Travelling life: Chris Guillebeau

The American writer and entrepreneur tells us about the discoveries, strategies and destinations - including the UAE - that feature on his discerning travel list.

Chris Guillebeau often uses air miles to upgrade his flights. Stephanie D Zito
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Chris Guillebeau is an American author and entrepreneur based in Portland, Oregon. A former columnist for The National, Guillebeau visited every country in the world in the 10 years leading up to 2013 and became an expert in the art of "travel hacking", which involves accumulating huge numbers of air miles and hotel-stay points, facilitating cut-price and often free travel. As well as writing about this in books and a highly successful blog, Guillebeau has published four books, including The Art of Non-Conformity, The $100 Startup, The Happiness of Pursuit and most recently Born for This, about how people can find or create the job of their dreams.

What is your favourite destination?

I enjoy travel for the sake of travel. I like coming and going as much as I like being somewhere. If forced to choose a single spot, though, I’d pick Sydney, Australia. I return every year and it feels like a second home.

How often do you travel, and why?

I travel at least once a month, usually for a week or more at a time, to a total of at least 20 countries a year. Some of it is work-related, but I also travel for life itself. I get restless when I’m not on the road.

What do you like about travelling?

The mash-up of foreign and familiar. The disorientation that comes from flying 10 hours to another part of the world and stepping out into a different culture and climate. The sense of possibility – anything can happen, and everything feels new.

Is there anything you hate about travelling?

There are the usual grievances, but, honestly, they are minor trade-offs in exchange for all the gifts that travelling provides.

Where was the last place you went for a holiday?

I don’t really take holidays. Don’t get me wrong – I rest and relax, and I go to beautiful places all the time. But even when I’m there, I’m still working on various projects. Being totally offline doesn’t work for me; I have no desire to completely disconnect.

Do you prefer luxury or simplicity?

I’m not sure they are opposing values. I appreciate nice things like flight upgrades and comfortable hotels. But I don’t like a “hey, look at this” design style or approach to travel in general. Sometimes I’ll stay in a hostel one night before checking into a four-star hotel the next day.

How do you research your trips?

For a long time I used guidebooks, and I do think they can be helpful. Now, though, I do very little advance research. Sometimes I’ll identify one or two things I want to make sure I do. Everything else is flexible. I also started taking walking tours. You can find them in most cities, and they are a very easy way to jump in and learn a lot about the city from someone who lives there.

You have visited every country in the world going by the United Nations definition. Are there any other places or territories that you are keen to visit next?

Definitely. I went to Iran before, but I’d be the first to say I didn’t really explore it. I’m hoping to take a more extended trip soon.

What do you think of the Middle East? Do you travel to the GCC much?

I greatly enjoy visiting the Middle East and often visit the GCC. I come through Dubai, Abu Dhabi and Doha at least once a year. I especially enjoy flying Etihad and Emirates whenever possible, and both airlines have flexible layover policies. Venturing more off the beaten path, I like Lebanon a lot, but haven’t been there recently due to the security situation in nearby countries. I look forward to returning at some point in the future.

What do you always take with you on trips?

I’m pretty basic. Unless I’m going somewhere with an extreme climate or for some special purpose, I pack the same clothes for almost every trip. I always have my MacBook Air and iPhone, but I also always have a paper notebook that I use for journaling and writing down project notes. Also, I have a bad habit of leaving things behind in hotel rooms or on airplanes, so I try not to take things I can’t afford to lose.

You became famous for your system of ‘travel hacking’, allowing people to travel using points and miles. What has been your best upgrade so far?

Very recently I had a “dream trip” where I travelled from Sydney to Abu Dhabi in Etihad’s Apartment, which is like First Class, except bigger and better. The suite includes a sitting area the size of a couch, a lie-flat bed, a completely private compartment and even an on-board shower. The flight is normally very expensive, but I booked it using 60,000 American Airlines miles and just US$35.40 (Dh130) in taxes. Not bad!

What’s your best travel tip?

Anyone can take advantage of the more generous mileage programmes in the United States, no matter where they live – and you don’t have to fly on American carriers to earn miles. Emirates, for example, is a partner with Alaska Airlines. You can purchase Alaska miles and use them to redeem in premium cabins on Emirates for far less than the normal price. At least four times a year, they have a discount of up to 50 per cent off, making it even more affordable.

Where do you call home?

When I’m not travelling I live in Portland, Oregon. But I also think of “home” as a transitory place. I love returning to cities and towns that I’ve been to before, but still have more to learn about. I’m constantly looking forward to the next trip, and then the next one after that.

Where are you going next?

I’m currently on tour in North America for my new book, so it’s one city per day for a while. Once that’s done I’ll be planning another round-the-world trip, visiting (among other places) Korea, New Zealand and Chile.

Born for This is published by Penguin Random House and is available through Amazon.

Read this and more stories in Ultratravel magazine, out with The National on Thursday, May 19.