Getting started planning your Route 66 itinerary can be a daunting task. Do you begin with a wishlist of sights and attractions or the knowledge of where you'll be spending each night? Do you book your accommodation in advance or do you go with the flow? How long does it take? Will I miss anything?
Things can get stressful really quickly if you let it, so take a deep breath and remind yourself that this is supposed to be fun!
The good news is that there are answers to all of the questions above. The bad news is that they'll be different depending on who you ask! There's no right or wrong way to go about this but there are a couple of common questions that you'll need to ask yourself before you delve into the details: how much time can you spare and what is your budget? I can offer guidance on the first but only you can answer the second.
When it comes to the time you can spare, if you're considering traveling the full length of the route, then you should allow for at least two weeks. You can find further guidance here on how long your trip might take. Anything less than two weeks and you risk rushing through without being able to truly enjoy the experience.
When armed with the answers to these two questions planning a Route 66 itinerary becomes a far less daunting task. As long as you are able to break the task down into smaller manageable chunks, then planning a trip like this is great fun. For me it just added to the whole experience - months were spent reading blog posts and scanning forums, getting more and more excited as it got closer and closer. I even mapped my route and overnight stops using pins on a huge map of the US on my living room wall!
Now that you know how long you will be spending on this trip it’s time to start penciling in some ideas for where you will be spending each night. I'd recommend going about it this way so that you can plan for a (roughly) even daily mileage. Many people like to spend a night or two in Chicago first (assuming you're heading west) and the same when they reach LA so take that into account. Buy yourself a good sized map of the US and use it to approximate where you'll spend each night, trying to keep roughly equal distances between each stop. You're not committing to anything - just trying to establish a broad idea of where you may reach each evening. Be realistic and make sure that there’s not too far between each stop that’ll not allow you to see what you want to see.
A further consideration might be whether you intend to do any side trips or not (Grand Canyon, Las Vegas, etc...). If this is the case then time should be allowed within your itinerary to allow for the extra travel. A day or more for each would be about right. You can use this guide to the five most popular side side trips to help you decide.
Now that you have a broad idea of where you might end up each day there may be some motels in that area that you feel you would like to book in advance. If so then make a note of them. If you decide not to book any accommodation in advance then you can just make a note of the general area you hope to arrive at each day. You can find more advice on whether to book in advance or "wing it" here.
One of the most commonly asked questions on the Driving Route 66 forum or Facebook page is "what are the best Route 66 motels?" This isn't an easy question as it depends upon what you're looking for - creature comforts, authenticity, or to fit within a certain budget. Also, beauty of driving Route 66 is traveling the road less followed and discovering your own hidden gems. However, if you're looking for guidance on some of the more iconic stops then it's worth checking out my Highly Recommended Route 66 Motels Part 1 and Part 2. Personally I'd recommend a mixture of pre-booked motels and those you'll discover for yourself. Personally, I booked every third night in advance to help me keep on track and to make sure I got to spend the night in some of the more iconic lodging. You should find that you’ll soon have a list of definite motels and potential areas to stop-over spread fairly evenly across your journey.
It’s not uncommon to leave your motel at 9am and not reach your next evening's lodging until 5pm but that’s not to say you’re driving for the whole time (in fact you might have only covered 200 miles!) The special thing about Route 66 is that you’ll find yourself stopping off every so often even if just for 10 mins to stretch your legs or stop at a diner for a coffee. Then of course you have the many towns, museums, gift shops and other sights to experience so 200 miles can easily take a full day. Also, aside from the places you’ve read about, or are included in the EZ Guide, you’ll find your own spots to stop at even if it’s just to take photos or buy a postcard to support a local business.
You might find the Trip Planner on this website useful as you are not only able to filter sights and attractions by state, but also display them in order from east to west or west to east. Alternatively you can check out the guides to the various states here: Illinois, Missouri, Kansas, Oklahoma, Texas, New Mexico, Arizona, California. In addition to these resources try to keep in mind that there's no definitive list of things you have to see on Route 66 and that a great road trip is about exploring and finding things for yourself.
If it helps, you might want to note down some sights and attractions that you'll have the option of exploring each day, but unless there's something you're particularly excited about I'd be inclined to just go with the flow. Plan your trip as you go rather than try to create an itinerary that accounts for every hour of every day. Spending the evening reflecting on your day's travel, and reading up on the following day's possibilities, is all part of the fun!