Get frequent bonus micro-podcasts, travel updates, and a direct line to me for trip advice — all for the price of a beer. Patrons keep this whole operation on the road.
This has been a rewarding year so far. Covering new ground in South America has been on my mind for decades, and at last I reached the bottom. Back north in the US, I've been making the rounds, blasting through twenty-five states while revisiting friends, making a new backpack, and finding time to improve my Trip Hopping app.
Nineteen years ago I started this adventure, leaving New York City in the summer of 2007 with a giant backpack and pure excitement. The backpack has shrunk, but the excitement and the adventures continue.
As far as the year 2026, if you prefer to watch and listen, I put this video together while up in Wyoming:
In short, I spent New Year's Eve in Salt Lake City and then promptly hitchhiked to Texas. Dallas, in particular, simply because I had used my own app, Trip Hopping, to make the flexible flight search of: What is the cheapest flight from anywhere in the US to anywhere in South America in the next month or two?
The answer: $103 from Dallas, Texas, to Lima, Peru, in mid-January. Patagonia was a high priority of mine, so my journey started as a southbound one. I hitched down through Peru, into the northern Chilean desert, down through Patagonia's dense beauty, and all the way to the bottom of the continent.
Along the way I got my phone stolen, discovered that craft beer was actually pretty decent down there, and encountered all the random kindness and unique situations that hitchhiking frequently delivers.
By the way, if you're not listening to my podcast, Freestyle Travel Show, you can subscribe and listen anywhere. Here are the episodes from this year, talking about these very travels:
Listening to those will catch you up pretty well. If you want to hear and see even more, more frequently, you can support my travels by joining my Patreon page for the cost of buying me a beer every month. I record a short "micro-podcast" every few days while I'm hitching around exclusively for people like you.
Back to South America. Once I hit the bottom, naturally it was time to head north again. I hitched up the other side of the continent, by way of Buenos Aires, Uruguay, and into Brazil, before cutting west through Paraguay, Bolivia, and back into Peru.
Again, I highly recommend joining my Patreon, or at least following me on Instagram (@HoboLifestyle) to see some of the photos and videos from these adventures. The waterfalls I saw, for example, were Earth's finest.
Another cheap flight landed me in Florida from Peru. How cheap? Cheap enough that the airline, Spirit Airlines, went out of business just a week or two later. It's ok; more budget airlines will come and go.
I visited friends near Tampa, did bike food deliveries for a few days to cash up, made a new backpack in Mississippi, and road-tripped up to North Carolina. I hitched to see friends in Indiana and Michigan, over to Minnesota and Iowa, and eventually over to Denver for a couple pet-sitting gigs.
From there I hitched up to Wyoming to catch up with some family, and that brings me down to Arizona, where I am now. I popped down here, an hour west of Flagstaff, to catch up with some friends. My friend is hosting the Elevated Gathering in late September, something I highly recommend getting tickets to (if there's any left) if you're nearby and into marijuana and good vibes. I'll be there.
That about catches you up on my 2026 so far. As far as what's in store for my 20th year on the road... we shall see. I mentioned the Elevated Gathering in a couple months. And we'll be having a Trip Hopping collective before that, also in Arizona down in Phoenix—also something you might be interested in joining; just reach out.
Between now and then it's looking like California, maybe some casino stops to try and stack a little money. I've got a friend looking to go to Japan towards the end of October, so putting together a couple grand before then would serve me well to cover the next round of plane tickets and craft beer.
Good times keep rolling. Here's to another year of rambling ahead!
I'm Kenny Flannery, sharing my decade+ of travel stories and advice here on Hobo Lifestyle and the Freestyle Travel Show podcast.
I designed the BivyPack, which transforms between a backpack and a bivy tent while weighing less than 1lb. Now you can get your own, it ships to anywhere in the world.
Comments
Post a Comment