Leaving home was the easy part. I’m at a hobo campground at the dead end of a lonely road at Bastendorff Beach, near the tiny seaside outpost of Charleston in the Great Drifter Heaven that is the state of Oregon. And I couldn’t wait to get here. I left my house on the East Coast, speed-walked impatiently through airports, got a car, and drove four hours, very fast, all to get to this: a parking lot next to a cold-ass beach, where a woman in a shitty sedan with no hubcaps is doing endless doughnuts in the mud and where the surrounding woods host a makeshift tent village for many, many meth addicts.

And yet I was in a hurry, and it wasn’t because I hate my home, or my family. It was just the itch. You know the itch. You wake up every day in a climate-controlled box, then you get into another box to go to work, then you sit in a third box all day just so you can afford bigger boxes and fancy crap to put in those boxes. Somewhere inside all those boxes, you get the itch to blow it all up. Leave everything behind. Live in the motherfuckin’ moment. Like Kerouac did, or Cheryl Strayed, or those people in those Expedia ads.

That’s why I’m here, about to board something called the Vagabus: a broken-down white school bus that a group of cloud-connected 21st-century hobos bought for $1,200 and then adorned with the cutesy Reddit alien logo. My guide through the farthest fringes of THE GRID is the famed Redditor known to all hobos as Huckstah (his real name: Steven Boutwell), who runs the /r/vagabond subreddit and who doles out advice to anyone online who is eager to get away—the bastard son of Bear Grylls and the Pied Piper. In addition to Huckstah, who is 34, we’ve got Ryan, who’s here illegally from Canada (WE NEED A WALL!) and who ditched his job running an IT start-up to live out here. He still dresses like he’s running an IT start-up: nice pants, clean black sweater. There’s Farkus, 27, a bearded mandolin player with faded tats and toenails that haven’t been clipped in months. And there’s Tilly, Farkus’s brunette traveling companion, a mellow Minnesota native who is new to the road and insists, somewhat unconvincingly, that traveling is in her blood.

“It’s not like I’m running away from any problems or anything,” Tilly tells me. “I’m just running away from the fact that I don’t belong staying in one spot, you know? I just got to go.”

Huckstah has a plan to drive the Vagabus all the way down to Argentina, and he would very much like for you to join him. He’s recruiting passengers through the Vagabus website, and he has the life he believes you may secretly want.

But like I said, leaving is the easy part. I came out here to Oregon knowing how it ended for Kerouac (dead from alcohol) and the real-life Dean Moriarty (dead from drugs) and that college kid from Into the Wild (dead inside an old bus…uh-oh). But maybe these kids have cracked the code. It sure seems like there are more of them than ever before, though maybe that’s just because they’re all on Reddit now. Or maybe it’s because the dream is finally REAL. Huck and the gang believe it is. Maybe. But only if you absorb the lessons I did during my one day—and one long, increasingly batshit night—out in the great wide open.

Personal snapshots from Huckstah’s life on the road/rails—that's him below.

You are way more of a pampered baby than you realize. Before I left home, Huck had warned me that nights on the Vagabus can get bitterly cold, and so he recommended a quick pre-stop at Walmart to pick up supplies: a sleeping bag, gloves (fingerless, for the authentic hobo look!), a knit hat, long johns, a big-ass bag of granola, a knife (for picking teeth, whittling, and self-defense), a water bottle, and a pair of wool socks. This, in theory, is all I’d need.

It also dovetailed nicely with my delusional sense of my own spartan lifestyle. I wear the same pair of jeans every day. I drive a Kia. Yessir, I don’t need much to keep me happy! But that’s a hilarious lie. As I was packing, I remembered I needed my phone. Oh, and a charger. And a toothbrush. And what about my ID and credit card? OMG and what about my contact lenses?! Do I sleep with them IN? And do I need some kind of bamboo mat for sleeping on the ground? Pillows! WHAT OF PILLOWS?!