Getting Started with Long-Term Travel

By Shannon Bradford

How many times have you heard a wistful sigh along with “Man, I wish I could travel the world”? If I had a peso (or a boliviano, or a penny, or a rupee) for every time I heard this, I’d be rich in several countries. Several times over.

Usually upon further probing, it becomes evident that some people don’t know what they want out of their travels. They just want to do it. This is a great starting point, but doesn’t get the majority of people very far along the path of accomplishing long-term travel.

So what’s the deal? If you’re reading this and wanting to start long-term traveling but don’t know where to start or even how to go about it, I’m hoping to pose some questions that might get the metaphorical travel ball rolling right toward the airport.

What do you want out of it? Are you looking to travel as a way to have a vacation-like jaunt in an exotic locale, or do you want to sell your house (and maybe the kids) and get the hell out of dodge? Are you interested in dedicating yourself to a specific cause, or do you want to fling yourself into a tiny town somewhere and work as a bartender for the next year? Do you want to say goodbye to everything you’ve ever known, or just take a little break?

There are more ways to long-term travel than you can shake a hiking stick at, and traveling is a great way to pair disparate life goals, as well. Somebody who has always dreamt of starting a non-profit AND zip-lining through the jungle might find a nice little situation in the mountains of Costa Rica with an English Language School. Inclinations toward filming documentaries + a burning desire to travel the Silk Road = one helluva travel project. The list goes on and on.

There’s a lot of ideas that can set our pulse racing, and that’s one of the reasons we have a lifetime on this planet – plenty of time to do all the things! But in the meantime, for this trip, only you will know your personal limits and desires. How important is comfort and security to you? How important is planning and infrastructure? Do you want a goddamned adventure or do you want some pampering out of it?

There are a lot of in-between points too, so ruminate carefully on this one. Taking a hard look at this, and identifying bare-bone goals (versus what sounds enchanting from the pages of a blog or travel magazine), will really begin to help frame your next trip.

How much money do you have or can you get? Finances aren’t everybody’s cup of tea, but it’s important to be realistic about what you have in your bank account. Travel eats up money, and a lot of it. Even budget travel, while vastly more economical than typical tourism techniques, is going to eat a hole in your savings.

Furthermore, plenty of twenty-somethings that are considering the leap into the unknown find themselves strapped with student loans and credit card debt. Every situation is unique, so you’ll need to figure out what sort of savings are necessary in order to continue paying loans while traveling. If you have federal student loans, you can talk with them to lower the payment or even defer for a time. The ideal situation would involve zero debt – and therefore zero worries about payments—but long-term travel is still possible even with monthly payments back home. But when this is the case, preparation becomes paramount.

So the question is, do you have (or will you have) enough money for the type of trip you want to take? There are excellent budget calculators out there (like this one and this one) that can help you get the ball rolling on understanding what, exactly, might be needed for your trip of choice. An around-the-world budget will look very different from a 6-month trek through South America. Figure out where you want to go and for how long– and then begin looking at the numbers.


Will you be working as you go, or will you have everything saved in advance? This tends to be the dividing line between types of travel in my book. Working remotely on the road has distinct advantages and disadvantages, as does the ‘hoard-the-cash-and-hit-the-road’ approach. Let’s look at both methods and the pros and cons of each.

Working AND traveling. Do you have a location-independent job currently, or can you convince your employer to let you take the work on the road? Do you have plans to launch something that will grant you the freedom to roam? Working on the road means you might not have a ton of savings but you’re pulling in a monthly income that helps finance the trip along the way. This is a huge boon – yet it means that you’re not completely in tourist mode. However, depending on the type of gig you have, this arrangement can facilitate long-term travel very easily. (I’ve been working remotely on the road for over two years for a USA-based non-profit.)

Pros: Allows you to travel mostly freely throughout the world. No real end date to the trip. Can usually be taken anywhere the internet exists/your business exists. Continuous source of money on the road. More security.

Cons: Slow internet connections can kill your productivity (and potentially enrage your clients/colleagues). Hard to predict where to find internet/how useful it will be once you find it. Adhering to schedules while in transition between cities/countries can be very difficult. Don’t get to always see or do as much as other travelers.

Just Traveling Around. Long-term and even multi-year trips are possible without maintaining a steady job. However, this involves a hefty savings in advance, which will require more time to work and save prior to beginning your trip. Plenty of travelers hit the road for an unknown length of time, picking up small jobs along the way (like at hostels or bars) to help offset expenditures. Some rely more heavily on roughing it, and the kindness of strangers. This can go on indefinitely, depending on how well you budget and what your savings looks like.

Pros: Not attached to a particular job or schedule. Much more freedom. Get to see and do whatever you want.

Cons: No reliable source of income. Dependent upon your savings, which will eventually dwindle. Possibly more stress about money/paying loans or bills back home.

And don’t forget to be realistic. It’s easy to look at the photos of professional travel bloggers and think, “damn, I want that life”. But do you really? Travel bloggers are usually bent over their laptops 75% of the day on the floor of hostels, strapped to deadlines and creative projects that sometimes have them doing everything but enjoying the humid summer breezes in Italy or the ancient temples of Central America. Yet they get the opportunity to travel the world, photograph it, and write about it; not to mention becoming some of the biggest travel influencers out there.

It’s also easy to hear about somebody’s friend’s cousin who launched an Around-The-World trip three years ago and got lost somewhere in Malaysia for 6 months and then finally eeked their way out of Asia and is sitting pretty in New Zealand on the beach slinging drinks for a decent amount of money. Sounds action-packed and legendary! Not to mention beautiful. But is that the type of trip you really want? Long-term travel means being very far away from family and friends, which can take a severe toll on some people. Yet sometimes it scratches a very, very deep itch that some of us harbor for years, and won’t be satisfied until we live it.

Looking at the tiny details of different scenarios that catch our eye help wipe away the fog of the ‘highlight reel’ effect. For years I was enchanted by people that had sold all their belongings and started a trip without end. But I also knew that being near my family is extremely important to me, so I needed to find a situation that enabled me to scratch all my itches. I found it, too – I spend most of my time in South America but visit a couple months of the year in the USA. But there’s still a part of me that gets swept away by those travelers who have been on the road, without a visit to home, for many, many years, even though I know that’s not something I actually want to do anymore. The romance of travel stories can sometimes cloud what we actually WANT.

This type of introspection enables you to get down to the nitty gritty of how you are going to launch your trip. There’s no right or wrong way to do this. Your preferences and interests combined with details only you know about yourself – like whether missing holidays is a big deal or not, and how many weeks spent in silent meditation are needed before you feel complete – will help you structure the trip of a lifetime. And even if you don’t know, that’s okay. Follow what your gut tells you. Once you get started looking at the details, you will be light years closer to making your dream trip – and possibly dream life – a reality.


Shannon Bradford is a twenty-something with a fondness for open air markets, ancient ruins and foreign tongues. She is currently living creatively in South America where she is completing several novels, mastering the Spanish language, and learning the ins and outs of the ex-patriot lifestyle. Check out her travel blog, Taking the Leap, and her professional page,

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