What happened with me between 2017 and 2021

Keeping up with my writing while amid my adventures has slipped as my regular readers have seen over the years.

I began my nomadic lifestyle in 2007, and for the first four years I'd write and post about my adventures as they happened. Slowly my posts slipped to writing about things that happened weeks ago, months ago, years ago, and then... it seemed daunting to catch up.

I still keep personal notes — cliff notes, if you will — but I miss the periodic coffee shop sessions where I'd delve into my stories while they were fresh in my mind.

My last post wrapped up all of 2016 — a step towards catching up — and now I'll summarize everything from then through to the very near present. It won't be as detailed as my normal posts, but it will allow me to get back in the habit of posting regularly.

Eventually (don't ask when) I'll release a comprehensive book of all my travels, and that's where I'll flesh out all the great highlights from these past years and all the years on the go.

I started my Freestyle Travel Show podcast — conveniently in 2017 — where I do in fact share my stories audibly and regularly, so I'll provide FTS (Freestyle Travel Show) links throughout this post if you'd like to dig deeper into some of the specific stories, as well as some YouTube links.

Let's get crazy and sum up all the miles, smiles, and craziness from the past several years.

2017 - Sierra Nevada Sparks an Adventure


I won a photo contest with Sierra Nevada Brewery which resulted in a free adventure tour trip of my choosing. I had many options, but seeing as they were going to send me the money for airfare as well, I chose a two-week package in Nepal as it was about as far as I could get.

We booked the tour for May of that year, and they sent me an overly generous Visa gift card to cover the airfare. That gave me four or five months to get there, the Freestyle way.

After making a brand new BivyPack prototype at my friend's place in Phoenix, I hitched on up to Las Vegas and caught a January flight to Hawaii for less than a hundred bucks. I spent a few weeks hitching around a couple islands, hiding from a helicopter while on a sketchy hike, finding beautiful campsites, and finding more reasons to want to come back to explore.


From there I caught the cheapest flight to Melbourne I could find. I spent just shy of a month hitching around Australia, catching up with friends, and making new ones all the way up to Darwin for the next cheap flight.

I think it was about $60 to get to Bali, where I hadn't been before. I dug into Bali for a while before hitching across Indonesia, couchsurfing from city to city on my way to Jakarta for yet another flight. Indonesia was dirty as hell, but the food was good and I met some interesting enough people along the way.

Next up was Cambodia, where Phnom Penh berated me with hookers, masseuses, taxi drivers, and everyone else on the streets trying to sell me something. I happily hitched to the coast where there was still some of this going on, but far more chill. Beers cost anywhere from twenty-five cents to a buck and a quarter in the rip-off areas.


I kept up the hitchhiking up to and through Thailand, hitting some familiar spots like Bangkok and some new places on the coast. I got my fill of deliciously affordable food as I made my way down to Kuala Lumpur in Malaysia for the actual flight to Nepal.

Kathmandu was dusty in the wake of earthquakes and road construction, but I enjoyed some of the bustle and also had a local friend there I'd met in California to show me the ropes. Then, the actual adventure tour began.

The funny thing about it was that it was a package for two people, but you'd be surprised how hard it is to give away a free trip to Nepal. People are all into their jobs and their lives and junk. Luckily, after posting a mysterious "event" on Couchsurfing.com, I got a response from one person.

I talked with an English girl who'd been on the road for about a year herself; she was currently at the San Francisco airport waiting on a flight to Kathmandu.

"So, I won this trip," I told her "it's a two-week adventure tour with rafting, paragliding, elephants, and all this other kinda stuff. Apparently the hotels and lodging are all covered and I think a bunch of the food too... at least I hope so. Kinda crazy, but if you're in then you can meet me at the first hotel in Kathmandu."

She was shocked, stoked, and suddenly I had a travel buddy for this random journey. It was a good thing too, as I'd expected there to be as many as a dozen other people all involved in this travel package, but it was just the two of us and a guide who'd pass us off here and again.

We toured around Kathmandu, then went around the country whitewater rafting, paragliding, riding an elephant, bungee jumping, and all kinds of ridiculousness as I ate cheap and delicious momos (like dumplings) for the few meals that weren't provided in the whole package.


By the end, she joined me in Kathmandu at my friend's place and we hitchhiked around the north in a little loop before parting ways.

From there I spent several weeks hitching across the border and down the middle of India. I ate spectacular food, couchsurfed from city to city, got forced onto a train by police, had my laptop stolen by a truck driver, and ultimately flew out to Dubai.

Dubai only lasted a couple days, couchsurfing by myself in a fancy highrise in the expensive city. Effectively, this was a long layover in the cheapest way I could find to land in Europe.

Instantly I fell in love with the little city of Sofia as I launched into another adventure on the European continent. I visited friends aiding refugees in Greece and hiked out to peninsulas I later found out was completely illegal. I skipped my way through country after country until meeting a new friend in Budapest who would guide us through a drunken mission to find his roots in Slovakia before just calling it a party all the way to Poland.

I got my kicks in Berlin and then hitched bit by bit to Portugal to take part in the HitchFest gathering. More running around through Spain and France and seeing a great friend in the Netherlands, and then great beer in Belgium before hitching through the UK onto Ireland for Flannery bars and the rest.


A flight back to the Northeast of the US set me off my typical hitching and North American rambling. I went on down the east coast, along the south through Biloxi and New Orleans, on up the middle of the country, and eventually to Wyoming, where I'd agreed to watch over someone's animals and cabins for several weeks.

By Thanksgiving, I was seeing some family in another part of Wyoming, and by mid-December I'd been through Vegas and San Diego and targeting North Carolina for Christmas. An incredible ride came in Phoenix with a guy who insisted on buying me a plane ticket, which made the skip across the country as easy as it gets.

2018 - Blowing up the BivyPack


After North Carolina I made my way to see my increasingly better friend in Biloxi. It was there that I made the crazy idea of doing yet another Kickstarter for my BivyPack, but this time I wound up being tasked to make about a hundred of them.

I spent the first part of the year in and out of Mississippi wondering why I'd ever decided to do such a thing. Sewing, sewing, and more sewing as I tried to escape the mechanical doldrums I'd become responsible for. I loved making BivyPack prototypes, but being in debt to dozens of people who'd already paid the money for the same one was driving me bonkers.

Eventually I escaped and got to my typical zigzagging around the US, highlighted by visiting sixty-one Portland breweries in a single day, hitching to NYC just for a fantasy football draft, and getting loaded in Tijuana.


By December I'd hoped on over to Spain where I visited the buddy I'd made in Budapest and then dropped in on a house of hackers working away on Trustroots — the hospitality site that has replaced Couchsurfing. Then, it was off to Africa for the first time.

2019 - Egyptian prison won't slow me down


I spent New Year's Eve with a new friend in Morrocco. I hitched all around the country before chaining a couple flights together to see my grandma at her home in Cyprus. In between, I made the nessecary stop to once again see my friend in the Netherlands.

My grandma's was peaceful, and I happily dug in for some weeks to see how she was living and enjoy the productive serenity.

It was off to Israel next. Hitchhiking there seemed common and easy, and the scenery was above my expectations. Crossing the border into Egypt, however, was a whole other matter.

It's quite the story and one covered in depth in what became one of my more popular podcast episodes, but let me sum it up real quick. They don't like people hitchhiking there. I had problems leaving the border with police, and there were checkpoints I had to pass and ran into issues throughout my first week inching through the country.

Eventually, a checkpoint collapsed on me, sending me into the bureaucratic system of police that landed me in one holding cell after another, confused and lacking the Arabic language to figure things out as my conditions worsened to the point of being in a packed room with other inmates fighting on top of each other.

Good times.

Listen to the podcast episode and you'll see I miraculously wound up on a plane for South Africa finally feeling free again. I got my kicks across that country as well, spending the bulk of my time cat-sitting in Cape Town making friends, and finishing my book, "A Six-Pack of Hitchhiking Stories."

Another promised house-sitting gig in Sacramento had me scrambling for the cheapest flight back. This resulted in a flight up to Germany and a hitchhike down to Spain to catch another flight to Boston and make my way from there. This makes perfect sense, of course.

After the gig at my friend's in Sacramento, my west coast rambling mode engaged, hitting my favorite spots like nearby Chico and getting down to San Diego.

I transported a friend's car from there to New Orleans, swung through Biloxi again, then did a looping hitchhiking maneuver to North Carolina and up to Michigan and back just for kicks. I put together some more BivyPacks as long as I was in Biloxi, then hitched on over to Florida to catch a Puerto Rico flight.

My buddy in Mississippi had easily talked me into joining the several-week trip over there with his family for Thanksgiving. I spent most of my time with them on beaches and in caves, and part of the time hitching around on my own for even more beaches and to explore if there was any kind of beer scene on the island.

From there it was back to the western US. By this point, I'd concocted an idea for a beer and travel show, and had my childhood friend on board with the idea.

2020 - The Backpacking Beer Adventure Begins


Just a few days before New Year 2020 I'd linked up with my friend in Las Vegas, armed with camera gear and the idea for a show I'd call "Hopping: The Backpacking Beer Adventure" where we'd hitchhike to breweries to interview them while drinking up.

We went from Vegas to Flagstaff and Phoenix, onward to San Diego, and north through California to Sacramento doing just that. He was pretty burned out by the end, but we had just enough footage to make it work.

He flew on back to New York and I hitched up to Chico where I heard the word "coronavirus" the first time and thought very little of it. I hitched on to the coast to see some other friends and wound up getting a week's work with the marijuana harvest.

My idea was to jump out of the US again, most likely to South America, so I figured I'd go to Biloxi to make another few BivyPacks to cash up and be closer to the cheaper flights. Having just made a pile of money trimming weed, I opted to catch a cheap flight rather than hitching, figuring every day I could be sewing in the south would mean more travel money, so no reason to spend a week or two by thumb instead.

As luck would have it, I landed in New Orleans in the thick of Mardi gras. I got my kicks, thoroughly, and skipped to Biloxi to make three or four BivyPacks before leaving the country. That's what I thought, anyhow.

Instead, the world started shutting down. I recall murmurs about China, then the NBA canceling games, San Francisco locking down, and finally even my buddy's tattoo shop right there in Biloxi was forced to close. South America was no longer an option, and it didn't seem like hitching around even in the States was going to go over so well immediately.

So, instead of three or four BivyPacks, I made about another twenty as I let a couple months pass going stir crazy, but happy that I was at least with good friends in a place where I could be productive. My editor for Hopping, who was working for free, also happened to suddenly have the time on his hands to start putting episodes together.

By the end of May, my buddy's tattoo shop had reopened and things seemed to be getting better. Meanwhile, my sister (in Wyoming) had bought my brother's car (in Connecticut) but hadn't been able to fly out and get it with everything being locked down, so I decided I'd hitch on up there and drive it out west for her.

I wasn't sure how hitching would go given everything that had just gone down, but I got up to New York just as easily as ever. I was pleased to see that the city was not littered with body bags as the news had been eluding to. I hadn't been used to isolation in one place, relying on the internet for information rather than just being out and about and hearing from everyone.

The parks were full of cheerful people, open container laws were being ignored, the sun was shining and the city was alive. I didn't stay long, however. Soon enough I was zipping my sister's "new" Jeep clear over to her in Wyoming.

I relaxed with family over there as the last of the Hopping episodes were released on YouTube, making sure everything went smoothly.

Shortly after the 4th of July, I got moving again. There didn't seem to be an end in sight as far as many other countries allowing travel, so assuming the worst, I decided I'd spend as much of these coming warmer months in all the northern states suspecting that I'd be relegated to the south come winter — and I'd be right.

I hitched throughout Montana seeing friends, hitting up Glacier National Park, and even accidentally breaking into an old women's house I thought I'd been in the night before, only to leave a note and then have to deal with the police. Again, there's a podcast and even a video to dig into that story.

I slipped through Washington to Idaho getting increasingly familiar kicks in Boise. I visited a good friend in Salt Lake, another in Denver, and scored excellent rides through Nebraska and Iowa to go see yet another great friend in Minneapolis. I went out of my way to see great breweries like Toppling Goliath, and ping-ponged from Madison, Wisconsin, on over to Kansas City.

I caught up with a friend there to see what kind of ludicrous shenanigans she was getting into, and by then it was September and I could sense the seasons preparing to shift.

I scampered through Arkansas, my thumb in full effect, and dipped my toes into Biloxi yet again. I bounced off North Carolina to my brother and all for Thanksgiving, then hitched the southern route through Texas to Phoenix before cutting up through Vegas for a night on route to a Wyoming Christmas and 2021 New Year's Eve.

2021 - The Adventure is Still Unfolding


My friend in Kansas City got me a ticket there, saving a cold and lengthy hitchhike. By this time she was in a new spot with new tricks, still digging into life and working her angles.

I made a jump to Florida from there, happy to have hobo warmth in January. I was in Tampa when their team won the Superbowl and figured I'd be slow-hitching my way through the state as I waited out warmer months and for southern countries to open their borders.

Meanwhile, the next season of Hopping was being discussed, and some funding was being secured to make it happen. With all these documentary thoughts in my mind, it reminded me of a friend I hadn't chatted with in some months and sent her a catch-up text just to see how she was.

She told me she was in the Bahamas, indeed filming a documentary herself. When I told her I was in Florida, she instantly suggested that I go to Orlando to pick up a camera and she'd fly me on over since it would be just as cheap or even cheaper than if she had it shipped.

I didn't hesitate on this offer and was over to her in less than a week. I spent a little time in Nassau, for the first time, taking in the mostly empty beaches and embracing the spontaneous magic that had occurred. Another flight had me back in Miami and I instantly got myself down to the Keys.

I hit all the breweries while I was down there and then started hitching and walking my way up the east coast of the state. I was hitting a brewery a day, sometimes five or six or seven. I was staying with friends some nights, camping most others. Some days I just walked, pausing only at breweries to drink and coffee shops to be productive. Sip and repeat.

I spent about a week in Jacksonville with a girl I'd initially met at a nomad base in Amsterdam some ten years ago. From that point I hitched clear to Pensacola in a day, by far the biggest day-jump in a month compared to my little walks and fifteen mile mini-hitches up the coast. I continued the brewery hopping for a day or so until walking over the border into Alabama after a pleasant sleep on an empty stretch of beach.

I jumped on over to Biloxi, where my friend was making some significant life changes. He and his wife were independently figuring out what was next for themselves. They were dealing with a rift between themselves, what that actually meant, and what might be next. There was talk of the house being sold, and action involving a camper that my friend intended to start roaming the country with.

And indeed the roaming began. He planned to go up to Maine, and conveniently, I was aiming for New York myself to hand-deliver the new camera equipment to my friend up there so he could learn how to use it before the next season of my Hopping show.

And now, this nearly brings us up to date (May 2021). I'll leave you with that for now. We did it!

Next up, I'll write about getting to New York and the epic yet dramatic and unexpected journey that was the filming of season two of Hopping that ended in Portland less than a week ago. And hopefully, from now on, I'll stay on top of writing about my adventures as they happen again.

Cheers everybody, I'll see you down the road.

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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.

I also wrote a fun book called A Six-Pack of Hitchhiking Stories which you can get on Amazon.

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