I honestly think it would be better to get 6-month or 9-month contract jobs, work like hell during that time, and then take some months off to see the world. And don't take your laptop with you ;-)
I have a bunch of Norwegian friends who did this. They would work March-September in Norway, when the weather isn't so bad, and then they would spend the winter months in Thailand, Bali, etc. I think this is the optimal scenario because work is separated from travel. When you're working, you are just working. When you're traveling, you're free to enjoy the places you visit and don't have to worry about deadlines, internet outages, etc