The Definitive Rules For The Best Road Trip Of Your Life

“What is that feeling when you’re driving away from people and they recede on the plain till you see their specks dispersing? – it’s the too-huge world vaulting us, and it’s good-bye. But we lean forward to the next crazy venture beneath the skies.”

― Jack Kerouac, On the Road

For me, the road has always been “the thing.” It’s where my best sides reveal themselves; where I feel the funniest, the smartest, and the most alive. The road is where I become one of the Mad Ones, to co-opt another Kerouac quote. Where I “never yawn or say a commonplace thing, but burn, burn, burn like fabulous yellow roman candles exploding like spiders across the stars.”

This summer, after a winter that was more sedentary than my spirit is built to handle, I finally got on the road again. In July and August, I drove up the California 1, then skipped over to the I-5. After crossing state lines, I veered deep into Eastern Oregon’s high desert, before tracing a winding path to Portland. Two weeks in, I realized that I have a pretty solid playbook for road tripping. I have songs for the slow stretches and card games for the rest stops. I have more thoughts on the perfect roadside milkshake than I do on the soulessness of the stock market (which is to say: a lot).

Point being: I take this shit seriously. Because good travel is, at its best, an artform. Like any art, you can’t steal from a fellow traveler and recreate their trip with any passable level of verisimilitude. But you can pick up a few new tricks and rules of the road.

1. Choose a ‘smart’ car.

I am the owner of the worst road trip car on earth. It beeps incessantly. When I back up, it beeps. When I have my seatbelt off — even for a Goddamn millisecond — it beeps. When there’s a bag on the front passenger seat that might weigh as much as a human, if that human had bird bones and no muscle, fat, or sinew, it beeps. Yes, it gets nice gas mileage, but I would literally tunnel to the center of the earth, sop up a barrel of crude oil inside the fossilized skull of a t-rex and refine it in my backyard before driving my current car on a road trip of any length. It’s just too annoying to drive for long distances.

Instead, I went with a rental. It was the perfect road trip car — intuitive and logical where my car is shrill. When you take your seat belt off, it dings three times. Not beeping, mind you. This was more like someone tapping a glass bowl in a monastery.

“You want to be unnecessarily reckless?” it asks. “That’s on you, bub. Hope you Americans have good health care.”

But the car also won’t let you run cruise control or pilot assist without your seatbelt on. There are literally whole books on this basic theory when applied to childhood development: My rental shows you what you’re missing through your refusal to follow rules, rather than screeching at you. It works amazingly.

The right car for your trip might be a modified Sprinter van, or a convertible, or a station wagon with backward facing seats in the trunk. The point is: Make it an active choice. And don’t pick something that beeps a lot.

2. Choose a great co-pilot.

Here’s an excellent rule to live by. If you ever meet someone, anyone, who says, “I’m an easy travel companion!” Do not travel with them. They are not easy.

  • Good lovers do not tell you they are good lovers.
  • Talented writers do not tell you they are talented writers.
  • Easy travelers do not tell you they are easy travelers.

Please trust me on this. My most agonizing trips have always been with people who started the whole let’s-go-on-a-trip convo with “Me? I’m easy!”

For this adventure I picked my girlfriend, now wife, Nikta. Granted, we got married the day before we left, so not going together probably wouldn’t have gone over too well. But she likes True Crime podcasts, roadside BBQ, and singing to Boyz II Men, so… what else do you need?*

*Along the way, we eventually picked up a motley collection of cousins and friends — intrepid types who happily braved Poison Oak to reach an idyllic waterfall, moshed in the front row at a music festival, and sipped blackberry milkshakes while battling at Uno. These are the sorts of humans you “grapple to thy soul with hoops of steel.”