Chris Guillebeau

Want to know how to travel in style, just like the pros? We check in with frequent fliers to find out how often they fly, their favorite destinations and what they never leave home without.

Name:  Chris Guillebeau

Occupation:  Writer, Entrepreneur, Traveler

Hometown:   None

Residence:   PDX


Twitter: @ChrisGuillebeau


Pinterest: N/A

Bio: Chris Guillebeau travels the world and writes for a small army of remarkable people at His upcoming book, The $100 Startup, provides a blueprint of how 1,500 ordinary people quit their day jobs and created their own freedom.

How often do you fly? Constantly. Maybe 200,000 miles a year? I don’t keep up. About half of it is with OneWorld carriers and the other half a combination of everything else, including a lot of random airlines around the world. (A couple favorites: “Jubbah Airways” in Somalia and “Our Airline” in Nauru.)

How many countries have you been to?  183/193. These are official U.N. countries, not counting additional island stops or “sort of” countries like Taiwan, Kosovo, etc.

How many continents have you been to? Everything but Antarctica. (That’s coming up next year.)

Favorite American city? Tough choice. I love the energy of New York and the easy way of life of Portland, Oregon, where I live when not traveling. I also like Austin, Seattle, and San Fran. Further north, I love Vancouver.

Favorite international city? Again, hard to choose… but I spend a lot of time in Hong Kong these days. I’m not sure I’d want to live there, but it’s a familiar friend for frequent stopovers.

Least favorite country? Good question. Whenever I say anything even slightly negative, I hear from people who are offended. So let me say first that I’m sure Saudi Arabia and the Central African Republic are great places for some people… but for me, I didn’t care for them.

Favorite airline? Cathay Pacific. Singapore Airlines wins more awards, but their frequent flyer program is stingy with seats so I only travel with them once a year or so. With Cathay, I take at least 8 long-haul flights a year. In the U.S. I usually fly American to maintain my OneWorld status.

Favorite aircraft type? You (and maybe your readers!) will hate me for this, but I don’t actually pay much attention to aircraft type. Of course wide bodies are better than narrow bodies, and I appreciate the A380, but otherwise I think more about service and seat when I’m on board.

Aisle or window? Definitely aisle.

Favorite airport lounge? The Virgin Atlantic LHR Clubhouse is hard to top. I was recently in the Qantas First Class Lounge in Sydney, and that was nice too. And then there are the cabanas in The Wing in Hong Kong… I could go on for a while.

Favorite U.S. airport? Not sure I have one. Aside from PDX, I’m in DFW most often.

Favorite international airport? HKG for sheer familiarity. Runners-up: LHR (T5), JNB, NRT (T1), YVR.

Favorite hotel? These days most of my hotel stays are with Hyatt and Hilton properties. I love the Conrad in Singapore and the Andaz on Wall Street. I also stay in guesthouses, hostels, and more than my share of airport floor crashing.

Favorite cruise line? Windstar

Favorite island? Cuba. Runner-up: Solomons.   

Five things you bring on a plane? Macbook (writing you now from PDX-DFW). iPad. Magazines (New Yorker, Economist, Atlantic). Paper notebook. Compression socks.

What do you always seem to forget? Oops… I just realized I forgot my compression socks, and now I’m going all the way around the world. Too bad.

Favorite travel iPhone app(s):   Not sure.

Favorite travel book(s):  Most of Pico Iyer’s books. I also read and enjoyed The Sex Lives of Cannibals recently.

Most embarrassing/worst travel moment:  Too many to count! You name it, I’ve done it.

What’s your dream destination? I’ve been to most of the world, so these days I mostly think about places I’d like to revisit. That list includes Lithuania, Macedonia, Ethiopia, and Austria.

Favorite travel website(s) – besides, of course!:  Strange but true: I’ve met more people — and performed more trip research — through Twitter than anywhere else. Of course, is always the first stop.

Best travel tip: Having a duplicate passport has helped me a lot. It takes time and money to get it, but I don’t like having my only passport held up at the embassy of wherever thus preventing me from going anywhere else. Getting the second one made the whole process of frequent travel much more manageable.

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