Chris Guillebeau is an entrepreneur, New York Times bestselling author, and traveler. We’re not talking take a trip to see your grandma down in Orlando — this guy’s been to every damn country in the world. (There are 193 of them.) Having covered all of those miles Guillebeau has uncovered plenty of strategies for those who want to start racking up stamps in their own passports. Below, he offers a few of his most important rules of the road.

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When it comes to packing, less is better. Guillebeau is all about packing minimally, especially when heading out for an extended period of time. He definitely does not claim to be a minimalist in every aspect of life, but always practices “less stuff = less stress” when traveling. This will then enable you to not have to check any baggage. Chris always travels with only a carry-on, to avoid having to check any baggage, which means less time time spent in airports and more time exploring your destination.


Once upon a time, Guillebeau was jetting to a new country most months of the year. Now, with his other gigs he has relegated the big travels to about a month a year. According to him one of the biggest things with booking super cheap airfare is just keeping your eyes peeled at all times. Like any of us, airlines make mistakes sometimes on prices — that’s when you pounce. Guillebeau says that if you spot an airfare that looks way too low, you should book it immediately at that rate. Airlines almost always will honor the rate that had been posted.

(He’s also found that US-based airlines consistently tend to have the best promotions and policies.)


Guillebeau says you can make travel cost as much you want it to but he personally feels comfortable planning to spend $1000 a month when traveling long term. He knows that people can and have done big trips on less and of course more but has found that figure is what works for him. “The point is to figure out what works for you and do that,” he says.

If you’re getting out of the country you will be engaging in air travel and Guillebeau found an interesting way to beef up airline miles before even stepping foot in the airport: credit cards. He had been using one or two a year that gave airline bonuses with spending, but went hog wild and applied for as many of the sort as he could one year. He says people had warned against it — that it would ruin his credit. But, he accumulated nearly 300,000 miles immediately and his credit score actually went up by years end. Of course, the only way to make that work is responsible spending. No Ferrari leases.


Guillebeau stresses that it’s important not to get too wrapped up in all the details surrounding your moves but to focus on making your trips the best they can be for you.

This post is a sponsored collaboration between Wild Turkey and Studio@Gawker.