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Route 66 starts in Chicago

Historic Route 66 > FAQ > Start planning my Route 66 trip

How do I start planning my Route 66 trip?

The crucial thing to remember is that on a Route 66 trip, Route 66 is your destination. This implies that your destination is not Los Angeles, nor Santa Monica, and neither is Chicago. Your destination is where you are at the moment on Route 66. The mood that comes with that is essential as it allows you to relax and get out of the rat race.

Pick your dates

Plan on doing less than 200 miles per driving day. Ideally, stay below 150 miles unless you're in the Mohave desert.

The first thing to do is to try to find when you'll be having your trip.

Things that can help you with that are:

As mentioned in the "how long" entry above, you might also want to determine if you go for all of Route 66 from Chicago to Los Angeles or only a portion of it. It's highly recommended by those who did 66 before you, that you allow plenty of time! And hence, it's better to do only a part if you are limited in time and keep the rest for another vacation.

While on Route 66 you want to plan less than 200 miles a day, a bit more in the desert and a lot less in greater LA.

Check your dates with possible Route 66 events and US holidays. You can see this as both a reason to try to attend something or avoid the crowds just as well.

Pick your vehicle

We'll assume you're going to do Route 66 in a car, but other options are available as well:

Book it

Now that you have dates and a start and end point, you can start to book

Prepare to stay on Route 66

As roadsigns along Route 66 are by far not reliable enough to guide you onto Route 66:

  • You need a good guidebook. The EZ66 guide is widely seen as the best option, many even call it their bible while on the road. Get it up front as you want to become familiar with it before you're on the road.
  • Many want a map of Route 66 as well. The 8 map set is your best choice.
  • If you prefer an app on your phone, the Route 66 Navigation app is unique in its ability to do offline navigation onto Route 66.
  • If you have a GPS (satnav) with US maps on it: take it along, but don't bother with trying to use it for guiding you onto Route 66, they're horrible at it.

Take care with side trips

We see lots of people who try to cram in as much as possible. But there is a price to pay if you do that. The cost is double: side trips bring you out of the mood of being at your destination all the time, and they eat up a whole lot of your time. If you can, plan this to be optional, so that you can skip the side trip if you run out of time too much by the time you get there.

Also, be extra careful not to skip vast portions of Route 66 by making a side trip.

Where do I stay for the night?

You can reserve rooms via booking.com(*)

To find the area, you need to figure out where you will be. If you plan this up front, make sure to make daily progress and maximize the number of driving days. Don't solely aim for the big cities, they often have less of the Route 66 feeling. You'll find that atmosphere more readily in a smaller town.

Once you have the area, you need to find the motel that's right for you.

What are the must stops?

It's a Route 66 trip, so above all make sure not to miss the old road itself (hence the guide above).

The problem with the concept is that these must stop lists cannot be made complete. There are literally tens of thousands of possible reasons to stop, take pictures, enter a business, talk to people, … that a complete list isn't going to happen. Moreover, these potential stops cater to different needs and interests. If you look around, you'll find multiple of these lists, but you'll be adapting your plans to their interests and bias (if any).

It's simply better to drive the old road and see what you encounter:

  • If that's an old abandoned building not featured on any list: have fun taking that picture.
  • If it's a new business you see: enjoy it.
  • If it's an icon of the road, your EZ66 guide, app, or whatever you use will already have it and point you to it.

Many feel that staying at the iconic motels and eating in the mom-and-pop places is an integral part of the experience of traveling Route 66.

Do some research for yourself

Try to learn a bit about Route 66, its history and about what you will encounter. Even if you merely read the EZ66 guide up front, it will prepare you for your trip already. But there are plenty of other excellent Route 66 books to help you become ready for your trip as well.

The goal of this study is not just to know what to expect. It is also to have some background stories so that it all becomes easier to grasp. The more important reason might well be to have an idea of what you'll encounter and enable you once on-site to balance on what type of roadside stops you want to spend more time and which other stops you'll just drive past or stop for a quick photo.

Part of this preparation is also to make sure to align your interests with your travel partners. There is a wide range of things you can spend a limited supply of time on while on Route 66. It's best to make some compromises up front and not waste time on arguments while on the road.

If you have kids with you who are interested in the Disney/Pixar movie "CARS", there is a lot of what inspired the movie to be found all along the road.

Do not over plan

It's entirely possible to plan your Route 66 trip in too much detail. Leave some room to be surprised by something, to stop on a whim, to some freedom, and be a little bit of a rebel.

International tourists

  • Have a passport that's valid for long enough.
  • If you qualify for the visa waiver program, complete your ESTA. Only use the official site! Otherwise apply for a visa though a US embassy.
  • Should you use a travel agent? Sometimes they can help you find a good deal on flights and rental cars, but if you persist a bit, you can find it yourself just as well. Whatever you do, do not let them talk you into a trip where you only stay in major cities and have days where you need to drive 300 miles or more. You'll have to revert to the Interstate and will miss all of Route 66. Most experienced Route 66 travelers will avoid the travel agents for booking their overnight stays beyond the first night as they typically can't make bookings at the more iconic motels and often don't understand the need to slow down and maximize the number of driving days vs. staying longer in the bigger cities.
  • Make sure to bring one or more credit cards with a decent spending limit, you'll need it. How to pay for things.
  • If you lack experience driving in the US, there are some things to learn about driving in the USA.
  • Take care with roaming your GSM, esp. the rates some operators back home will charge you for mobile Internet connectivity while in the USA can be outrageously high.
  • Make sure to bring things like power plug converters as those you need are hard to find along Route 66.

There is more help in our other FAQ entries. If you have additional questions or seek further explanation, don't hesitate to join our Facebook Group and ask there.

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