What do you do now? Trying to start a totally different career on the road isn't easy. You would be much better off taking an existing skill and trying to make it portable.
It doesn't even have to be something you get paid for now, just something you're good at. Something Internet-related would be ideal. Then you would have a constant address (your website or store). If you tried to do something that requires your physical presence then it could be very challenging to find new customers at each new location. Beware if you try the flea market/fair idea. Not only may it not coincide with your travel plans but they may also require you to hold a local business license.