Ashland, OR - Great climate. More culture and better restaurants than you'd expect to find in a town of that size. Not sure where the nearest International airport is.
Flagstaff, AZ - College town, mountains and forests, but a short drive to the desert. Possibly too snowy for me in the winter. Nearest big airport is probably in Phoenix.
Central Texas Hill Country, due West, Southwest or Northwest of Austin (San Marcos, Marble Falls, Fredricksburg, Burnet) - This is a pretty big area and there are a number of towns that vary in attractions and attractiveness. Beautiful landscape, rivers and lakes, but it is pretty hot, particularly in summer months. Austin and San Antonio nearby though.
Southwest Florida had been on my personal list (yeah, it's Florida, but it has a lot going for it), but after these most recent hurricanes, I don't think I want to deal with that mess.