Where is the world it is pleasantly warm, but not hot at least 8-9 mo/year?
A sea and or a lake is required, preferably english speaking (at least in a large part) populace.
I cannot think of anywhere apart from few small places in The Caribbean, with a threat of hurricanes, etc.
I've been through several hurricanes already, it's a thing to avoid if possible.
Without considering language, I was also thinking about Greece (including Corfu), some Mediterranean islands (Crete, etc.), maybe Canary islands.
Maybe I should learn Spanish or Portuguese, finally.
Suggestions?
Hawaii. Side of the volcano, pick your elevation and you can pick your climate. Then a few minutes to either the summit and wearing a winter jacket, or to the beach and wearing nearly nothing. Of course there's that little issue of cost of living.