I was having a chat with one of my best friends who had moved to Sarasota about 15 years ago. He mentioned that there is a very active/organized gay retiree community there. The west coast of Florida is a bit more reserved than the eastern coast (think midwestern vs. New York), which would include Wilton/Ft. Lauderdale, which also has a substantial older gay community. The real estate bust hit south Florida pretty hard so there are probably some bargains to be had, property-wise.

Some of my older friends have moved to San Diego and have been thrilled with it, not only for the climate, but that they "fit in" better than in some locales.