Short winters and cool summers (cities, towns, year)
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San Francisco. Seattle and Portland are also options, though they have warm summers. Thing is, for most of the year the weather is cool and rainy. And summer, while sunny, usually only tops out in the 80sF at highest, maybe some hotter days. Either way, it is a dry heat and that means cool nights even in summer, and the cool ocean breeze keeps one from getting too hot.
I forgot to mention snow. I like snow. Just not for 6 months. I am starting to consider the smaller ski towns.
Then Big Bear, California. But it's not a city, it's a small mountain ski town just NE of the Los Angeles Basin. Summers are reasonably cool and while it gets some snow in winter, it's not 6 months of snow and cold.
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