Planning One Day in a City

One of the biggest challenges we faced on our trip was the lack of time to really “take in” any one place. Of course, we knew that would be the case when we decided to do such an intense road trip, but we still wanted to make the most of our stopovers. 

Cities were especially difficult. What was the point in visiting a city for just one day — what could we possibly discover in such a short time? With thousands of things to do, attractions to visit, restaurants to eat in, and neighborhoods to explore, it seemed impossible to select only one or two activities. Even deciding what neighborhood to stay in required research and led to long discussions of the relative merits of locations we knew nothing about.

As we developed our itinerary we made the radical (for us) decision NOT to stopover in any of the big cities along the route — apart from Chicago and Los Angeles, that is. We chose to spend time in these two cities because they were respectively the start and the end of Route 66 — and as such, important points of emphasis. Otherwise, we would skip the cities, reasoning that we were urban creatures, and could discover more by staying away from our familiar environments and engaging with “small town America” as much as possible. 

Still, we had Chicago and L.A. to plan for, and only a day or two in each (eventually as we fleshed out the rest of our trip we would add Las Vegas and New Orleans to the itinerary, too).


There was another issue we would have to work out if we wanted to enjoy these quick urban visits. We would have to confront our aversion to doing “tourist” things. For years, both “Cactus Killer” and I have avoided most kinds of ultra-touristic activities (largely because most of our travels are not tourism-related, but also because we are typically in search of some specific “insight” into a place, however arcane), but this trip would be different.

A road trip by its very nature is “touristic.” You cannot hope to actually gain any deeply meaningful perceptions about a single place — it is more the patchwork of all the little bits you find along the way that form into an amazing whole. And, let’s face it, the simple fact that you are going from “site” to “site” makes you a tourist whether you want to call yourself that or not.

So “enlightened tourism” would be the buzz word. We would have to just get over ourselves and accept the label.


The game plan would be to organize one “activity” in each city. That kept us open to the possibility of serendipitous encounters, while still ensuring that we did something that would leave us with a unique impression of the location.

We tried to chose something off-beat (at least to us) that reflected the specificity of each city. We were also determined that each planned “activity” should provide a fun opportunity for us to learn something new. Finally, we did our best to “mix it up,” varying adventure challenges, performances, historical attractions, and outdoor activities, with a few museums and “tours” thrown in for good measure.

Here is the criteria we used:

1. Dare to Be Silly. Sometimes you might have to accept feeling a bit ridiculous, playing along with a “theme” tour or performance. Do it anyway. You’ll laugh harder and make much better memories!

2. Take the Challenge. Do something you have never done before. Try something you have always wanted to do. The experience will be unforgettable. And when you’re done you get to say, “Wow! I did that!”

3. Do It Yourself. Learn to be the pilot, not just a passenger. Choose to “do” things yourself — even if it means taking a “beginner’s” skydiving lesson instead of a “tandem” flight. You will feel it more intensely and perhaps you will discover a new passion!

4. Have Fun! (no explanation necessary)

And, in case you are curious, here are a few of the “activities” we did on our trip: 1920s gangster tour and show in Chicago; rafting solo on the Meramec river; “Texas” the musical performed outdoors in a canyon; hiking the dunes in the Mojave desert; beginner hang gliding lessons in L.A.; Alcatraz evening tour; off-roading in Death Valley; shooting machine guns at a Las Vegas range; hiking two days in a river at the Zion Narrows; rappelling through waterfalls in Moab; rafting through the rock slide on the Rio Grande; Cajun music jam on the back porch of a roadhouse; swamp tour on the Atchafalya Basin; and so much more…

Read more on how we planned our day in Chicago: DAY 3: CHICAGO, HAVING FUN WITH HISTORY

2 Responses to “Planning One Day in a City”

  1. Rick Schmidt says:

    Just found your website about your trip (from your posting on Amazon’s travel pages) and I’m looking forward to reading all of it.
    Planning a cross-country road trip myself, from San Diego to Washington, but still need a companion to keep boredom at bay and just for safety reasons like you stated.
    Planning it for fall of this year.
    Got any suggestions on how to find a travel buddy?

    Well, thanks very much for your website.

    Rick Schmidt

  2. Blue Coyote says:

    Rick, am hoping your trip will be GREAT! (am assuming you are talking san diego to washington dc and not washington state) in any case, finding a good travel buddy can be hard, because sometimes even your best friend isn’t quite interested in the same travel style or itinerary… in our case we were lucky, as we are long time friends who have travelled together in all sorts of circumstances so it was natural that we would plan this kind of trip… the most important suggestion i have is to look among your friends and acquaintances for someone who is interested in the same style of travel… that is really key… and if possible try a short trip together before the big cross country drive… just to make sure you don’t get on each others nerves or hate each others choice of music!

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