Showing posts from 2019

Video: Hitchhiking to Florida after Mississippi

I hitchhiked from Mississippi to Florida. The trip involved some good rides, stealth camping, a "free" hotel room and some great…

"You got room for an owl?"

At the end of 2015, between Thanksgiving and Christmas, I hitchhiked from family to family, Wyoming to Southern California. In between wer…

Hopping: The backpacking beer adventure

Hopping is a new show where we'll be freestyle traveling from brewery to brewery, couch surfing and hitchhiking along the way. We'…

2019 Video Travel Update

2019 has been a busy year spanning across Africa, Europe and the United States. I've drank and brewed great beer, hitchhiked thousands…

Hitchhiking West for Thanksgiving

Waking up in the woods in Tennessee, or anywhere along any road, was nothing new. Even the feeling of not knowing where I'd be waking …

A Six-Pack of Hitchhiking Stories - my new book

After more than a decade on the road, my first book has been published.

"A Six-Pack of Hitchhiking Stories" is a collection of m…

Flowchart for those who want to travel

This is a simple flowchart to help you travel. You're welcome.

Two years with Google Fi around the world

Since switching to Google Fi (from Verizon) two years ago I've traveled to over 35 countries (listed below) throughout North America, …

Preparing the BivyPack for the Public

For years I dreamt and sketched up ideas for a backpack that would turn into a bivy tent to save weight and space while traveling. At the …

Hitching through the Midwest for New Orleans Debauchery

"Are your feet ticklish?"

"Not really," I replied with intentional disinterest; there's really nowhere positive th…

Travel Advice

Ultralight Packing Hitchhiking Where to sleep Spending and Making Money Freestyle Travel Show podcast Travel gear
See all travel advice

@HoboLifestyle on Instagram


Buy some of Kenny Flannery's photography here.

Hobo Travel Gear