A broader Florida recommendation...
Tony, I like reading the replies you've received so far because in part they reflect the various 'positives' you'll find around the State. And that's my first point: Florida is diverse and offers multiple sailing venues, but few of them are disappointing. Which leads to my second point: skip the sailing issue initially and look at the communities, regional cultures (there are multiple distinct 'personalities' within this one state), what's offered in each area as it relates to your non-sailing interests & needs, and then choose wisely. Charlotte Harbor's large bay is mostly protected inperpetuity as the state bought up the wetlands so they couldn't be developed (good for them/us!)...but if you enjoy a bit of 21st century civilization, good theater, a nearby large university, etc., Port Charlotte and Punta Gorda is not where you're going to find them. We sailed into Tampa Bay 13 years ago from the Caribbean and couldn't leave; it offers everything to us that we were & are looking for. But with 2 million folks in the 3 counties, it's a Big City. If that's a dissuader, who cares about the sailing?I'd recommend you treat yourself to a car tour, taking in at least five of the key distinct parts of Florida where sailing is frequently enjoyed: The Pensacola-Destin area of the Panhandle, the Tampa Bay area, the Sarasota-Venice-Ft. Myers stretch (all small communities with their own distinct personalities), the West Palm-Ft. Lauderdale region, the Indian River 'inland+coastal' area perhaps centered around Port Canaveral, and the NE Florida/Jax area and adjacent St. Johns River. Each of these locales is distinct, and each offers their own treasures as well as gripes.Jack