Technomading?
kareemm: I am living this life right now.  Lived (mostly) in Vancouver and Buenos Aires last year (with 1 month stops in LA, NY, and Toronto, and purely fun travel to Antarctica, Ireland and South Africa).In 09 I've been to India (vacation), London (worked), Vancouver (worked), and I'm currently in Italy (both vaca + work).  Heading to Budapest in two days to rent a place for 3m.The most common question I've gotten is how to fund this.  I've funded this with consulting gigs and living in cheap-ish places - living in Buenos Aires, for example, is a great way to bootstrap a startup.  Building a more scalable biz to do this - consulting is a fine way to make a living, but a terrible way to build wealth.It's great to see the world and get a better sense of the nuances of a culture than a hit-and-run trip.  But it's not without its challenges.  Off the top of my head, here are three:- the biggest (for me) being balancing the desire to explore a new city with work- A close runner up (believe it or not) is finding good broadband- Building a community where you move to is often tough, though meeting people through couchsurfing.com has been awesomeIf you have specific questions, please fire away here.  I'm also going to teach a free class on www.edufire.com about this soon and I'll drop you an email about it if you email me directly (blog at reemer dot com).There's more about how to live the technomad life in this interview I did:
http://mixergy.com/business-nomad/And on my blog (too busy bootstrapping to update since Feb, but some info there):
http://howsthewifi.comEDIT: An afterthought - whatever you do, don't let someone else tell you it's not possible or there's a better way to do it.  Figure it what you want, then explore your options yourself (learning from people who've done it).The benefits of living like this will do two things - build your self-awareness and build your confidence in yourself.  It's close to the best way I've found to take responsibility for my life - I'm eating what I kill and living in cities where I know nobody and don't speak the language.  You'll learn a hell of a lot about what you're capable of and that's the best damn part imho.