What is the single hardest part of planning an epic road trip?

Choosing where to go. SERIOUSLY. This is a big deal. If you choose the wrong destinations then your entire trip will be ruined forever and ever and you'll never want to take another road trip and you'll barely even be able to get into a car because it will be a reminder of all the things you didn't do that you wanted to, and did that you didn't want to.

If you don't do this right, if you don't choose your road trip destinations wisely, you'll feel like the ultimate failure.

This is a BIG DEAL.

Just kidding! I've been on a few road trips. None of them were perfect, yet all of them gave me experiences and memories that I'll remember, and cherish, forever. When it comes to choosing where to stop along the way there are very few wrong answers, and a whole world of right ones.

Earlier this year my husband and I embarked on a 31-day adventure from the Chicago area to San Diego and back. It was an epic road trip and we saw some mind-boggling and incredible parts of the country. Next year, we're going to do it again, but we'll explore a whole different section of America.

One of the things I learned planning this last road trip was how to choose our destinations. It's not easy when you want to go EVERYWHERE, but I was able to narrow it down to something that was (somewhat) manageable. 

How did we do that, you ask? Read on, fellow traveler, for my tips on how to choose your road trip destinations.

Step 1: Set a Time Limit

The very first step is figuring out how much time you've got for this road trip. A month-long trip is a whole different beast than a weekend tour. For example, when we go camping for a weekend, we don't want to drive more than about three hours, so that gives us a specific radius. If you've got more time, you can obviously go further.

Our epic Southwestern America road trip of 2017 began with a time limit of a month, so we had a lot of options. Almost too many options!

We had to be in San Diego for the Travel and Adventure Show on March 4 and 5. When I first tossed the idea of driving instead of flying to my husband he asked how long I thought we'd need - "three weeks? A month?"

Gleeful that he was even open to the idea, I figured we'd need a month. One week in San Diego, a week and a half getting there and another week and a half to get back seemed just about right.

Our calculations took into consideration that we didn't want to drive more than four solid hours per day, if we could avoid it. If most of the time was spent driving we wouldn't be able to pull over at every historical marker and lookout point, and that was a priority, man.

We also wanted to have time to explore the towns we visited, get in some good hiking, and have some time to relax.

This was experience speaking. When we drove Route 66 in 2011 we had sixteen days to drive from Chicago to Santa Monica and back. There were some long driving days in there, but they became even longer when we ended up in Amarillo for four days - a quarter of the trip - after someone backed into our car.

That meant the rest of the time we were racing to catch up and get back by our deadline. It takes some fun out of a road trip when you're spending most of the day, for days in a row, on the road itself.

So, four hours of driving per day over a period of ten days each direction. That still left a lot of options. We began to narrow them down by thinking about what we really wanted to see and how we wanted to get there.

Step 2: Know Your Interests

Things that get me jazzed about traveling:

  • history
  • architecture
  • hiking
  • beauty
  • cool people
  • stunning views
  • diversity
  • learning
  • seeing mother nature in all her glory
  • seeing humankind in all its glory
  • discovering new (insert noun here)

The list could probably go on, but those are my main considerations. They're pretty broad, so this is how that list translated into actual destinations.

We knew we wanted to avoid interstates more often than not. When you get off the highway and onto the two lane roads you see more of what this country offers. From the highway you only get a glimpse of gas stations, fast food joints, and the occasional fireworks stand.

That meant that our four hours of driving would cover less distance because we wouldn't be doing 70+ MPH without stops.

By taking two lane roads we could visit off-the-beaten-path locations and we saw more roadside attractions. We visited Cadillac Ranch again, but we also saw new kitschy, cool and unique things we wouldn't have seen from the highway.

By visiting small towns we met a brewer who turned his hobby into a business and visited a refuge that rescues wild cats.

We also love being outdoors and love camping. (As in, I get slightly obsessed with it.) That means we visited as many parks as we could and took advantage of the easy one-minute setup with our Coleman instant tent. I love that tent almost as much as I love my iron skillets. Almost.

We knew we were going to be in some Dark Sky areas, so sleeping under the stars was a must. This was a need, not a want.

We included some day visits for hiking. Places like Wichita Mountains Wildlife Refuge in Oklahoma, El Morro National Monument in New Mexico, and Zion National Park in Utah. I'd wanted to visit Mesa Verde National Park for as long as I can remember, and on this trip, I did.

In addition to camping, we stayed at a couple of bed and breakfasts and some places that were unique to the destination we were visiting, so we got to meet locals who were passionate about their home and other travelers who wanted a more involved experience than a chain hotel often provides. 

Step 3: Check the Weather

This is where my husband was the voice of reason. I was all like "ooh - let's take the back roads all the way through Illinois and Missouri and then let's camp everywhere" and he was like "Theresa - we're leaving in February."

Sigh.

(This is why it's good to travel with someone with different strengths. Him = practical. Me = not so much.)

While I would have loved to camp at Mesa Verde, the campground didn't even open until mid-April. I wanted to explore spots of Route 66 in Illinois that we missed the first time around*, but there was the possibility of snow and lots of uncleared roads. Our return trip through the Rockies needed to be flexible because it was in early March and who knows what's going to happen through those high-altitude passes. 

*We missed a lot because we didn't pick up the "EZ66 Guide for Travelers" by Jerry McClanahan until we were in Missouri. If you plan on driving Route 66, GET THIS BOOK. {affiliate link}

However, the timing also meant that camping at Joshua Tree was perfect, and our visit to Yuma, Arizona, was a lot more comfortable than it would have been in August. No matter when you take a road trip, weather should be part of the planning process.

Step 4: Set Goals

Setting goals for a road trip might seem like an odd way to plan, but if you know ahead of time what you're hoping to gain from the experience, your planning will be much easier. A lot of those goals are based on your interests, but some of them are more esoteric, and all of them are your own.

An obvious goal of this trip for me was research for The Local Tourist and "Two Lane Gems, Vol. 1," but I also had some personal hopes.

One of them was spending quality time with my husband. While we work from home and spend more time together than any couple I know, we spend most of that time working. This trip gave us an opportunity to connect on a deeper level.

Another was that I hoped to fully own my dreams and clearly see the path to achieving them. I've made some big changes in the past year, and writing a book is the biggest. This road trip was me stepping away from the day-to-day and literally making my dream a reality.

Did it work? Yes! My husband and I did grow closer, and the personal growth and changes I've experienced have been remarkable.

When you're planning a road trip, figure out what you hope to gain from the experience and it will help you tailor the places that make it onto your itinerary.


If you're thinking about planning a road trip, these steps should help you choose your destinations. Do you have any tips for planning where to go? If so, please leave a comment!