I'm currently in the process of leaving work now to take 3-6 months off to learn Japanese and maybe work on some of my own project ideas if I feel like it. Although I still have a little doubt about the switch, it is reassuring to see someone who has taken long breaks as well.
Yes. During my heaviest years of contract/travel/contract/travel, I found I came out between $10k and $20k ahead in savings at the end of each year.
Contracting pays so well, and traveling in the 3rd world is so cheap that there's just no way you can burn through your savings before boredom sets in and you need to work again for the mental challenge.
Catastrophic coverage health care is $100/month if you're young and healthy. Travel Medical is on the order of $500/year to get you airlifted home when you get shot in the Congo. Those in combination will keep you alive for the duration.