Is long-term Travel for You?

Achieving the right mindset

Who hasn’t dreamt of ditching the corporate job, stuffing whatever will fit into a backpack and heading off to explore the world, destination unknown? For every person who actually does it, there are probably dozens if not hundreds of armchair travelers who have dreamed about it and inevitably backburnered the idea because life ― career, home, family ― got in the way.

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Personally, I’ve only done two semi- long trips: a three-month round-the- world (RTW) jaunt and almost three months of overlanding Africa from top to bottom. While I love reading travel blogs where headings are something like “Day 483: Kathmandu,” I’ve often wondered what it takes to really travel long-term, something I would define as at least a year continuously on the road, without too many stops of a week or more in one place. How would one go about arranging the logistics? What happens to your job? Your belongings? How difficult would the transition be to re-enter society when you come back? How would potential employers view a long gap in work history?

For this column, I tapped Jeremy Jones, author of The Long-Term Traveler’s Guide (available in print or e-book from Amazon and iTunes). Jeremy has visited 66 countries so far (with Sri Lanka in the works), many of them on two long-term trips he did in the past six years.

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In his book, Jeremy talks about the sensibility of long-term travel. “One year is a great milestone as it is the perfect timeframe to see a substantial amount of your must-see destinations list as well as ample time to really begin understanding several regions around the world.” As if I needed any encouragement, Jeremy also makes the case that in a year, you can see 91 cities (with a four-day average stay), 23 countries (four cities per country), eat 1,095 meals and amortize airfare down to dollars a day.

In the book, you talk about various hurdles (mental, physical, financial) in getting a RTW trip off the ground. What was most challenging for you and how did you overcome it?

Jeremy Jones: » On my first RTW trip it was definitely leaving Angie (my wife). We were dating at the time and I had started to plan the trip before we got together in 2009. After a lot of talking we decided I would do half, and we’d do the rest on a future RTW trip (the one we just finished), but dealing with the emotional hurdle of leaving loved ones can be quite hard. I am thankful that by the time I took my second one she was with me and our families assumed it was business as usual with us and didn’t worry! «

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One of the first things to decide about long-term travel is who you’re going to travel with. Jeremy makes a compelling case each for solo travel, traveling with close friends, spouses and what he calls “30 Minute Friends” ― people you meet while on the road. Personally, I’ve had decent friendships not survive the crucible of travel which puts you in strange and often stressful situations where unlike home, it’s not as easy for everyone to simply go their separate ways after a night of fun. On the other hand, it’s nice to have someone to share expenses with and enjoy meals together.

Many people would find it daunting to be around their partner all day for days on end. Do you think travel has strengthened your marriage? In what ways?

JJ: » I love the Bill Murray quote that recently came out: ‘If you’re in love with someone, travel the world with them and if you still love them, marry them at the airport the second you get home.’ There is a lot of stress associated with being on the road, and most of ours came when my backpack was stolen in Peru towards the end of the trip. I can’t say we ever had many issues from being together so much, but whenever we were needing some free time we just went off and did our own thing without issue. I’m actually more worried about being apart now that we’re home since it was so much fun on the road! «

I would think one of the biggest challenges of long-term travel is simply arranging the logistics of leaving your life behind. It might be easier if you’re living with family, but the thought of finding what to do with your car, apartment/house, belongings just seems daunting to me. Personally, the few days before a trip of even one or two weeks is a flurry of getting work done, making sure I’ve rescheduled things, etc. so it’s hard to imagine sorting your life out for an entire year. Have you experienced any negative backlash when telling people that you’re long-term travelers?

JJ: » If I had a dollar for the number of people who asked “what will you do without a job?” I would have enough money to never need a job ever again.
It is a really odd thing to hear because many people just don’t understand that you can go without working 30 years straight. We also get a lot of people who assume we’re trust fund babies who had their parents pay for it, which couldn’t be further from the truth either, as we worked for several years to save up for it. «

In an upcoming column, I’ll continue this discussion with Jeremy and we’ll get into what type of planning is best for long-term travel (for example, how far in advance to arrange lodging, flights or maybe nothing at all!), ways to save up for a RTW trip and best practice for securing visas and avoiding scams. In the meantime, read more of Jeremy and Angie’s adventures at




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