travel jobs cayman islands

Travel jobs we have used to travel the world with no money

In 2010 when we researched all the travel jobs available we had no savings, so the plan was to travel and work at the same time. Or at least to travel for some periods of the year to support the rest of the time traveling. Back in those days, there were already hundreds of travel blogs and it looked like these bloggers were making some money out of it. But, researching it further, I came to the conclusion it was only a handful that really managed to be financially sustainable, and very few were teaching how to do it. The websites would give them some income but they had to do a lot of extra work, mostly offline and some online to balance bills and feed the traveling requirements. Due to that reality check, we embarked on exploring all the offline travel jobs options we had. Maybe you are not a digital person and still, want to travel without being connected all the time. Or maybe you are connected all the time and want to travel and be disconnected from your current real and digital world. Either way, we will show what we have done during these 8 years away from home. If you want to skip the offline world and go directly to the best online traveling job available then, by all means, jump directly to our article of the Best Online Job of today.

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Working as a cocktail bartender in London
Working as a cocktail bartender in London

How to make money and travel – our best options

It was this feeling of a potential struggle to maintain ourselves uniquely through blogging, mixed with the silly disbelief in our writing capacities, that led us to search for more traditional hands-on ways of how to make money and travel. We researched a lot at the time, everyone was saying that the two best ways to work and travel were working in the Hospitality business and English teaching. We believe this is still true today, although some other jobs became also quite frequent as you can check it many posts online sharing dozens of options. Matthew from Expert vagabond has an excellent article about travel jobs.

Like I said, there are many articles out there giving ideas of things to do, what I’m going to share is how we actually did it and what worked for us. If we were starting today with the knowledge we have we would do things differently, so writing this article will help you cut some corners, but at the end of the day we did very well, it just took a little longer than it could have taken.

If the best options were to learn about hospitality and teaching English we thought that we should go to London and master those skills. London is famous for exotic cocktail bartending skills, and it’s the land of English so no better place to learn how to teach the language itself. We packed our bags, left our jobs and moved to London. Luckily being part of European Union (at least in 2010, maybe by the time you are reading this Brexit has been implemented) we have free movement and free work conditions everywhere. When we talk about hospitality there are many jobs you can have, from hotel management to pastry chef. Bartending is probably the best for someone without any practice and that want to optimize work vs income. Cocktail bartender in the proper jobs can make loads of money, and at the same time can quickly get a job in any beach in the world. Bartending it was and off to London, our adventure had just started, and we were sure we knew how to make money and travel.

First Option – How to become a bartender and prepare to travel the world

You probably have seen the movie Matrix right? No, there wasn’t a how to become a bartender stunt from Neo, but there was something in the movie which it really fascinated me (not just one but many actually). I believe we are getting closer to accomplish it: the ability to inject knowledge and skills directly to our brain, just like the scene in the movie that they do it with the martial arts and helicopter piloting instant knowledge. I’ve heard a couple of podcasts and read some articles about this ability to accelerate your brain training. They call it neuro priming and you can check it out on the Startalk Radio Podcast too or even explore the guys doing it already, Halo Neuroscience.

Unfortunately, this is still not available for budget travelers like us which means we have to use old-school techniques: hardcore real-life practice. Even if you do a course on hospitality or specific bartending nothing will substitute real experience in your hands. And we say this because we want to make good money per hour. There are many bars and restaurants in the world that would accept you with no relevant background whatsoever, but then you are paid for that, and if the plan is to travel there is no time to climb the career ladder. If you really want to know how to make money while traveling with some decent paying conditions then you need to target higher pay rates for your jobs. And if you want to learn properly how to become a traveling bartender you need to move to a place where bartending has a high standard, typically in big cities or huge tourist spots.

Doing a Cocktail Bartending examination in Shaker UK, London
Doing a Cocktail Bartending examination in Shaker UK, London

We got our first jobs in London through agencies, but because we had no experience, they were terrible. Pretty soon, we felt miserable as hell. We had left our comfortable lives in Portugal, our safe and well-paid jobs for these supposed amazing traveling jobs. We cursed and regretted our decision many times. But we kept going and became resilient, a skill that has proven handy throughout our journey, and our life I would say. In the meantime I did a bartending course, to improve my skills and allow me to get better jobs. The goal was that, to learn how to work in proper bar jobs that would open doors in other countries. I found Shaker UK  but there were many options out there with the slogan “how to become a bartender in no time”.  I just chose this school because of their course schedule. The course was great, made good friends and learned a lot, not just bar skills but also knowledge about drinks. We learned everything about spirits, their production and history and that was pretty amazing.

Fast forward a month and I was working in a fancy cocktail bar close to Notting Hill in London. After a year I was ready for anything. I’m not saying you need a full year, we just had a saving goal in mind and it took us a full year to achieve in London because life is so expensive. With what I know now, a proper course and 6 months experience to give you some experience and confidence should be enough to land well-paying jobs abroad. I’m not saying that 6 months are enough to make you a great bartender, (if you are a bartender you are probably insulting me already), I’m not a great bartender and I never was. But 6 months will be enough for you to know what to do in a proper bar anywhere in the world even. Will you be able to do it as a pro with 10 years experience? Not at all, but you can be the third bartender doing some tasks only, but you know what’s going on. And so I became a traveling bartender, the coolest of all traveling jobs. You can check out our article about getting hospitality jobs in the Caribbean.

Second option – How to start Teaching English

We knew how to be a traveling bartender but we wanted to have a second option in case bartending did not work, so we moved on to what it was the second on the list of best travel jobs: English tutor. While living in London we looked for options to do the TEFL diploma, and there are millions. We chose i-to-i TEFL courses because they also had an online component, something that in 2010 was not so common as today. We did the weekend crash course and got our teaching diploma. We did not feel at any point capable of teaching any kind of English language, and unfortunately, during our stay in London, we had no time to practice. Maybe looking back to our experience we would have tried to have some practice before leaving London, or do a more comprehensive course than the 20 hours TEFL + 80 hours online study. Honestly, it’s just a way of selling you 100 hours when you don’t get much experience or practice. When you finish the course you don’t feel that you now know how to make money and travel. You feel more like: “how the hell am I going to survive with my current skills” We did have the hospitality skills to support us, and that was what supported us in our first stop: Cayman Islands.

After the Cayman Islands where we just did hospitality work, we moved to the second option of best travel jobs, and we started our teaching adventure in Nicaragua on a volunteering project we joined: The Peace Project of the Laguna de Apoyo. We started as support for more experienced teachers to give us some confidence and knowledge to do ourselves. Then when we traveled to Sao Paulo we got more teaching English jobs, but at this point we felt we could actually do some proper teaching.

teaching english nicaragua
During some classes, I gave in The Peace Project in Nicaragua

There are many destinations in the world famous for getting English teaching jobs that pay well: mainly in South America and Asia. The huge populations and growing globalization created a humongous demand for English teaching that is now taking the digital world by storm. We easily landed jobs in Sao Paulo, Brazil, I mean as easy as one can imagine. Sara for example applied to 10 schools and got 6 interviews, 60% job application success. Where in the world can you get this? Let alone traveling jobs, with so much competition. The pay wasn’t great but enough to live in the city, and that’s enough for almost everyone. Nobody goes to Brazil to save money right? Especially when the currency devaluates 25%, which happened during our stay there.

Better second option – Teaching English Online

We kept on with this approach of local travel jobs for 6 years, working in fancy American-style restaurants in the Caribbean or teaching English to skilled Brazilian multinational employees. To some extent, it worked out pretty well and our travels have been sustainable: we save during our “local” time, then we travel until we have to stop to save again.

The big issue with this modus operandi is time because one cannot do a round-the-world trip in 12 months or even 24. Initially, we planned 18 months but it’s been already 7 years. Well, we can’t complain about traveling for 7 years, can we? But in terms of traveling time, things get too concentrated in certain locations: 2 years in London, 2 years in the Cayman Islands, 3 years in São Paulo, you see where this is going. Again, we can’t really complain. Nonetheless, when we aimed to travel and live in all continents, we wanted to do that in a couple of years.

During all these years traveling, we met many people, lots of them were travelers and some were digital nomads. We always felt working online was not for us, it was just for some skilled people like web developers or famous bloggers, not the typical travel jobs. Speaking for myself, as I think Sara didn’t share my opinion, I always felt some envy because I knew that living off your savings makes you feel always uneasy, with a permanent countdown in the back of your mind.

Then, one day, when I decided to leave my job as a consultant in Brazil, I thought: why don’t I try to get online work with my skills? There were so many online work websites and we had already met fellow travelers working as translators or content creators, why couldn’t we do it?

working while near the beach in Portugal
Online work from anywhere. Some people think you are on holidays, but it’s just another working day

I decided to give it a try and looked for freelancing websites. First I tried my luck on websites like and and landed some not very well paid jobs of ghostwriting and translation. I know that in the beginning, you have to accept low paying jobs to create your portfolio and positive feedbacks so that you can go for better rates later. But I was really not excited about doing this kind of work, especially because it required a lot of time and effort for not that much money. A task that is really time-consuming is trying to get the jobs, you need to apply to them and compete with many people until you are able to land something. If I wanted to do this my full-time career, later on, I would have continued, but I did not have the inclination so I decided to try something else.

That’s when I saw an advertisement of Teaching English Online job and thought: Why Not? Have some experience, it’s online and apparently, it pays well, sounds exactly what I was looking. I got a couple of schools started to teach, and quickly realized digital life was an option, and a good one. I wrote an extensive article about being an English Tutor Online, and every single day I’m happy for this option. You can read the article why is it so good, but think just in time spent vs. income and you have a good idea.

Teaching in online schools gave us the confidence that there was another way: the digital way. We now use those jobs to pay for our travels so that we can work on our website. Maybe, in the future, we will be able to live full-time off of but, until then, we are happy to call ourselves Digital Nomads just by having the best online job you can have: Teaching English Online.

How should you find the traveling jobs right for you

No recipe is right for everyone, everyone is different and so traveling and finding work.  Currently, I’m very happy with our job situation, but it wasn’t always like this. Nevertheless, it allowed us to travel as we wanted, even if traveling bartender was never my dream job. (although I had great fun doing it) We went through a lot of the dozen jobs we have had, but after moving to online work we never looked back.

First, you need to decide if you want online or offline work, digital work means to stay sitting in front of your computer for many hours, which is not for everyone. Beside that there is no interaction while bartending, for example, you are interacting with the local community and learning a from them, which for us is critical on our travels. I do miss that human touch side of an offline work, but not so much to make me leave my online work. Especially because I manage to have many free hours, which allow me to explore the local life.

Another option you have is to start to do some online work on the side of your current main job. This way you can get some extra income, and test if you like it at the same time. When you feel confident about it, let it become your main income and skip the 9 to 5 life, or other offline work you may have.

If offline is your thing and you are good with people then check out our experience on how to become a bartender on the top of this article, I believe is probably the best option out there in terms of work vs. return. If on the other hand, you strive around a computer then try our article and database of more than 200 online teaching schools to get you started.

Good luck, and drop us a line if you need some more detail or guidance on these travel jobs, and check our ultimate guide for traveling healthy.


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