How to plan a road trip has nothing to do with where you’re going. In early spring of 2014, I had no idea where to go, but I had to leave LA fast. I couldn’t take it anymore; I needed outta California. I couldn’t relapse, no. That’s not an option. No drink for me. It was like the first of three breakups with the girl I was with… one of those relationships. I bet she fucked like three hipsters at Coachella. Probably did. But now I had to forget all about her ASAP and take a road trip.

There was this hip hop publicist. I met her on Twitter. I found her in a hashtag… We had virtually no idea who each other was. She lived in Minneapolis. I sent her a DM: “Where should I go? I need to leave. Taking a road trip. And wherever you tell me to go, I will go.” I was hoping she’d say Minneapolis so I could fuck her (and have some kinda direction of where the hell I’d actually be driving, cause I would be driving.) She wrote:

“Minneapolis, duh!”

Phew. “On my way.” 

Now I had an endpoint. Let the journey begin.

I hate driving with no destination; now I have one. On to Minneapolis I go. It’s only a couple thousand miles. I left in my black Mercedes (a terrible car to drive through any sorta weather at all). Later that Mercedes drove me into a ton of debt, but that’s not this story, that’s another story. The point I’m trying to make here is if you wanna know how to plan a road trip, you gotta know why you need the road (and the trip). That’ll determine where to go. But where you go means nothing. 


The city or town you use as your end point is only an excuse to experience the middle. Once you figure out which direction you’re heading and have your “vantage” destination, all the juicy shenanigans in between can take form, and that’s the good stuff. You don’t need any road trip ideas at all, they will appear. If you drive, things will happen (as the saying goes). 

Like the first night on that trip to Minneapolis when I pulled over somewhere in Utah without a clue of where to sleep…

How to plan a road trip: First, why are you going?

It was a desert. The stars were bright. The road was empty. It was an interstate but felt like a tiny highway. I had to get outta my head and talk my life out with strangers, and now I was all alone in the middle of Utah without sleeping arrangements. No problem at all. I’ll find a hostel.

I knew I had to go northeast (at some point) but I didn’t know anything else. For now I just need a city. 

My gut instinct told me that the closest hostel would probably be in the closest city, which was Salt Lake City like five hours away or whatever. So I just pulled out my phone and Googled: “Utah Hostels” and up popped the Lazy Lizard Hostel in Moab, Utah. At the time, I had never heard of Moab. Now when I meet someone who’s never been there I sell ‘em on it for a half an hour.

Doesn’t matter why it’s cool, what matters is I had never heard of it at the time but drove to the hostel nonetheless and found myself at a weird hippie house with a buncha musicians all drinkin and smokin weed in the back. 

On my way there I made phone calls to people I hadn’t talked to in a while and listened to an audiobook by Marianne Williamson on love and relationships. Yeah. Go fuck yourself. I hear you laughing. Remember she ran for president? Anyway, this was way before all that in the golden age of the early 2010s. Point is I got to the hostel after a few course modules and pulled into this hostel, and pulling into a hostel with a Mercedes looks mad weird. Like why wouldn’t I just stay at a hotel? Well cause I spent all my money on the car. The whole damn time I had that car it was impossible to negotiate with parking attendants.

Oh, the guy in a Mercedes wants a deal on parking? Fuck you. But they didn’t know I took out an absurd loan because I logged into Bank of America and up popped a question that asked: Want a loan?


How much?




So that’s why I got the car and was now stuck making massive payments every month. Anyway, don’t plan where you’re going, just start driving and connecting with the road. When you’re ready to stop, stop and sleep. You can sleep in many places (but bear in mind you won’t meet anyone at a hotel; hostels are best). But if you’re looking for alone time and you’ve got the money, stay at a hotel… any hotel really. Motel, hotel, AirBnB… doesn’t matter. Just find something within an hour’s drive and go. You can pull into a state park or rest area or Walmart parking lot and crash out in your car too (just make sure the Walmart owns the parking lot. Some Walmarts only lease the building. But if they own it, they allow car campers.) 

Sleeping is a small thing. What matters is you’re seeing the country and letting your emotions dictate your next move. That’s the secret when planning a road trip.

How to plan a road trip on Google Maps: pick a vantage point

How to plan a road trip on Google Maps is to pick a place that correlates with why you’re going. It’s like spinning a globe and closing your eyes. Seriously, it doesn’t matter where you’re going. Since I was desperate to get outta my head and meet other people that would make me forget about my ex, I picked Minneapolis, where I had high hopes of meeting the girl of my dreams, a hip hop publicist with dark makeup.

My thought: Don’t justify a better reason in your head about why you’re going. If some dude broke your heart and you wanna prove how free-spirited you are, do it. Be honest with yourself. Why the fuck are you going? Then you simply go to a place that might make you feel better. I call it a vantage point. It’s just a place that corresponds (lightly) with why you’re going out on the road. Wanna party? Head to Nashville or Savannah or New Orleans or Austin. Wanna immerse yourself in nature? Head to North Cascades or Glacier or Bryce Canyon. Wanna see crazy shit? Head to Carlsbad Caverns or Pigeon Forge. Want a serious adventure? Head to Costa Rica. Doesn’t matter really, just pick a place.

Planning a road trip – Don’t ever plan a route. 

No, the route will appear. Your vantage point is only there so you can see the big picture and let the details paint themselves. So, drop a pin somewhere, anywhere: Indianapolis, LA, Seattle, Mexico City, Anchorage, it doesn’t matter. Just drop that pin, and start driving.

I never planned on staying at the Lazy Lizard Hostel, but I knew it was closer to Minneapolis than I was in LA, so it seemed like a decent spot. 

Once I parked my overpriced car and got out and checked into my room and found a bed, I went outside to smoke a cigarette (thank God I quit that shit) and met this musician who stayed in my life for many years. He was a good dude living in a van. He was chasing his dreams of becoming a touring musician. I mean, he was a touring musician, but he wanted a bit more money, so he was doing whatever he could to make it happen.

I told him about my ex.

He told me about his ex.

He told me about his music.

I told him I worked with musicians in LA.

Instead of leaving the next morning, I decided to hike Arches National Park with him the next day. Then he showed me this weird coffee place where you had to make your own coffee and wash your own dishes and leave money in a jar. I stayed at that hostel for a few nights. He showed me all around town and introduced me to some locals. I had no idea where to go next, so I just thought… hmmm…

Maybe I’ll do another hostel? This was fun. So my musician friend recommended a place in Glenwood Springs, Colorado… 

Planning a road trip with no agenda

I didn’t even call the hostel I planned on sleeping at in Glenwood Springs till I had driven like three hours or whatever. But it was ski season there and the hostel cost like a hundred bucks a night. Fuck that, for a hostel? No way. But all the other hotels were tons of money, so I just kept driving. 

It turned into a snow storm. I could barely see. I was on I-70 deep in the mountains. Nowhere to even turn off. I found a bridge. It was off the highway. I hung out there. I parked and peed in the snow. Soon the snow subsided. I stayed at some Best Western I think. It’s all about letting go, and letting whatever happen. I needed freedom; not an agenda. I rarely know exactly where I’m going unless I’m taking a road trip to get to say a work convention or some shit. Then I’ll know where I’m staying (usually). 

Like the time I had to go to High Point, North Carolina for a big interior design convention for work. 

It was 2015 and I drove from New York. I decided to stop off at this cafe in Farmington, Virginia and criticize their coffee. That’s always the first thing I do to explore a new town: check out their cafes. Huge road trip hack: find cafes. that’ll teach ya everything you need to know about the town. I went to a cafe in Eureka, California once and it was depressing as fuck. So was Eureka. Anyway I was in Virginia and while I was at the cafe I decided to find an AirBnB based on how much further I thought I could drive. Pretty sure I can make it to Charlottesville. So I found an AirBnB in Charlottesville.

I got there and made herbal tea. It was like eight in the evening. I sat on a rocking chair they had in the enclosed patio that was attached to my room. There was a screen all around me so the bugs didn’t eat me and I could hear the breeze. The woman brought me fresh donuts and coffee first thing in the morning. 

See? High Point, North Carolina was my vantage point. That’s where I was going. I just so happened to stumble to Charlottesville. And when I swerved over somewhere outside of Glenwood Springs in the middle of a snow storm to eventually find a Best Western to sleep in, I knew Minneapolis was my vantage point. The vantage points just keep you on the right track. 

But where the track goes is up for grabs.

The moral of the story is find out WHY you wanna hit the road, pick a vantage point that’ll serve as a north star, then take as many wrong turns as possible. Be nice to everyone you meet. Things will happen. Where you’re going doesn’t matter… it’s how you get there that’ll quench your thirst.

Now here’s a story about that girl in Minneapolis…

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