I can't claim one best location, but I can narrow your search. One thing that is apparent when comparing when comparing "sailing communities" of Florida to those in New England & the Chesapeake is that in Florida, with year round sailing, you won't find as many seasonal summer sailing camps and schools. Another interest in Florida sailing is to notice that many locations that have a large number of sailboats are locations without nearby protected sailing areas. Places such as Fernandina, St. Augustine, Daytona, Vero Beach, West Palm Beach, and Fort Lauderdale have large numbers of moored and docked cruising sailboats, but they have only offshore or small strong current sounds or bays for limited sailing. The best sailing locations are those with offshore access as well as large protected inland areas without harsh currents and they are the following (in no special order):
1- The St. Johns River - south of Jacksonville, thirty miles from a class A-1 inlet, search North Florida Cruising Club, less than the average state real estate costs
2- Indian River- from near Titusville to Melbourne with more open sailing south of Cocoa with an excellent inlet at Port Canaveral and a fairly good inlet at St. Lucie.
3- Stuart- up the St. Lucie River from the St. Lucie Inlet, look at the area west of the Roosevelt Bridge, some interesting waterfront properties at Kitchning Cove.
4- Biscayne Bay- One of the largest sailing communities center around Coconut Grove and arguably the best location for sailing, quick ocean access and close to the Bahamas
5- Buttonwood Sound- bayside of Key Largo, Key Largo sailing club (a Nonsuch center) best suited for drafts 5' or less.
6- Marathon, Fat Deer & Boot Key- open to Hawk's Channel and Bayside through 65' fixed bridge. Huge liveaboard mooring field
7- Key West- Much to offer like Marathon, but note #5,6 & 7 offer little hurricane protection options
8- Fort Myers Beach- though Pine Island Sound is mostly too shallow there's easy access for sailing inside point Ybel and waterfront up to Fort Myers under 55' fixed bridge.
9- Tampa Bay- large sailing area with excellent Gulf access. Check Bradenton Regatta Point & Twin Dolphin Marinas as well as Gulfport, much more in Tampa & St. Petersburg.
10- Panama City, Destin, Ft. Walton Beach and Pensacola are likely possibilities too, but these have not been within my frequent cruising area. Take care and joy, Aythya crew