Gosh, this thread has really made me start thinking about the unthinkable. I really do have to start planning more.

I just got back from Fort Myers, FL yesterday and it seems like there were so many people on bikes both old and young. Interestingly, many don't seem to be concerned with wearing helmets. I did notice there were some elderly people who were on tri-cycles complete with panniers and flags who had been shopping somewhere. I thought that it was such a neat option to continue getting around in the absence of public transport.

I think NYC is great for it's transit system, but generally unsafe and cold.
Miami sounds nice and warm,not sure about affordability. The Golden Girls sure made it look like fun though.