The secrets to traveling for months (or years) at a time

Long term travel. It’s a dream many of us have, but so few of us act on. Whether it’s a few months or a few years, most of us would love to wander the world without a schedule, discovering new foods, experiencing new cultures and meeting new people.

For the past decade, I’ve been lucky enough to spend between 3-8 months a year overseas. I’ve spent summers in California playing beach volleyball. I’ve country hopped around Europe. I’ve road tripped around Iceland and kayaked the fjords of Norway. I’ve been mere meters away from lions in Aftrica. I’ve eaten my way through the street food stalls of Asia. And I’ve watched the Olympics on the sands of Copacabana beach in Rio de Janiero.

Along the way I’ve met plenty of people who have embraced the long term travel lifestyle. What they’re doing varies – they might be writing a book in Bali, doing a yoga retreat in Hawaii, motorcycling across France, or hiking in the Himalayas – but none of them are lying by the pool in a resort for a week and then returning to their desk jobs.

When people discover how much I travel I invariably get comments like:
‘I wish I could travel as much as you.’
‘You’re so lucky your job lets you take that much time off’
‘I could never do that’

It’s not easy to pick up and leave. But it’s not as hard as you think it is either.

To help you on your way to packing your suitcase and buying that airplane ticket… Here are some solutions to the common reasons people give as to why long term travel isn’t possible for them.

I have a mortgage / house / apartment

Great. That actually makes long term travel easier for you, as long as you are willing to let other people stay in your place.

Have you considered:

  • Long term rental of your place. Business people who need to work in another city for a few months are great tenants. Someone moving to your city that needs a place to stay while they look for their own property is also a great option. Or you could simply go through a rental agency.
  • AirBnb. You can look for long term renters, or, if you have someone to manage your property for you, you can accept shorter stays as well. AirBnb lets you set the time period of your stay and you can vet the people based on the reviews other hosts have left.
  • House swap. There are a number of sites where you can list your home and people around the world can offer to ‘swap’ with you. Think of the movie ‘The Holiday’. Our family actually exchanged our home in Melbourne for a Villa in Thailand over Christmas one year. Best Christmas ever.

If you live in a first world country, it’s likely you’ll make a profit if you rent your home out which gives you more spending money for your adventures!

I have a car… and car repayments to make

No problem. It’s not just your house you can rent out. You know you can rent your car to someone too? I’ve done this a couple of times (once to a couple who wanted a car for winter so they didn’t have to bike around, and once to a friend’s mum who didn’t drive often but wanted a car available). I used to make this offer to friends through Facebook, but these days there are sites and apps that organise this for you. You could even rent your car to someone who wants to start doing Uber. Voila – you can make a profit on your car while you’re away too!

Note that if you are going on really long term travel of more than 6 months, you might as well just sell your car and buy another one when you return.

My job would never let me leave

Everything I’ll say here is predicated on assuming that you are good at your job and valued by your company or industry. If you’re not, maybe you’re in the wrong role or should think about building up some career capital first.

First things first… have you asked your company for long term (unpaid) leave? It’s incredible how many people assume that their boss will say no, and never even make the request. I’ve had a boss say yes to moving to a 4 day work week. I’ve had a company say yes to giving me three months off. I’ve had organisations that are happy to guarantee me an extra 4-6 weeks of unpaid leave a year. Other employees tell me I’m lucky, but the truth is I just asked.

Second, are you prepared to negotiate? When you start a job, or anytime you discuss performance with your manager, there are a whole host of non-salary things you can negotiate on. Often, managers are more than happy to grant you something other than an incremental salary rise. Have a think about what you value most – it could be:

  • Additional paid or unpaid leave each year
  • Moving to a 4 day work week or a 9 day fortnight
  • Working your full time hours across 4 days, and taking one day a week off
  • Working remotely sometimes
  • Flexing your hours outside of the standard 9-5
  • Getting more professional development opportunities such as attending courses and conferences

Third, think about what type of role you have. If you have a project based role, then your boss might be willing to grant you more leave at the end of the project, before you start a new one. That way, no one will really need you in the office so you won’t be as missed. If you don’t have a project based role, perhaps you can train your direct reports to fill in for you temporarily. Or you could job share with another person who is keen to work only part of the year. Companies have all types of different arrangements, it’s up to you to explore them.

Fourth, consider if a traditional job is the right employment type for you. Maybe you’d be better off as a freelancer or contractor? (I switched to freelancing and found I could earn my previous full-time salary in just 4 months of work, leaving me 8 months to travel.) Or perhaps you should start your own business?

Fifth, if you don’t love what you do maybe a complete career change is worth looking at. There are a ton of jobs that let you travel extensively (think coding, writing, graphic design, social media manager, life or business coaching, and motivational speaking). If you want to travel long term every year, not just once, it’s worth designing your career around that.

Sixth, just quit. I’ve done it three times already. If you are good at what you do it’s not as hard as you think to get another job. Forget about the economy, the sluggish job market, or frozen headcounts at companies. The fact is there is enough churn in the job market that if you’re good, you’ll get hired.

Note that if you have a business… refer to the saying that ‘If your business can’t exist without you, then you have a job, not a business.’ I’d also suggest reading ‘The 4 Hour Work Week’ for some great ideas on how to extract yourself from needing to be constantly present in your business.

Travel is too expensive, I can’t afford it

Short term travel is expensive, I completely agree. But long term travel… that’s a whole different ball game. Let’s go through the three biggest expenses that people think about: Flights, accommodation and food.


Forking out $1500 for flights for a one week trip, averages out to $215 a day for that trip. But the same expense for a 3 month trip… that’s only $16 a day. Changing your perspective makes a big difference when you are thinking about flights.

There are a ton of sites dedicated to helping you hack cheap flights, but my tops tips are:

  • Book a long way in advance, there are often crazy good deals
  • Travel between Tuesday and Thursday, these are the cheapest days
  • Figure out how to use your frequent flyer points
  • Be really flexible on dates, or even travel in the off-peak season

You have to get there, but the flights are a one off that once booked you don’t have to think about again. Get a good deal and go for it.


Accommodation can quickly become the biggest expense of any trip. There are two approaches you can take when traveling long term: cheap or free.

Cheap accommodation is pretty straight forward. Do either or both of the following:

  • Rent a place long term (1+ months). For example, in Berlin you might pay 100 euro a night for an average hotel. But you could rent a whole apartment in a great area for 900 euro a month, or a room in a shared apartment for 300 euro a month.
  • Go to a cheap country. In southeast Asia or South America the cost of living is so much cheaper than western countries you could easily get a luxurious place for far less than the cost of your rent back home.

Free accommodation relies on your ability to make friends. When I travel I don’t make a set itinerary, instead I go where I’m invited. This year I was in Europe and stayed with a friend in the Netherlands for a week. She had a friend in a different city who needed a pet-sitter for her rabbit for a week – so I went there next. Then another friend invited me to Poland and set me up with a place to stay for a week. And so on.

I guarantee you’ll have at least one friend or family member who lives elsewhere in the world who has invited you to visit them. When they offer – say yes. That’s you’re starting point. From there, make new friends, say yes to invitations, and tap into your Facebook network. You’ll be surprised at who offers to host you. I once had a guy in Beunos Airres host me for 4 days and I didn’t even know him, he was just friends with one of my Facebook friends. If you’re aiming for free accommodation, you’ll have to be more flexible with your plans.


Eating out gets expensive, but with long term travel you are staying in the same place for long enough that you can cook. You are also staying long enough that you might make friends with some locals who will invite you over for dinner!

You’ll also want to make an effort to eat at the ‘local’ places and avoid the tourist places. Not only will the food be better, it’ll be a lot cheaper too.

Working while traveling

A lot of young people combine work and travel as a way to see the world. Many countries offer working holiday visas (typically for people younger than 30) allowing you to earn an income while visiting a nation. If you’re over 30, you can look at doing some freelance work on the side while you travel. It’s a good way to extend your travels for longer without having to save as much in advance.

Those are the main reasons people give for not traveling long term. If you have any more tips then I’d love to hear them. Thousands of people are making it work, and if you want to see the world, then there is no reason you can’t too.

Before I sign off (and go back to my own travel adventures) there is one more important question you need an answer to:

What are you going to do with all your time while you travel?

If you are staying in one place for a while, then you’ll wind up with a lot of free time. There are only so many religious monuments and museums you can go to.

When I travel I always plan to do two things: something physical (for me it’s play beach volleyball), and some sort of project or study that I want to do. After much trial and error I find that’s the best combination. Something physical, and something mental.

A physical activity is an amazing way to make friends, connect with the culture, learn the language and of course not get fat on French croissants or Swedish kanelbuller. I’ve met people who are learning to dance, doing yoga, studying a martial art, joining a rowing club or hiking long distances. Pick something.

A project is also necessary. After a couple of months without using your brain you’ll start getting bored, regardless of how interesting your travel adventures are. For some people it’s as simple as writing a regular blog. Some years I do an online course (over the years I’ve done sports psychology, Seth Godin’s AltMBA, and my NLP accreditation). It could be learning the local language, or taking lessons in photography. It could be the chance you’ve been waiting for to write a book, start a podcast, learn a new subject, or go back to school. Aim to come back from your travels not just with stories of your experiences, but with more knowledge and skills than you left with.

If you’ve ever wanted to travel long term, I hope I’ve given you a starting point. It’s not easy, but it’s definitely not as hard as you think. Maybe in a year or two your friends will be saying to you:

‘I wish I could travel as much as you.’
‘You’re so lucky your job lets you take that much time off’
‘I could never do that’

Let the adventures begin.

September 21, 2019