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There's a lot of cool places in FL. Too far south and it's too hot, but somewhere along the northern east coast is nice. Last time I was in Jacksonville I was impressed. Not really a beach town, but close enough to the beach you can enjoy without sand everywhere.
If you do like the beach, the southern coast of AL is very nice.
Me personally, it would be New Orleans. It just fits me, but it's not for everyone, and my wife would never want to live there.
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