A Look Into The Traveling Lifestyle

Guest Blog Post, written by Ken Flannery

Five summers ago I left New York City in favor of a traveling lifestyle, I rarely stay in one place more than a week and everything I own fits in my backpack.

I spent the first few years exploring North America, as far up as Alaska and as far south as Mexico City. This continent alone has many lifetimes worth of beautiful places to see and adventures to be had, from hiking the mars-like landscape of Southern Utah, snorkeling through the coral reef in the Sea of Cortez and parading around the non-stop party that is New Orleans. I’m constantly falling in love with places, people and moments.

I discovered hitchhiking early on and the world opened up into something even more amazing than what I’d been romanticizing in my pre-travel dreaming. Far from the axe-murdering media conception, the roads have been full of generous, curious and interesting drivers happy to get me towards the next destination, and in some cases, spark a new adventure entirely.

Last year I was able to get some flights together to start seeing more of the world, starting with New Zealand. This was the perfect way to kick it off, it’s an incredibly beautiful country with plenty of opportunity for hiking across diverse landscape of beaches, forest, mountains, glaciers and even getting lost in farmlands.

At the start of the trip while hiking along a remote beach in the north I’d taken my KEENs off to run barefoot into the waves, after a minute of splashing around I turned back to the beach just as a huge wave was attempting to capture my only pair of footwear. A future of permanent barefootedness flashed before my eyes, but luckily I was able to dive in and save one shoe and then the other.

That pair held up well for hundreds more kilometers of hiking through New Zealand, on to Australia, Southeast Asia and eventually over to Europe. It was an amazing year, I even got picked up hitchhiking by a millionaire who let me fly his helicopter and two seater performance plane doing barrel rolls and the like.

Once back in America I’ve kept it going, there’s still so much to see. A girl I met in Australia flew over excited to see the country and travel as well, we spent four months traveling together. We hitched from California to New York to the Florida Keys, then west again through New Orleans to the Grand Canyon and down into Baja, Mexico. Every step of the way we encountered great people and stunning scenery.

Money has proven to be far less important than I originally thought it might be, but over the years there have been some odd jobs that seem to pop up right when I need them. I spent a couple days helping on a bottling line at a brewery my friend works at in Oregon, I gave a ski lesson in Utah and I’ve helped out a few times during harvest season on different farms.

Overall it’s a pretty inexpensive and exciting way of life. Hitchhiking and sometimes just walking are free ways to get around land (and I’ve since discovered the possibility of hitchhiking on sailboats for getting across oceans), and instead of hotels or hostels, I use free hospitality websites like CouchSurfing or simply camp. Other than being inexpensive, this way of travel offers richer experiences and seems to be far more immersive.

Traveling is addictive, there’s always somewhere new to go. Summertime is particularly exciting since there’s so many more people on the go living their adventure, it’s great to link up for a while and share the new experiences.

I tend not to plan too far ahead, the best opportunities are presented spontaneously, so there’s no telling what lies ahead this summer and beyond. All I can really be certain of is that it’ll be full of good times, so here’s to another five years.

You can follow my travels on my site, HoboLifestyle.com.