One can do that when they are younger, don't have a family or other commitments that would make those sorts of trips impossible (from your edit). If you are unable to do that, would you then just work all the time until you retire?
That's a great question. Honestly I don't know the answer. I'm actually married now with two young kids in suburban America, and with husband and wife (her ideals are pretty similar to mine) not-quite-content, and hoping to figure something out.
My ideal would be to do something like http://technomancy.us/, one of the big developers at Heroku, who is taking time off with his family to go do missionary work in rural Thailand, teaching his kids electronics, and meanwhile supporting himself selling custom keyboards.
