If it weren't for the surfing, I'd suggest Asheville. How would he like white water kayaking and rafting instead??
I'm currently in a similar quest. I've always wanted to live in Europe. I lived there once for a few months, but circumstances were different, and it did not work out. Now, however, I think I could do it. Paris, Dublin, Bordeaux, and some smaller cities in western France come to mind for me. I'm fortunate in that I am an EU citizen, so that really cuts down on the hassle.
My criteria are near the sea, access to a city, good cycling, fresh markets (European markets or farmers markets), and as few shopping centers, cul-de-sacs, and SUVs as possible. Oh, and good gardening climate.



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