Is it possible to make a decent income from travelling the world?

For most people trying what you propose, making money while traveling, is not possible. Luckily, there are plenty who prove this just a rule of thumb, not a hard law.

Yes, it's possible to make enough money from a vlog, a blog, photography, professional articles or travel advice. But it's very hard to get started, and no real shortcuts to make it big. From my experience, it's really almost always a bit of luck and a lot of persistence that make for success.

That said, if you're indeed a decent developer, going freelance will allow you to be quite mobile. Perhaps even mobile enough to travel a lot. But what then helps is an existing client base who are ok with not always, if ever, meeting you in person.

I travel 3-6 months out of the year and have lived in a dozen countries or so in the last 15 years, pretty much always project related. I'm a developer. So, I'm not too distant from the type of life you seem to be interested in. But also know that the first half dozen years were rather tough. I got out of a well paying job to earn virtually nothing for years. But, I also firmly believe in the end it was worth it.

Pretty much all the projects I get are through word of mouth, which seems to be often the case when you're a freelancer, whether you're on the go or not. In the end, I'd say that keeping your client base happy or finding new clients isn't much different whether you're on the road or not. That said, clients tend to be wary of working with providers who they can't see or call into their office once in a while. The only remedy for that, really, is to consistently deliver quality.

Indeed, health care expenses outside of the US are reasonable in many places. International health care plans that don't cover the US, but pretty much do cover the rest of the world are often reasonably enough priced. And worth the money, in case something goes horribly wrong.

There is a term called digital nomad. This is someone who has no real home and is travelling and working using the internet.

As a software developer you can do a lot of work independently using oDesk or any other freelancer web site. Chiang Mai, Thailand is called the Mecca of digital nomads.

At least what I know it is inexpensive to get health insurance that covers travelling outside the US.

You may want to try Coworking. That's a way to get a workplace and to meet like-minded people from all over the world, many of them freelancers.

I am writing this, sitting in Coworking Las Palmas, which I found via deskwanted. Among my colleagues are other programmers (like me), a translator, a biologist (I believe), a serial entrepreneur, and architects.

Coworking spaces can also be useful to find clients. One of my current clients I have met at Loft to Work Madrid, other ones in Berlin at TheBusinessClass.Net and at Betahaus.

Often, I also work from public libraries. When using the Biblioteca Nacional de España in Madrid in 2011, I was pleasantly surprised to find a room with office chairs. It can't get much better than that!

Concerning accommodation, what has worked for me is Airbnb or similar for a week or two, then rent a furnished apartment or a room from a local. Coworking colleagues may help you. Personally, I don't like staying in hostels (too busy) or hotels (too sterile), and both are expensive compared to other options. You may also use Couchsurfing for the first days, which can give you good insight into local life.

This is a great question. I travelled for a couple of years by bike, and I made some money from web development, photography, writing and teaching English. My favourite out of these would be teaching because it integrates you with the community. Working freelance websites is quite alienating. Being a digital nomad is the best way to be IMO, and it is also flavour of the moment. Flavour used to be just going, but now its going and doing it sustainably. Hence books like '100 startup' by chris guillebeau try to figure out how its possible. However, I would say and agree with others that its a lot of work. Guillebeau in his book says its much easier to start the business before you leave, and run it remotely than start it whilst on the road. Web store fronts are more popular than high street ones these days so there is no reason not to set up any kind of business this way. Like anything to do any of this successfully takes time and patience and hard work. good luck with it, and post back with your experiences.

Another option is “volunteering” for room and board. Websites like wwoof.net and workaway.info can help you find opportunities. But research the rules for each country—it’s illegal in some for a noncitizen to work. USA, for example, considers room and board a form of pay. WWOOF actually advises you to lie to the border people. BAD advice!

1. Develop some course work that you can offer at nominal fees.
2. Create slide shows of the places you are visiting
3. Visit local schools/colleges to explore tutoring/slide shows.
4. Before landing in a city, make some linked-in friends. They can tell you the tricks of surviving in their city as well as offer some professional contacts.
5. Be prepared to live a very simple life away from the comfort++. I think this does not match with your basic requirement of decent salary.

These are my thoughts as someone who left a cozy job in India to start all over again in the United States as student. Good luck to you!