When you hit the road for the first time there are a lot of things that are going to turn around and hit you back. Having a little preparation to deal with these things and some inspiration to keep you going is important.

Here’s what I read before hitting the road.

1. Vagabonding: An Uncommon Guide to the Art of Longterm World Travel

Rolf Potts is an amazing writer who has traveled all across the globe. He writes regularly at Vagablogging.net and has been featured in magazines like National Geographic Traveler, Outside, the New York Times Magazine and many more.

Vagabonding covers the basics of life on the road from before you even start. How to prepare for your trip, how to decide where to go, how to decide what to do when you get there, and much more. It’s less about specifics and more about learning how we want to travel in our own way.

This is one book that has stayed with me every step of my trip.

Buy it on Amazon.com before you get out there.

2. On the Road

Jack Kerouac was the American vagabond of the mid-20th century. Screaming across the country in cars from coast-to-coast, exploring cities and delving deep into life on the road as a spiritual experience, Kerouac has been the inspiration for many who roadtrip or travel.

Reading On the Road for the first time gives you a feel for the density of experience that vagabonding will provide. When you are out there on the road and hit a few bumps it is doubtfully as troublesome as the adventures that Kerouac went through.

I read this when I was in high school and have since read it over and over again. When you need a hit to jump start your passion again, this is one for me and hopefully you.

Buy it on Amazon.com and feel the rush.

3. A Walk in The Woods: Rediscovering America on The Appalachian Trail

Bill Bryson is one of my favorite authors hands down. His wit and the lightness with which he describes adversities he faces takes the wind out of that daunting first step.

When you set out to hike the Appalachian trail you are making a statement to yourself.

When you set out to vagabond across the country or the world you are making a statement to yourself.

It’s not about being a nonconformist or breaking from the mold necessarily, it is a personal pilgrimage to find out who you are and what you are made of. Bill Bryson gives us an insight into what makes him him.

Buy it on Amazon.com and take a hike.

4. The Four Hour Workweek

If Rolf Potts is the travel writer of the age, Timothy Ferriss is the entrepreneur who can show you how make the time to travel. This was the first book that really turned me onto traveling in a manner that made sense to me.

The Four Hour Workweek has a number of tools on how to divorce yourself from the incessant streams of information that we are bombarded with, create a business that will help fund your traveling, and a great deal more.

The title was purposefully chosen to create a bit of controversy, and yes it sounds a bit like a scam, but the ideas behind it are powerful and the motivation it gave me (one of the best slackers) to really work at redesigning my life is impressive.

Buy it on Amazon.com and see how many hours you want to put.

5. Your suggestions

What would a list be at only four? The fifth book is up to you, what else would you suggest to read before traveling?