The Art of the 21st Century Road Trip (Hint: Screw Road Trip Planner Apps)

By Ethan Maurice | February 19th, 2019

In the United States, road trips are almost a rite of passage — our ultimate symbol of escape, freedom, and adventure. From the written works of Kerouac and Steinbeck to a laundry list of films that take place on the open road (from Little Miss Sunshine to Into the Wild to Rain Man), we’ve culturally come to recognize the road trip as the antidote to too much city, sameness, and domestic life.

After crisscrossing the American west more than half a dozen times by car, driving the entire west coast, and spending more than five months of 2018 living out of a Honda Element converted into a home on wheels, a sharing of my take on the art of the 21st century road trip has felt long overdue.

However, it wasn't until I conducted a bit of “road trip” keyword research, that I found the fire to pen this piece.


I discovered that the most searched keyword associated with “road trip” is “planner.”

road trip planner

Searching “road trip planner” returned a bunch of websites and apps built to plan your entire trip before ever leaving home. The most popular planning app, Roadtrippers, looked pretty sweet. Their website and app, beautiful and user-friendly. Many of the best spots in my neck of the woods were marked as points of interest as well.

That said, this article was not written to recommend road trip planners, but to save you from them. Because planning your entire trip before leaving your driveway will remove the presence, serendipity, and sense of adventure from your time on the road.

Road trip planning technology offers an exchange: swashbuckling adventure revealing itself on the knife's edge of the present moment swapped for a GPS-guided visitation of what’s best.

It’s my great hope that this article lands in the top of those 74,000 monthly searches for “road trip planner,” saving serendipity and the spirit of the open road for the those looking to plan their entire journey beforehand.

With the intention of keeping the spirit of the open road intact, here are fifteen tips for your 21st century road trip:

1. Keep your options open (don’t map with a road trip planning app).

The most important point of this whole article: keep your trip flexible enough to adapt in the present. This is vital because it makes the present exciting, an experience carved out of opportunity as it arises.

An example: the Yesman and I were on a week-long road trip throughout the Southwest, camping on the shoreline of Lake Powell. Under the Milky Way in the faint light of our campfire, our neighbor mentioned she heard something about a hot air balloon festival the following morning in a nearby town. With a schedule to stick to, we would have never had the spontaneous experience of inflating, chasing, and floating around in hot air balloons in the desert sunrise.

Rather than plan your whole trip beforehand, build a rough idea of where you’re going and your options. I often hand-draw a map full of potentialities and combined with the resources mentioned further along in this article, make decisions as they present themselves.

A map of options from my west coast road trip.

A map of options from my west coast road trip.

Other times, like on a three-week road trip with a bunch of French people in New Zealand, I've intentionally blinded myself to all options to double-down on what the open road is all about: serendipity and adventure.

2. Pack the essentials and not much else.

The room to stretch out in my Durango was a wonderful thing.

The room to stretch out in my Durango was a wonderful thing.

Don't bring everything you think you might need. On the road, you're more or less living out of your car — save some space to live in. Don't bring have half your closet, better to stop at a laundry mat along the way. A cooler is cool, but there will be plenty of places to pick up food.

Rather than a comprehensive list of everything you could possibly want, here are some especially worthwhile items to bring on the road:

A note for those bringing any illegal substances: Be wary if you’re driving within seventy-five miles of the US-Mexico Border. There are a bunch of interior border patrol checkpoints with dogs that are very good at smelling them.

3. Finding places to stay:

With a tent, or the ability to sleep in your vehicle, will be your best friend. Stay with locals for free through Couchsurfing. Use Airbnb for funky spaces with a bit more privacy. If booking a hotel room, search a major hotel search engine (they'll paradoxically give you a better rate than if you call or walk in). Last resort, you're allowed to sleep in your vehicle in most Walmart parking lots (but without window shades, parking lot lights often result in restless sleep).

4. Finding things to do:

The Outbound Collective is the best kept secret for finding awesome things outside. Yelp will point you towards the best local restaurants. Google “top 10 things to do in ______” will lead you to some of the best stuff around as well. I also used this website to find parks with free workout equipment while living out of my Element.

Sharing a surreal sunset in Arches National Park.

Sharing a surreal sunset in Arches National Park.

All that said, don’t totally rely on the internet to dictate your adventure. Ask other humans for advice whenever possible. Locals still have the best answers, and more importantly, asking others opens up the opportunity to do things with other people.

Lastly, if you're ever within reasonable driving distance, check out Meow Wolf.

5. Music is quintessential to the road trip experience.

Playlists rock, but don’t you think shuffle gets old? I prefer albums. Or just bring one CD and play it over and over again like my buddy Mellit and I did for three weeks straight (UB40's I Got You Babe will forever be our theme song). Speaking of theme songs, pick one and play it way too often – you'll always associate it with your trip and that is a wonderful thing. Turn off the music sometimes too. The constant closeness with your compadres allows for many an opportunity for serious conversation. Silence is can be golden as well.

6. Coffee shops and fast food joints are cheap places to chill.

I'd be embarrassed to tell you how much time I spent in Starbucks and McDonald's during the five months I lived in my Honda Element. These corporate chains are everywhere, have long hours, and are heavily invested in inviting interiors with solid wifi. Countless are the times I’ve bought two $1 Hot 'n Spicy McChickens to spend three hours at work in a McDonald's or a “grande dark roast in a for here mug” at Starbucks for $2.39 to do the same.

7. Some epic things to do along the way:

The secret to enjoying the Grand Canyon is to go into the Grand Canyon.

The secret to enjoying the Grand Canyon is to go into the Grand Canyon.

Spend lots of time outside, away from your car: climb mountains, explore slot canyons, go cliff jumping, soak it up in hot springs etc. Again, The Outbound Collective is great for this. When visiting national or state parks, ask the gate attendant how to experience the greatest degree of wonder.

Drink with strangers at a bar in the city, or the people in the campsite next to you. Spend a night far from city lights to see the stars how you were meant to see them. Be overly curious at muesums. Get thrifty at Goodwills in cities, especially in wealthy areas.

8. Have fun dude!

The funnest French people I know.

The funnest French people I know.

Good times are a top priority here. From time to time, we all forget to make the best of what comes along and act a tad like cynical sticks in the mud. It’s cool, but listen: you're sowing the seeds of your own sadness with resistance to what happens along the way. If your car breaks down and you're stuck for three days in Nowheresville because Bob the mechanic has to mail order a part to fix your radiator, it's up to you to make the most of that weird, boring, memorable experience.

If you're not embracing the moment, you're creating resistance to what is and totally sabotaging yourself dude.

9. Play the best road trip games:

  • The High-Five Game. Collect as many high-fives as possible from strangers in a set amount of time. This is a great game to play at rest stops, downtown, or in other congested areas. Usually, you're limited to one high-five per person, but convincing a stranger to give you one hundred high-fives is pretty awesome and should be considered a viable option as well.

  • The Anal RV Game. It’s not what you think! RV's just have the best names. Add the word “anal” before or after to make them even better.

  • One Hundred Yard Dash. Sometimes after hours of driving the best thing you can do is pull over and hold a good ole' fashioned foot race down the side of the highway with your friends. It's good for the soul, for your sense of freedom, and gets the blood flowing in your legs. If you've been sitting for hours, there's a decent chance someone will tweak a muscle — keep this in mind, especially in your first couple steps off the line.

  • High Stakes Musical Chairs. Many know this as a “chinese fire drill,” but that's kind of racist, so I just made up another term right now. The driver stops at a red light, puts the vehicle in park, and yells “high stakes musical chairs!!!” Everyone must exit the vehicle and find a new seat before the light turns green. If the light does turn green and someone takes longer to get back in than everyone else, the new driver is free to leave them at the intersection. It's in good taste to make them walk less than a mile to get back to the car, but teasing them by lightly stepping on the gas as they're about to climb back in a couple times is highly encouraged.

  • Padiddle. Someone spots a vehicle with one headlight out: they yell “Padiddle!” and slap the roof of the car. Everyone else must slap the roof of the car. The last person to do so must remove an article of clothing. Clothing cannot be reapplied until the next destination is reached. For a greater frequency of clothing loss opportunities other happenings can be added such as yellow lights, certain types of cars, and road signs.

10. Don't use your phone too much.

Your phone is the chief distraction from everything unfolding in front of you. It tethers you to home, to news, to social media – to everything going on somewhere else. Part of the purpose of the road trip is to step away from your life back home and view it from an outside-in perspective. Your phone can totally sabotage this perspective switch.

Use your phone for good: for navigation, music, finding what's best to do today, letting your people know you're alive etc. Not for evil: allowing news and social media to pollute your experience, a means of alleviating boredom, or withdrawing from awkward situations etc.

11. Take photos after the experience.

Perhaps the slipperiest, most dangerous combination of technology is a camera paired with social media, offering a trade our socially-wired brains are too tempted to make: the firsthand experience of life for future social approval. Which is why places people want to see most have paradoxically become places where people see least. Instead of revel in wonder, most opt to siphon the experience through the straw of a screen as they set their mind to extracting a profile picture from the experience.

A complex problem we could spend much thought examining, there's a simple solution: experience it first, capture it after.

12. Navigate without turn-by-turn directions.

Map Apps are not designed to get us there the best way, they’re designed to get us there the fastest way. Leaving interstates for “blue highways,” the backroads of America, offers a more varied, authentic experience away from the corporate-chain-lined, high-speed grooves of interstate-sameness paved across our country. As CBS correspondent Charles Kuralt once so perfectly put it:

“Thanks to the Interstate Highway System, it is now possible to travel across the country from coast to coast without seeing anything.”

Instead, seek the scenic route. This is most easily done with a set of printed maps, but you can use your map app without asking it for directions as well. At minimum, consciously choose between the couple routes your GPS offers. A big part of a road trip is deciding where you’re going to go. Don't totally entrust your adventure to algorithms — make some decisions, and mistakes, yourself.

13. Go when the going is good.

Spending a couple early November days in Big Bend National Park.

Spending a couple early November days in Big Bend National Park.

Generally speaking, winter is not the ideal time for a road trip. In most places around the United States, summer rocks. If you're spending a lot of time in the desert, spring or fall might be better.

Also worth noting: there are certain times in the year when rental cars migrate to different areas around the country. If you don't want to put the mileage on your own vehicle, here's how (and when) to get one for next to nothing.

14. Go where the going is good.

Here's a great list of route inspiration. But following the serendipitous theme threaded throughout this article, remember, there’s no need to follow a set route. String some National Parks together, cruise the Pacific Coast Highway, Highway 50 (America's loneliest highway), or Highway 89 (my favorite stretch of pavement between Flagstaff, Arizona and my thrice summertime gig running an old lodge next to Yellowstone).

Having covered much of the United States by car, bicycle, and boat over the last five years, I've come to the conclusion that “west is best” with wider spaces, bigger mountains, and weirder, wilder landscapes. If mountains are your thing, weave along the Rockies or throughout the west coast ranges. The red rocks of southern Utah are otherworldly. There's something about the Arizona/California desert as well…

15. A few parting words about the art of the journey.

summer days on the road

If there really is an art to the road trip, it lies in the ability to be where you are. All too often, we’re two years and a thousand miles in the rear view mirror, or an hour and seventy-five miles up the road.

To give yourself to the passing headlights, high noon at a deserted rest stop, or whatever else you are experiencing in this moment is the truest art of the road trip. This moment, not merely a means to another, but your constant kaleidoscoping destination.

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