Since concluding our Route 66 adventure four months ago, I have continued to remain active on a number of Route 66 forums and Facebook groups. Those groups are full of people planning their own trips on the Mother Road and are always looking for tips and tricks about how to maximize their time.

I figured it might be an interesting idea to review of our trip, from planning through to lessons learned along the way, and consolidate those in a couple of posts so I have something I can link to that can be more in-depth than what the Facebook comment section will allow.

Phase 1: When Can We Go?

There really isn’t too much advice I can give here because this is going to vary from person to person depending on your circumstances. For us, the two biggest factors were work schedules and weather.

Thanks to my employment in a seasonal business, taking a large chunk of time off in the summer simply isn’t possible. I need to wait until the peak of summer travel is done before I can consider taking the time. Emily’s schedule is not nearly so cyclical so she has more flexibility in terms of the time of year.

Frankly, even if we could go in the summer months, I don’t think we would want to. Heading to the southern U.S. in the peak of summer would mean heat — and a lot of heat. On the other hand, we didn’t want to go in the dead of winter either because that would mean cooler temperatures and potentially bad roads, especially in the northern portions of our trip and at the higher elevations.

Once all that was factored in, we chose a departure in the latter half of September. That took us on to Phase Two.

Phase 2: How Long Can We Take?

This is a very common question for people planning a Route 66 trip. Again, there are a number of personal factors to consider. How much vacation time do you have? How long can you be away from work? And, of course, the longer you are on the road the more money it will cost so sometimes the best answer to this question is “How much can you afford to spend?”

After considering everything, we planned to take three weeks away from work to do the trip. We figured we would need two solid days of driving to get to Chicago and three days to drive home from Los Angeles. With those five days factored in, that would leave us 16 days to be on Route 66 itself.

Phase 3: Building the Schedule

My two biggest tools for trip planning are Google Maps and Microsoft Excel. Google Maps serves many purposes. For a year before we started our trip, I would save Pins to a Google Map of places we wanted to see along the way. This way it became a “checklist ” of sorts, making sure we didn’t forget something to include. And, of course, it comes in very handy for distances, drive times, and routing purposes.

Now, planning Route 66 is different than many other trips and Google Maps needs a little massaging to make it work. First, it tries to get you places the fastest way possible, which simply won’t do. For Chicago to Santa Monica, it wanted to route us through Iowa, Nebraska, Colorado, Utah, and Nevada. Nope, nope, nope. Lots to see through those areas, I’m sure, but we need to select the more southern route. Now, it has selected a whole lot of Interstate highways — I-55 from Chicago to St Louis, I-44 from St. Louis to Oklahoma City, I-40 from Oklahoma City to Barstow and then I-15 and a mess of freeways to Santa Monica. It mostly parallels Route 66 so it provides a good distance estimate, which in this case is 2138 miles.

Now for some simple math. 2138 miles divided by 16 days means we need to cover about 135 miles per day on the road. Figuring if we have an average driving speed of 50 MPH, that means a little less of three hours of driving per day, but let’s call it three to be safe. If we want to keep our average time on the road per day around 8-10 hours, that means we have 5-7 hours to see whatever we want along the way. That seems reasonable.

Now I move into building my Excel sheet. I created a bunch of columns, starting with the date on the left, the day of the week next, our starting point, our ending point, number of miles between them, and then a calculated field showing how many hours of driving I expect that to be. I then have further columns for the name of the motel we plan to stop at, our reservation confirmation number, and anything specific we want to see during the course of that day, especially if it is something larger like a museum that will take a bit of time. There simply wouldn’t be enough space to list EVERYTHING we want to see, especially if we were to count every little photo stop.

So, starting from the beginning, I plot out a rough itinerary. Using Google Maps to estimate distances, I build out all 16 days of our trip. At this point I’m not worrying about exactly where each day ends, I’m simply creating a lot of placeholders, roughly 135-150 miles apart — this forms the framework for the trip.

Now, from this point on, it becomes a process of constant refinement.

One of the things we were most interested in seeing were the classic Route 66 motels. We also knew we had certain ones we wanted to stay at such as the WigWam in Holbrook, Arizona, the Blue Swallow in Tucucari, New Mexico, and the Wagon Wheel in Cuba, MO.

We would look at our basic itinerary and see which stop was closest to that motel and then change our end point for that day to the motel we wanted. A quick search on Google Maps (and a lot of creating waypoints in between to force it to stay on Route 66 as much as possible) would give us new distances to plug into the speadsheet.

This process would continue over and over again.

“Hmm, if we want to stay here that means Day 9 is really long so we better change our stop that night to be here instead of here.” “Gee, if we want to have time to see this museum on that day we better not plan on getting all the way to such-and-such town that night.”

We would also factor in the days of the week. “Crap, we pass by the museum on a Sunday but it is closed so if we want to see it we’ll have to reschedule the stop the night before.”

That process would continue, often forcing us to make tough calls and prioritize certain things over others. With a limited amount of time it isn’t possible to do it all.

If there was a certain motel we wanted, we would book it once we had firmed up the dates. Many of the motels are very popular and can get booked up months in advance during tourist season so locking them in is crucial.

We tried to leave as much flexibility in our schedule as possible. We booked the specific motels we really wanted to stay at but didn’t book every night for the whole trip. If we came across something that took longer than expected, we wanted to be able to stop without going as far as planned and still be able to make it up later in the trip. The last thing we wanted was to be two hours from our destination with the sun going down and having to drive like crazy in order to make our reservation.

So, that’s how the plan came together. You can see the results in the YouTube playlist here:

Our Final Schedule

In the end, this is what our trip looked like. I’ll comment on our lessons learned in the next posting.

Day 01: Chicago, Illinois to Springfield, Illinois (210 miles)

Day 02: Springfield to Cuba, Missouri (187 miles)

Day 03: Non-travel day spent in St. Louis

Day 04: Cuba to Springfield, Missouri (179 miles)

Day 05: Springfield to Tulsa, Oklahoma (182 miles)

Day 06: Tulsa to Clinton, Oklahoma (191 miles)

Day 07: Clinton to Amarillo, Texas (176 miles)

Day 08: Amarillo to Tucumcari, New Mexico (113 miles)

Day 09: Tucumcari to Santa Fe, New Mexico (178 miles)

Day 10: Non-travel day in Santa Fe

Day 11: Santa Fe to Gallup, New Mexico (199 miles)

Day 12: Gallup to Holbrook, Arizona (99 miles)

Day 13: Holbrook to Williams, Arizona (121 miles)

Day 14: Williams to Needles, California (177 miles)

Day 15: Needles to Barstow, California (161 miles)

Day 16: Barstow to Santa Monica, California (133 miles)

Total Distance: 2306 miles