Everything You Need to Know about Long-Term Travel

On the trail in El Chalten. Mt Fitz Roy is in the background.

“The real voyage of discovery consists not in seeking new landscapes, but in having new eyes.” 
– Marcel Proust

“I travel a lot; I hate having my life disrupted by routine.”  – Caskie Stinnett

When Jenny and I tell people that we spent nearly three months traveling through South America (and that we’ve also done multi-month trips through Europe and Asia), invariably one of the first things we’ll hear is “that’s so cool! I wish I could do that!”, to which we’ll respond, “you can!”. For some reason that takes most people by surprise, but it’s true: there’s nothing special about us and if we can do it, so can you.

Taking an overseas sabbatical is fun, exciting, and rewarding. I think it’s something that everyone should do at least once in their lives. There are definitely some challenges in doing so, and so I’d like to discuss how we were able to travel and how you can too.

Why We Travel

I think the first thing to discuss, before we get into the nuts and bolts of long term travel, is why someone would even want to do it.

The obvious answers to this are all the things you’ll see on this blog: amazing sights, exotic locations, delicious food, etc. But honestly that’s just the icing on the cake.

Did someone say cake?! Believe it or not, food isn’t the only reason we travel.

Have you ever been on a vacation where you really unplug and have a totally different routine? And then when you get back home you look around at your day-to-day life and think, “what is all this stuff? None of this is important. My job isn’t fulfilling, my closet is full of ugly clothes, and everything on TV is terrible! I’m going turn over a new leaf and decide what’s really important to me. I’m going to write a novel and hang out with friends and etc, etc.” Well, long term travel has that effect, but much more profound. It’s an amazing way to reset your life, to find what is truly important to you, and to expand your mind.

It’s also a wonderful way to learn about a different culture. You get to travel slowly, make local connections, and really get to know a place and the people who live there. Learning about those cultural differences helps you to look at your own life with fresh eyes. But at the same time you’ll be surprised at the things you have in common with people from around the world. It shows how we are all so similar, but can still learn so much from each other. The people in Thailand have a great expression for this: “same-same but different”.

It’s hard to overstate the effect long term travel can have on your life. It’s also hard to explain it. You just have to experience it for yourself.

Deciding Where to Go and For How Long

Once you’ve made the decision to try longterm travel, next comes the hardest part: deciding where to go! The world is a big place and there are a lot of great countries to visit. We get ideas from a variety of places including friends, books, magazines like National Geographic, and generally anything that piques our interest. Narrowing a trip down to one region is difficult but we try to remind ourselves that this won’t be the only trip in our lives and that it’s better to pick a destination than it is to stay at home because you can’t decide.

We’ve found two to three months is a great duration for us. Some people go for six to twelve months, and others spend years traveling with no home base. Everyone is different, but I would recommend a minimum of two months because it takes a few weeks to leave behind your old life and get into the rhythm of travel. Any shorter than two months and you’ll be on your flight home before you hit your stride!

Above the clouds in El Bolson.

Everyone is Different and Everyone Can Travel

We’re all different and what works for me and Jenny may not work for you. But you might be surprised to find how similar we all are and that by making a few different changes, the world of travel will open up for you.

Here are some profiles of people we’ve met on our most recent travels:

  • A middle-aged couple traveling the world for a year. When their daughter went off to college, they decided to rent out their home and head out into the world as well. Their daughter now flies out to different places in the world to meet them during her college breaks. They were unsure about how they’d find work when they returned to the US, but they’ve already been offered positions for when they return.
  • An 18-year-old backpacking through South America alone before she starts college. She’s on an extremely tiny budget and is funding her travels by picking up work at hostels via Workaway.
  • Two 30-somethings who work for different software companies. Their companies offer employees a three-month sabbatical every four years.
  • A teacher who asked for a one-year unpaid sabbatical. Her school granted her the time off and has guaranteed her a job when she returns.

We’ve met travelers who are young, old, male, female, wealthy, broke, black, white, employed, unemployed, single, married with kids, and everything else you could imagine. What they all have in common though is that they were willing to think unconventionally and try something new and scary. Some other things they have in common are amazing adventures, new friends, fun memories, and a greater understanding of themselves and the world around them.

Sharing a meal with new friends in Casa Blanca Valley.

Funding Your Adventure

We follow a two-pronged approach to funding our travels: we save up money while living our regular lives, and we use rewards points for free airfare and hotels.

There is a lot of information available about how to save money so I won’t go into that too much here. All I’ll say about it is that we try to live simply and deliberately. Once you have a goal in mind, such as taking a few months off to travel, it’s easy to focus on that and not waste money on frivolous things that don’t improve your life. Identify your goals and put aside a couple hundred dollars a month toward reaching them.

Now, about reward travel. An easy first step is to open up a Chase Sapphire credit card and use it for all your spending. After you spend $4,000 you’ll get 50,000 rewards points (at the time of this article) which is enough for a free roundtrip flight to many countries.

After you’ve done that, visit cardsfortravel.com a couple times a year and apply for the most appealing offers. Always pay your credit cards off in full each month, close them after a year unless you really like the card (we keep our Chase Sapphires), and be responsible with your spending. Since I started doing this years ago, my credit score has gone up into the “excellent” range and I’ve redeemed thousands of dollars worth of free flights.

If there was a frequent-flyer program for horses, we’d be in it.

Overcoming Common Barriers

Just because it’s possible to take an overseas sabbatical, doesn’t mean it’s easy! Some common reasons I’ve heard for not traveling are: “I have a job, I have a house, I have kids”. The solutions to these problems are simple. In order they are: quit it, sell it, give them away.

Ok, that’s a joke. I mean, it’s also a viable solution but I think it wouldn’t work for most people. These are all solvable problems though. Let’s take a look:

“I have a job”

  • Take a sabbatical. I know several people who have taken multi-month sabbaticals. Say to your boss, “I’d like to spend this winter in Australia. I’ve been meaning to do this for a while, and I feel like the time is right. I think that taking this time off will allow me to be more creative and more focused when I return.”
  • Work remotely. Again, many people have had success with this. “I’d like to work remotely from Paris. You know I frequently work from home and have been very productive with it. I’ll have no problem keeping East Coast hours and it’ll be like I never left the state.”
  • Quitting is the most obvious solution, and in some ways the easiest! The fear here is that you’ll run out of money (we’ll discuss that later) or that no one will hire you when you return. To that I say that if someone is willing to hire you now, then they’ll be happy to hire you when you come back. Don’t worry about having a “gap on your resume” because in my experience this is actually a selling point: it makes you seem like an interesting and exciting person.

In addition, here’s a great article about how long-term travel helps employees learn valuable skills they can bring back to their jobs.

“I have a house”

There are many services that will help you rent out your house so you can make money while traveling. Websites such as VRBO and Airbnb are two options. It’s also worth checking out house swapping services: maybe you’ll find someone in Tuscany who would love to swap houses for a while!

And don’t forget to reach out to your friends. You’d be surprised how many people in your network know someone who wants to rent a place in your neighborhood. We found a friend of a friend to stay in our apartment while we were away. Her company even picked up most of the rent!

“I have kids”

I don’t have any direct experience when it comes to traveling with kids, but I’ve met a lot of people who do. In general, people with kids seem to prefer renting out a house for a month or longer rather than backpacking around the world. But I think that’s a great way to travel and explore a new place. Plus, how amazing would that experience be for your children? They’ll always be able to think back to the summer they spent in Ireland when they were young.

“I don’t have enough money”

We associate long-term travel with millionaires and retirees, but have you ever sat down and figured out how much it really costs to travel? It’s not much. We spent less money hanging out with elephants in the jungles of Thailand than we do living in Boston. We’ve published our expenses for Asia, Europe, and South America. But you can travel for less or for more, depending on your budget and your taste.

Also, millionaires and retirees are two groups that are very smart with their money. Maybe emulating them isn’t such a bad idea…

“It’s scary or uncomfortable”

Travel can be scary. Especially on this trail in Purmamarca!

I think that for many people the problem is that it’s just too unconventional. Everyone around us follows the same script: go to school, get a job, buy a house, have kids, then retire. To go outside that script is weird, uncomfortable, and scary. What will my friends and family think? What if I fail? Will I never be able to find a job/partner? What if I turn into a weirdo living in a hippie house in Argentina?

But doing things that are scary and uncomfortable is exactly the point. This is how we grow and learn. Life is more exciting when we color outside the lines.

I’m a firm believer that if you live mindfully, try new things, maintain and grow your friendships, and are responsible with your money, then you can’t fail. Now, get out there and explore the world!

What do you think? Did we miss anything important in this post? Is the idea of long term travel exciting to you? Where would you like to go? Let us know!

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