While I do not disagree with many of Sal's sentiments about Florida with respect to the southeast coast, perhaps from Palm Beach to south Miami, the situation on the southwest coast, focused around the south Tampa Bay area, is quite a different matter. We have lived in this area since 1993, although I did commute to my office in Santa Barbara bi-weekly until mid-2008, and have found it quite delightful. Previously, we lived and sailed on the west coast, from as far north as Orcas Island to as far south as Manzanillo, and have found the sailing here no less enjoyable. While the terrain is certainly not quite so scenic, the mere fact that one can swim or wind-surf without a wetsuit makes the area our favorite, hands down. As for heat/humidity during the summer months, while it can be oppressive for a few weeks each year, we have found it to be far cooler and more moderate than other areas of the Country during the summer including the Milwaukee-Chicago area, New York/New Jersey, Washington and the north mid-Chesapeake. Friends and relatives from these locales that often visited us during the summer months, while their children were out of school, often commented on how much more endurable the conditions where here than at "home". (The key is proper dress and decent shade from the direct sun.)
While there is a threat of hurricanes (the season here is really from mid-August through mid-October), because of the arrangement of the coast, prevailing wind/weather patterns and currents in the Gulf during the "season", the southwest coast is far less at risk than are other areas such as the north Gulf Coast or the southeast coast of the state. That is not to say we haven't had storms, and we prepare for the worst whenever we are threatened, but we have never suffered anything worse than wind-blown foliage and some chafed lines as we are tucked into a protected corner on a river several miles off the south Bay and there are plenty of protected coves and bayous where one can anchor-out (with proper ground tackle) if necessary. Actually, by comparison, we suffered far, far worse damage/injury from earthquakes while living in California, which can strike at any time with no forewarning.
A further major advantage of this area is the relatively low taxes and cost of living, state and local governments that are not "out of control" and so are largely unintrusive and a largely amiable and welcoming population. (My daughter once commented after a trip to NY to spend time with her cousins one summer, that "everyone always seemed so hostile". We told her to be glad we lived here to which she responded "I really am!")
Lastly to the sailing--whether day tripping, near-by cruising or longer distance cruising. For a better sense of that, take a look at the charts available on ActiveCaptain.com. While the water can be a bit thin in some areas, we draw 6-1/2 feet and it has not been much of a problem. And, we can reach virtually anywhere one might want to cruise along this coast in little more than 30 hours, tops, (and when we arrive will not be forced to line up on fore-n-aft moorings packed together like Sardines, a-la-Catalina.)
N'any case, my contribution for the day, FWIW...