multi-day trip in the United States.
A Route 66 specialist travel agency centralises that work and gives you an itinerary designed by road-trip experts. Planet Ride does more than reserve a trip: we build a route that lets you enjoy Route 66 without turning its preparation into a second full-time job.
How to choose a travel agency for a Route 66 trip
When choosing a Route 66 travel agency, look beyond the headline price. Good local knowledge matters: American distances are substantial, and a stage that looks reasonable on a map can become a long day once sightseeing stops and detours are included.
Your travel agency should be able to advise you on:
- the Route 66 itinerary and its key stages;
- the right trip duration;
- accommodation and motorcycle or vehicle rental;
- daily distances and historic sections worth prioritising;
- visits, experiences, American West extensions and local support.
Planet Ride specialises in road trips and itinerant travel. We offer several ways to experience Route 66, depending on how independently you want to travel.
Riding Route 66 by motorcycle: the classic American road trip
For many riders, Route 66 by motorcycle is the trip of a lifetime: Chicago, St. Louis, Tulsa, Amarillo, Santa Fe, Albuquerque, Flagstaff and Los Angeles. Between those major stops lie miles of asphalt, neon signs, diners, historic filling stations, towns that seem frozen in another era and the distinctive feeling of crossing America from east to west.
A Route 66 motorcycle trip is also a logistical adventure. You need a suitable bike, realistic stages, manageable luggage, a plan for long distances and a clear understanding of how riding in the United States works. You may choose a Harley-Davidson or another model depending on availability and your riding style.
The aim is for the motorcycle to be part of the journey, not for its logistics to become the main constraint.
How long does Route 66 take?
The ideal duration depends on how you want to travel. To connect Chicago and Los Angeles along Route 66, allow at least around two weeks for a coherent road trip. But Route 66 is not about accumulating miles.
The value of the trip is in the stops: walking into an old diner, photographing an abandoned filling station, talking with a local resident or taking a surviving section of the Mother Road. With more time, you can slow down and add detours to major American landmarks. The best itinerary is not necessarily the fastest one; it is the one that leaves you time to experience the road.
What budget should you allow for a Route 66 trip?
The price of a Route 66 trip depends greatly on the format you choose. Duration, departure period, vehicle or motorcycle type, accommodation category, insurance, activities and level of support can all change the budget significantly.
A guided Route 66 motorcycle tour does not include the same services as an independent road trip. Planet Ride offers several Route 66 formats with different service levels and can also design a tailor-made stay.
Why plan your Route 66 trip with Planet Ride?
Because we do not simply sell a sequence of hotels and a motorcycle rental. Planet Ride specialises in itinerant travel and road trips. For more than ten years, our teams have supported riders and travellers on American roads, building itineraries for people who see the road as much a part of the journey as the destination.
By motorcycle, as a couple, with friends or as part of a group, the project remains the same: cross the United States on the road whose sign you have probably seen hundreds of times before putting your own wheels on it. All that remains is to write your own version of Route 66.