I do like southwest Florida and Ft. Myers Beach excels; however, there is not a greater need for confidence to cruise on the East Coast. Four areas along Florida'a east coast allow for casual protected sailing as well as ocean access. From north to south these are: The St. Johns River south of Jacksonville; The Indian River from Titusville to Melborne; The St. Lucie River at Stuart; and Biscayne Bay south from Miami to the upper Keys. Fort Lauderdale is a wonderful boating community, but no sailing except offshore. The St. Johns River has the best hurricane protection (my opinion); Titusville has the best storage on the hard (Westland); Stuart has the best mooring field; and Biscayne Bay has the most protected sailing area and Bahama access.
'seems to me that you would do better with headroom at 28'-30'...'lots of good deals about!
.....and an emphatic NO! Those of us in Florida are not wondering why cruisers would want to be somewhere else than Alaska; however, beware, most of us here are well adapted to the heat and humidity. Take care and joy, Aythya crew