The business we run whilst we're doing this pulls in more than enough to support the outgoings; whilst it's not easy to set up a business that does this, it is more achievable than many people think.
It used to be possible for a good writer such as Samuel Clemens to simply travel the world and fund it by filing reports from abroad, or writing articles for travel magazines or travel guides. In a lot of ways what you are doing is similar.
However, do you know of anyone living a similar lifestyle that is not funded by writing, whether for the print media or its successor ? Perhaps by seeking out niche items in each place they visit, and selling them on ebay to Americans (perhaps through a partner still in the US) ? I have heard of people doing that in Argentina when that economy was worse off. Or by supervising the manufacture of something through mfgquote.com and its sales and delivery via the internet ?