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What is the single hardest part of planning a road trip?
Choosing your road trip destinations.
This is a big deal. If you choose the wrong road trip destinations then your entire vacation will be ruined forever and ever and you’ll never want to take another road trip.
If you don’t do this right, if you don’t choose your road trip destinations wisely, you’ll feel like a complete failure.
This is a BIG DEAL.
I’ve been on a few road trips. In 2011, my boyfriend and I took sixteen days and drove Route 66. It made such an impact that we got married on June 6 – 6/6.
Then, in 2017, I had a booth at the San Diego Travel & Adventure Show. I asked my then-husband how he would feel about driving this time instead of flying. I knew this would be a bit of a commitment since we live in the Chicago suburbs. His response?
“Sure – how long do you think we’ll need? Three weeks? A month?”
We drove, taking 31 days. A week of that time was spent in Southern California, and yet we still managed to cover 6,479.5 miles. It was an epic trip, and when we got back, I made 10-year-old me very happy by writing my first book.
In 2018, we took 35 days and drove 6,832.9 miles to the Oregon coast and back, and my 2nd book, Two Lane Gems, Vol. 2, came out in December of the same year.
We’ve also taken shorter trips. Up north to Marquette, Michigan. A few hops to North Central Iowa. Annual visits to Asheville, North Carolina to see my parents. In 2020, I literally drove around Illinois, sleeping in the back of an SUV, to research the state for Midwest Road Trip Adventures.
Like I said: I’m addicted to road trips.
None of those trips 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.
Over the course of all of those miles I’ve learned a thing or two about how to choose road trip destinations, so I’ve got a few tips to share. I hope they help you when you’re planning your next adventure!
How to Choose Road Trip Destinations
1. How much time do you have?
The first thing to figure out when you’re planning your road trip is how long you’ve got. A weekend? A week? A whole month?
A month-long trip is a whole different beast than a weekend tour. It’s the biggest determining factor in how far you can go.
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 we’re going for a week, we’re willing to drive further to get there since we’ll be in one place for a few days. And, if we’re going for a month, our options are as wide open as the wide-open road.
2. How long do you want to spend driving?
Do you prefer to drive long stretches so you can spend more time at a destination, or do you like to take shorter hops and visit more places?
We try to pack as much in as we can on our epic road trips, so that means we tend to stay at each place for one night. Because of that, we try to limit our driving time to four hours per day. It doesn’t always work out that way, but that’s our goal.
Of course, that means that it actually takes us anywhere from six to eight hours to get from one place to another. However, the beauty of a road trip is that you have the freedom to stop and take a look around.
Historical marker? Pull over! A local tells you about an amazing spot that’s only half an hour out of the way? You better believe we’re going!
So, your first step is to figure out how many days you’ve got. Then decide how many hours you want to drive each day, and then add half again as much for random stops.
Trust me on this.
3. What are your interests?
What do you want to see on your road trip? While you’re planning, think about what you really want to experience and make a list of things that get you jazzed about traveling. Here are a few of mine:
- cool people
- stunning views
- 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 major considerations. As I’m looking at potential destinations, I’ll see if the criteria match up with what each place offers.
4. Do you prefer interstates or two-lanes?
Do you want to get there fast or take the scenic route? We generally try to avoid interstates (hence, Two Lane Gems).
When you get off the highway and onto the two-lane roads you see more of what this country offers.
It’s easier to visit off-the-beaten-path locations and find roadside attractions. It enables us to see kitschy, cool and unique things that aren’t visible from the highway, like a Volkswagen Beetle on stilts in a corn field.
However, it does take longer (especially with all those historical markers), so that means our four hours of driving cover less distance because we won’t be doing 70+ MPH without stops.
Most of the time, the slower route works for us. Sometimes, though, we just want to get to our destination. Whatever your road trip style, the type of road you take helps dictate where you’ll go.
5. What kind of accommodations do you like?
My husband and I are campers. C-A-M-P-E-R-S. As in I’m slightly obsessed, and start jonesing if I haven’t pitched a tent or cooked on an iron skillet over a fire in a while, and we’re on the hunt for the best Midwest camping spots.
Some of my friends are fellow camping enthusiasts. For others, a hotel without room service is their idea of roughing it.
I get it. While we love camping, we also enjoy luxurious accommodations, historic hotels, roadside motels, and cozy bed and breakfasts. Each type provides a different experience.
Since not every option is available everywhere you go, knowing your preference will help narrow down your road trip destinations.
TLTip: if you’re a tent camper also, or want to be, I recommend the Coleman instant tent. Set-up and break-down take ~ 5 minutes for one person, giving you more time for ‘smores and exploring the wilderness around you.
6. What’s the weather like?
What will the weather be like when you plan to visit? This is a big, giant, important consideration when you’re choosing your road trip destinations. You’re probably not going to head to the desert in August, or the mountains in December.
When we drove to San Diego and back, we left the Chicago suburb of Elgin Illinois in mid-February and returned mid-March. That impacted what we could do and where we could go.
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.”
(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 in 2011*, but February in Illinois is iffy, weather-wise.
Likewise, our 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.
The flip side is that the timing also meant camping at Joshua Tree was perfect, and our visit to Yuma, Arizona, was a lot more comfortable than it would have been in August.
*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.
No matter when you take a road trip, weather should be part of the planning process.
7. What are your goals for your road trip?
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, finding your ideal road trip destinations will be much easier.
You’ve already made decisions based on goals. For example, one goal may be to not get stuck on the side of a mountain in a snowstorm, or to not die of thirst in the desert. Maybe your goal is to visit all the National Parks, or to drive all the Scenic Byways.
One of my goals when we visited Yellowstone National Park was to see Grand Prismatic Springs (pictured). This is one of the most popular “hot” spots in the park.
To achieve that goal, and to stay within our budget, we knew we’d need to camp in Yellowstone. If we hadn’t, we never could have gotten to the springs early enough. (Tour busses. So. Many. Tour busses.)
We also had a bucket list experience camping in the middle of the bison after driving through Badlands National Park.
Related: tips for visiting National Parks
Some goals may be more esoteric.
For me, an obvious goal of our 2017 trek across the southwestern U.S. 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’d made some big changes before that trip, and deciding to write a book was the biggest.
That epic road trip was a decision to step away from the day-to-day and literally make my dream a reality.
Did it work? Yes! My husband and I did grow closer, and the personal growth and changes I experienced were remarkable.
And as you now know, I wrote that book.
When you’re trying to choose road trip destinations, figure out what you hope to gain from the experience and it will help you tailor the places that make it onto your itinerary.
Tools to help you choose road trip destinations
Now that you’ve got an idea of how long your road trip will be, what kinds of things you’d like to see, the general direction based on weather, what type of accommodations are ideal, and what you hope to get out of it, how do you actually find those road trip destinations?
There are a few tools I use that have served me pretty well over the years. Hopefully, they’ll help you, too.
8. Attend a Travel Show
Travel Shows are a great way to find new road trip destinations. While many people attend hoping to connect with someplace exotic (a.k.a. a place requiring several hours in a plane), travel shows are a wonderful way to find someplace a little closer to home.
I’ve exhibited at the Chicago Travel & Adventure Show since 2014, and the San Diego Travel & Adventure Show since 2015 (and have spoken about choosing road trip destinations and road trips from Chicago).
Every year I’ve found new places to visit that are within a few hours of those cities, making them easy places to visit.
Places I’ve traveled as a direct result of connecting with destinations at these shows include Cottonwood, Arizona; Medora, North Dakota; Bishop, California, and the nearby Museum of Western Film History and the Alabama Hills.
The people working the booths at travel shows are, generally speaking, from the destination they’re representing. They know more than anyone about their home and it’s their job to fill you in on why it would be a good place to visit.
They’re a great resource, and can open up new places you might not have considered.
9. Use Roadtrippers.com
Excuse me for a moment while I wax rhapsodic about this immensely useful tool for finding road trip destinations. Roadtrippers.com allows you to plug points into a map, but it’s so much more than that.
Once you’ve added your starting point and your destination, you can then choose to either take the highways or avoid them. This visually opens up possibilities you might not have considered.
For example, after meeting Cottonwood, Arizona, at the Chicago Travel & Adventure Show, we knew we were going to visit that town near Sedona.
I also knew I wanted to visit the lowest bar in the Western Hemisphere, located in Bombay Beach, California. By plugging in both destinations and then telling Roadtrippers I wanted to avoid highways, it routed us through Yuma, where we had some of our favorite experiences on the trip.
Besides plotting the route itself, there’s a ton of user-generated content offering recommendations for attractions, restaurants, places to stay, and great photo ops.
There’s an app, too. The website is better for planning. Once we’re on the road, I use the app as an itinerary.
Check out my complete guide to Roadtrippers and you’ll see why I love it so (and get a discount for Roadtrippers Plus)
10. Get a AAA Membership
One of my road trip rules is to always visit AAA before heading out.
One word: Maps.
Sure, the roadside assistance and travel discounts come in handy, but it’s the maps that keep me renewing my membership each year.
Even though GPS is great, sometimes, like in the canyons of Utah or the middle of the Mojave desert, it doesn’t work. That’s why we always, always, have paper maps of the destinations we’re visiting.
Their app is also a good resource, if you do have a connection, for finding attractions and restaurants, but the next (and final) tool is even better.
Related: How to save money on a road trip
11. Ask the locals
My favorite part of travel is the people. On our Oregon coast road trip and back, not a whole lot was planned. We relied on the kindness of locals, like the volunteer above at Heceta Head Lighthouse, to point us in the right direction, and we were richly rewarded. People who live where you’re going are always your greatest resource.
While you could drive by the seat of your pants, like we did, there’s an easier way:
These gems are my travel planning secret weapon.
When you’re planning your trip, make sure you reach out to these founts of regional knowledge. In the “biz” we know them as CVBs – Convention and Visitors Bureaus – and DMOs – Destination Management Organizations. These are the Mother Lode of local info.
It’s hard to say what I love best about Visitors Bureaus:
- They know their markets.
- They bring money into their communities.
- They’re passionate.
- They’re free.
Our visit to Yuma, Arizona, is a perfect example of why I consider these resources treasures. We talked with a representative of Yuma’s Visitors Bureau. When we told her our route, she told us about the Museum of History in Granite and the Center of the World, and about Salvation Mountain.
Those two stops provided some of our favorite memories on our trip, and we never would have known about them without a local’s input.
Once you’re at your destination, ask the people you meet – the gas station attendant, the cashier at the grocery store, the concierge at your hotel, the host of your B&B – where do they go to lunch?
Where do they take family when they come to visit? I’ve never been steered in the wrong direction, and have found some real gems just by asking the locals.
If you’re thinking about planning a road trip, these steps should help you choose your destinations. Do you have any tips for choosing road trip destinations? If so, please leave a comment!
And don’t miss my 50 Tips for Planning an AMAZING Road Trip, complete with free e-book.
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