Tampa St. Pete is best for LOCAL sailing and plenty of interesting places to go. Draft is an issue so the right boat is necessary in your size range. Lots of good sailing support places.
Miami is poor for local sailing....but both the Keys and the Bahamas are great destinations for vacations. Excellent sailing support facilities in Mia & Ft. Lauderdale.
Charleston as a sailing venue has very little to recommend it other than being a truly great PLACE.
I'm sure others will kick in...but those are my opinions. You're already in the best place for local cruising between the outerbanks and the Chessie!
A lot depends on the time you will have. I'd go Florida East coast if I had the time to enjoy the Bahamas and Keys...otherwise Tampa.
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