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.”

3. Start slow.

We began our trip in Orange County, at a property called The Ranch at Laguna Beach. The hotel is an absolute anomaly in a busy beach town: It’s an oasis, where life feels free and easy. Also they make this bacon cinnamon roll that pretty much replicates an optimal drug experience. I mean, not like weed or a stiff drink, but certified, tested MDMA — the sort that makes you feel like you are in all the world and all the world is in you.

Is that too dramatic and emphatic of a reaction to a breakfast pastry? Nope. This thing is flakier than late-90s Ashton Kutcher.

Anyway, we started in this shady canyon — feeling far away from it all and removed and… tranquil. For the record this was the first road trip I’ve ever kicked off with any sense of tranquility. Before this, I had a unbeaten record of road trips starting out frenetic and disjointed. From here on out, consider me a chill-start convert. After some pool lounging and a second cinnamon roll around 12, we hit the road. Not a worry in the world.

4. Never drive for more than four hours at a time.

Don’t get it twisted: There’s a huge difference between “road trip” and “trying to cross the country in a very short time, but let’s stop for a burger or something.” The latter is not a road trip, it’s some other beast entirely. If you’re going on a true road trip, you’ll need to see more than just asphalt. Realistically, every day of the trip should have a “thing” — some iconic, memory-worthy activity — whether that’s an unforgettable meal, a hotel that speaks to your aesthetic, or an experience that you couldn’t have had back home.

Point being: It’s not all about the drive. Try to max out at six hours per day of car time, with no more than four hours at any one stretch.

For Nikta and my first day, four hours put us in Santa Barbara, at the Klimpton Goodland Hotel. The Goodland is one of those hotels that focuses on being more than just a place to sleep — they offer an experience. The rooms have record players and there’s a vinyl shop in the lobby; the bar serves a bespoke beer, created in collaboration with a local brewery; and the design of the property feels like it’s borrowed the beach bungalow chic of Altman’s The Long Goodbye. The macrame game at the Goodland is on point and there’s a dedicated backgammon table in the lobby. It’s just that sort of spot.

5. Your “Shortest Path” can’t be your route.

From my current house in Orange County, California to my old neighborhood in Portland, Oregon — the eventual destination of this trip — you can take the I-5 for all but two miles. But road trips are meant for the “blue highways” (the color designated for scenic routes on old Rand McNally atlases). You have to zig and zag a little. You have to follow your nose. You have to be willing to head a new direction, even when the timing doesn’t quite work and you’re running late to get to your next stop.

Which explains how we ended up spending an afternoon surfing and lounging on the beach in Morro Bay while the chances of making our dinner reservations in Napa a few hours later, plummeted to zero. There are few things on this earth more satisfying than canceling plans in order to surf, read, and flirt on the beach with a pretty girl. It’s my philosophy that these opportunities deserve to be seized and celebrated.

6. Listen to good music.


This is a no brainer. Good music is good. People who don’t appreciate that are sociopaths who are probably standing behind you right now with massive knives, glinting in the moonlight.

That said: No one likes the same music. I consider my personal musical tastes to be the best on earth and everyone else is a helpless prole. But that’s how it goes with matters of taste. Besides that, the playlist below is littered with songs that meant something to me when I was a 19 year old college dropout, hitchhiking around the country with nothing but a Sony Walkman. Technically, my tastes were probably at their least refined (though I’ll still argue that Eve 6 was deeply underappreciated).

A road trip playlist is a sacred thing — make your own. But if you want to sample mine, here you go:

7. Go someplace that everyone is hyped about…

From Morro Bay, we headed north to Napa Valley. Everyone knows Napa. Everyone loves Napa. It’s a worldwide haven for food and wine. And yet… I’d never been. Not even for a tasting. Not even when I was working on horse ranches in nearby Santa Rosa.

And here’s the thing with places that everyone has been to and adores: They’re usually pretty awesome. So it was with Napa for me. What was there not to love? We stayed at a hotel where they give massages in a cave! And you can play bocce while drinking wine! And the pool is 21+ so that you can drink wine there, too! And literally everyone is friendly drunk but not staggering drunk every second of the day! It’s awesome.

That night, we stayed at The Meritage Resort And Spa — the sort of place that every road trip needs at some point: A hotel where you can slow down and pamper yourself by drinking a vintner’s blend chardonnay by the pool. The sort of place where getting buzzed gradually is a skill to be mastered and the only time constraints are scheduled wine tastings and dinner reservations. Those can be pushed back. Trust me, there is no host or hostess anywhere who is as used to hearing “We’re running a little late” as those in Napa Valley. As a person who gets deep satisfaction from changing plans, I loved it there.

8. And someplace that isn’t on anyone’s radar.

As a traveler, I’m intrigued by the idea of the “hidden place.” Both because the very notion of secret spots is a myth, and because I’ve discovered a fair number of “untouched gems” that were absolutely extraordinary.

When I say that secret spots are a myth, what I mean is: People have been everywhere. Unless you’re in the ice deserts of Antarctica, you’re probably not seeing virgin vistas as you parade around this mortal coil. The key is to find places that feel new and underutilized, to make them your own, and to explore with a sense of awe. Imagine them as a secret whispered just to you, whether that’s true or not.

NAME REDACTED waterfall in Oregon is one of these sacred places. I can’t believe more people aren’t going to NAME REDACTED — though I get it. It’s secluded and far from everything and absolutely drowning in poison oak. As a result, you can pretty much have it to yourself.

Nikta and I found NAME REDACTED through my cousins. They hopped in the Volvo after meeting us at the Prineville Reservoir in Eastern Oregon and led us to this little slice of “no signal” paradise. We swam down gurgling streams in order to avoid NAME REDACTED’s poison oak infestation, and eventually washed up on the banks of a hidden beach, surrounded by swaying oaks. It was perfect and, for one day, it was just ours. That’s hard to beat.

9. Have a road hobby.

Nikta and I play “Backpacker’s Uno” obsessively. We also skateboard at rest stops and listen to the podcast “My Favorite Murderer” (what can I say, it’s a match made in heaven). For the whole trip, I was obsessing over taking Polaroids — even though they cost $1 per picture and about half of ours never developed. Money isn’t the point, the point is that the roadside card games, midnight polaroids, and hours spent cringing through gruesome podcasts are what you end up remembering from a trip. So make sure you have those things in place.

10. Get to a proper city.

We ended our trip in Portland in August — just the sort of place you want to be in August. In fact, summer in Portland deserves to have odes written about it. Nine months of rain leaves the city feeling… moist. So when the heat hits, it’s not a dry heat, or event particularly unpleasant. Water is evaporating from the watershed and your skin still feels cool. It’s never muggy, plants are blooming and if you ride your bike on a really hot night at about one am, you will find people out in the streets and you will think “The world is full of beauty and wants me to be happy.”

It’s a magical place, in a magical season.

We stayed at the Marriott Waterfront because Portland’s selection of paths, coffee shops, restaurants, and bars along the Willamette river is second to none in the nation. At night, we looked out over the whole city and got to enjoy the hotel’s amenities after a long few days in the car. In the day we biked, swam in the river, ate and hung out at Powell’s Books.

Portland’s waterfront is where you can find some of the best clubs in the region and a 3am donut, fresh out of the fryer. It’s perfect for the end of a long road journey.

11. Finish. Freaking. Strong.

This is crucial. You have to go out with a bang. Our Great American Road Trip ended at Pickathon — a convergence of hippies and hipsters and hip-hop heads held in the Oregon backwoods. Real talk: this fest might just be the chillest, most eco, best-vibe jam weekend on the planet. In the span of three hours, you can listen to rappers playing inside a barn, soul funk on a secret forest stage, and granola-fed corduroy rock under the blinking stars.

I can’t imagine a year where I won’t be at Pickathon from here on… until always. I’m just a sucker for drinking a cocktail and eating a fried chicken sandwich while some dude with a beard sings about gristle and grain. (Sidenote, if all the hipsters who wrote ballads about barley and wheat really farmed the stuff, we could feed the world.) Point being: It was the perfect conclusion to our trip.

* * *

So there it is. Notes from a summer on the road. And of course, my trip can never be your trip, but you’d never want it to. With luck, it might spark something and motivate you to grab your keys and go. And then, when the asphalt is unfurling under your tires, and the planet seems to be drowning in sepia tones, you’ll be glad you went. And I’ll look for you, out there, on the road, leaning forward toward the next crazy venture beneath the skies.