My current plan is to live in the great cities of the world, 3 months at a time. Since 3 months is what you can usually get for a visa. So far I stayed in London which was fantastic, for 5 months, and have been in Paris for 4 months, which has been great for learning french and getting lots of work done.
Last year I was just working in my home city, doing the same sort of stuff. This year has been a lot more exciting, met great people, and worked with some exciting startups in London. Fantastic.
I should have added something about the Visa situation. If you have a parent or grandparent born in a European country, take your birth certificate with you and try and get local citizenship along with a passport. Almost everybody I had met while travelling had done this.
Check the websites for the various consulates, embassies and travel advice from your home country to find out what you can and can't do. Also remember that in many second and third world countries the written rules and the real rules are two different things - this is how I came to get a third passport in Serbia for $10 which I used to get into Hungary (legally, this time) in the summer season.
There are also special type of visa, for eg. with an Australian passport you can easily (meaning, just an application) get a 2 year working holiday visa in the UK
For everywhere else where you have Visa waivers, what I would do is use it as an excuse to get away to another country and come back in. I did this in order to stay in South Africa for 2+ years. Never had any problems getting the visa renewed each time.
It all depends on which passport you carry. I am fortunate enough to have an Australian passport, but there are other western passports that are good with Visa issues.
Flights in Europe and Asia are very cheap, lots of established low cost carriers.
The other tip is that even in the most expensive cities in the world you can find shared accommodation with enough space for a bed, desk and internet connection for a few hundred dollars a week. Just ask around. That type of accommodation is usually clustered around suburbs, for eg. Acton and Shepherds Bush in London.
I really should do what Alex has done here and write some blog posts with tips and experiences.
>It all depends on which passport you carry. I am fortunate enough to have an Australian passport, but there are other western passports that are good with Visa issues.
I'm pretty sure there are a bunch of special advantages to having a Commonwealth passport in a Commonwealth country but I can't remember any off the top of my head.
Last year I was just working in my home city, doing the same sort of stuff. This year has been a lot more exciting, met great people, and worked with some exciting startups in London. Fantastic.