About Kenny


Hey everyone! I'm Kenny Flannery, I started traveling in 2007, I've been living out of my backpack ever since, hitchhiking around the US and the rest of the world. I started HoboLifestyle.com to share my stories and advice, then later started the Freestyle Travel Show, a free podcast for people who want to listen to stories and advice as I'm on the go.


PayPal: HoboLifestyle@gmail.com (for those wishing to leave a tip or encourage my travels).
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Meet Kenny: This is a form for anyone who'd like to host me if I come through their town, grab a beer, offer a ride or anything like that.

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Questions I'm asked regularly

Where are you from?

I grew up bouncing between Connecticut and New York, mostly Connecticut. There were a couple stints of Utah and Maine thrown in there. After high school I moved near Orlando to go to an audio school, then back up to New York City, then eventually got bored with being stationary and started traveling.

How long have you been traveling?

Since the summer of 2007.

This whole time?

Yes. The longest I've been in one place in this time is just over a month.

How do you afford to travel?

It doesn't cost much, in fact it's more expensive to stay in one place, rent and whatnot.

OK, but how do you make money, do you have it saved up?

I don't make a lot of money, some odd jobs here and there.

Then how do you support yourself?

My lifestyle doesn't require much cash. I eat cheaply and travel freely, meet generous people and never turn down a good meal or a beer. Student loans can throw me a curve ball sometimes, but I work them out one way or another. Once I had $20 in Vegas and a video roulette machine turned it into $240, barely enough, but that paid the loan that month. Other times odd jobs have presented themselves, anything from an hour digging a hole to a few weeks helping with harvest.

You can read my post Spending and Making Money During Extended Travel to dig into that some more.

How do you afford to get around?

Most of the time I hitchhike.

Isn't hitchhiking dangerous?

There's a better chance of getting into a car accident then getting picked up by a serial killer or some such, hitchhiking's good times.

Do any weirdos pick you up?

That's what I look forward to, but they're only weirdos until you get to know them. Most of the time, though, the people picking me up are just generous good spirited people. Some used to hitchhike "back in the day", others have never picked up a hitchhiker before and wanted to give it a shot. Some are just looking for someone to talk to on a long drive, some people go out of there way to help a hitchhiker get to a better spot.

I write a lot about hitchhiking, but you check out my hitchhiking page to get started on tips, info and links to stories and videos.

Where do you sleep?

Wherever seems to be the place to be. Sometimes camping, sometimes with friends or family, new friends or I use couchsurfing. I also wrote a post called Where to Sleep While Traveling.

What's couchsurfing?

CouchSurfing.com, it's a website that let's you find locals who will let you crash on their couch or spare bedroom for a night or three. It's all free, you meet someone awesome most of the time and there's millions of people doing it across the globe. There's also new sites like TrustRoots.org that function in a similar way.

I have a whole episode about hospitality networks on my podcast you can listen to.

Isn't that scary, strangers and stuff?

No. It's awesome. It's safe. Have a good time!

What do you carry?

Clothes, a sleeping bag, some camping stuff... I wrote an insanely detailed post about this if you're really interested, Ultralight Packing Guide for Freestyle Travel.

What's your favorite place?

Depends on my mood, time of year, who I'm with, bla bla and yes. Flagstaff is a great town, Zion (southern Utah) is incredible to see, Chico is a cool community, New York City is always a happening place with good friends, Philadelphia has great food and bars, Las Vegas is a clusterfuck of insanity, Alaska is wide open, Vancouver has a lot of flavor and options, Savannah let's you drink on the streets, Jackson Hole is raw beauty, Belgium's got tasty beer, so does a lot of the USA these days, New Zealand is a traveler's paradise and there's plenty of other great places.

Are you hungry?

Always.

You want a beer?

Of course, thanks!

When are you gonna stop traveling?

I haven't thought that far ahead.


Those are the typical questions I'm asked. I love this lifestyle. The travel, the hitchhiking, the empty calendar that can be filled with endless anythings - it's all good. It's not about any one of those aspects entirely, it's about going with what's going, just loving it all. I meet people all the time with the spirit, more and more, some travel heaps, some not at all. They all got it. Life is good.



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