I've been thinking about this for a while myself. The current place I work at is extremely remote-work friendly, and we have people in many cities all over the US and the world working from their homes.

One possibility is to take up a job at such a firm, and then do your traveling while you work. I think it beats stressing out about finding a new gig every few months, at least. It's also easier if you happen to travel in the same/similar timezone.