Mexico Beach, Florida
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"A quaint little drinking village with a fishing problem" is the motto of this panhandle town 110 miles from Tallahasee named for the gulf that unfurls to the south. Mexico Beach is very much like the version of Mexico described in country songs: No shirt, no shoes, no problem fitting in. The small downtown area is perpetually full of locals chatting about their latest catch. 

What to Do for Fun: Captain J.R. Riley cruises offshore for red snapper, grouper, and amberjack. A sandside deck called Tou-Can's is the social headquarters, serving up raw oysters, rum drinks, and knockout views across the Gulf. The Driftwood Inn has rooms overlooking the surf.