Had the opportunity to travel to Buenos Aires, Argentina for two weeks, so I asked for my paid vacations and that trip changed my mind. I've never travelled at my age (22), so when I was back and in only one month I quit my job and start selling all my stuff I bought for 3 years. In the meanwhile I started to look for more freelance projects, and just two weeks before I took the plane - I had already bought my ticket - one remote job position was opened for me. Lot's of benefits like good salary and a brand new laptop, and they agreed that I was in another country and I was going to be traveling through all latinamerica.

One year since that, I was in Argentina for the whole year - I have really good stories. One month ago I arrived back to México, I still have my remote job position, I'm using my extra hours to have more freelance projects and I'm saving everything I have because I'm planning to go to Central America in August (Nicaragua, Costa Rica, Panamá, Colombia, Ecuador and Peru).

The things I learned from this experience is that traveling isn't that hard, you just need to plan ahead. You can decide what kind of traveling experience you want. My sister right now is bagpacking from Buenos Aires and she's right now at Ecuador, she's selling jewelry and food on each city she arrives. In the other hand, my kind of traveling involves a stable job, lot's of food and a good place to sleep and work. But that's your choice, there are different flavors for different people.

Interested in any replies people might have.

My plan for the next trip is to travel in between contracts and then settle down for a few months at a time whilst working. Hopefully that will allow more focus.

Edit: Actually I like gexla' idea above - pick a comfortable home base to work in and travel to nearby areas/countries in between contracts.

- Move to each city for 1 month (allow immersion in culture)

- The place needs to have privacy & wi-fi (no shared hostels)

- Use meet-up/expats/dances to meet people

- Research each city before hand on things to do/currency/language barriers/transportation (Austria, for instance, doesn't use Google maps)

It was one of the best times of my life, but it wasn't just pure happiness. It was very introspective, most of my time was spent alone, but I made so many life-long friends as well.

Loneliness/homesick is definitely a factor.

* travel to each event separately (my least preferred)

* have a couple of months off without pay

* work remotely for the couple of months while I was away

I'd earned a good rep at my company by smashing out the previous project on time/budget, so the working remotely was approved and all went well.

I liked it so much (escaping the northern hemisphere Winter), that I started my own consultancy and did the annual migration for the next 8 years. Most of that work was remote, so as long as I managed timezones, all was good.

We're able to spend a bit more and travel to more places as a result of having "real" jobs before our departure. This also gave us a taste of our day to day with our chosen professions and an excellent chance to make changes (based on real experience) if desired.

That said, I'd certainly recommend it for just about anyone who is interested. We've learned (basic) Spanish, tons of geography, and about the diversity of cultures in South America. We've also seen many amazing sites. I really wish this was more common for Americans.

The nice thing is, you can pull this off on a tourist visa.

I've been doing this since October & loving every minute. I still work full-time (remotely) as I don't have savings, but just being in new places has really changed my outlook & actually made me more excited/focused on the work I'm doing.

I freelanced for a bit via sites like We Work Remotely, then I found a full-time, remote role. I earn a SFBA market wage too, which actually means I am saving more being in countries with a much lower cost-of-living, than Sydney (where I was from) or SFBA itself.

In order to stretch our travel funds, we took local transport, stayed in hostels and campsites, and ate street food. Somewhat proud of the fact that we lived + traveled on $30-$90/day for more than a year.

For me, the best part was taking the same buses and trains as the locals. It gives you a glimpse into their everyday routine and also makes it easier to start a conversation.

Coming back and restarting income took a while though. Mainly because of personal preferences on the kind of work... ultimately just ended up doing the same kind of work that I left (frontend development).

Thinking of doing it again this year, but too scared to abandon income yet again. Might just try remote work this time.

However, most countries require an obscene amount of paperwork to stay there for an extended amount of time (as in 1-2 years).

Are there any countries where such a “working vacation” is possible? My family (spouse, one child) would be coming with me, so that complicates things somewhat (New Zealand, for example, will let you stay for a while but only if you’re under 30 and have no family with you).

I prefer somewhere in Europe. My second preference is somewhere in South America.

Have any of you done this? If so, can you share your experience? Thanks!

The moral of the story is, never lose your momentum, and always tell your clients how much you love them. Now if you'll excuse me, I'm going to go get drunk and cry.