Originally Posted by Icycle
I'm surprised no one has mentioned New York City. If you can afford it, and you like the big city life style, New York is a great car-free city. In Manhatten, being car-free is normal. There is excellent public transportation. Shopping and services are are often within walking distance, and if not, you can probably get there easily by subway, bus, or taxi. There is even a growing culture of transportational cyclists.
What about San Fransisco? Isn't that also a compact, dense and expensive city with great public transit? Of course I'd hate to ride up (or even down) those hills every day after work!