Places in the US with really good weather are expensive, film at 11 ...
I like the idea of traveling around and pondering what you think about this or that place for retirement. One small city I like is Greenville, SC. We visit there on occasion. One can potentially live NEARish a place one likes and travel there when the mood strikes. That's why Nevada was on my radar for a bit, no state income taxes, some nice areas, near CA.