Florida Fan
My wife and I moved here about 1970 from up nawth for the same reason. We wanted more sailing less snow shoveling.
We've lived in Tallahassee, Largo (St Pete), Cocoa Beach, Lakeland and a few other spots. All have great sailing of one kind or another you just need to be flexible about what kind of sailing you want.
What I mean is that the central west coast (Tampa-St Pete) is great sailing from one design dinghies to ocean racers and every kind of cruiser you can imagine. While areas like Lakeland are more suited to lake sailing or day sailing in small one designs. We used to race Windmill class sloops in Lakeland.
If you like racing, the main racing seasons here are fall (Sept - Dec) and spring (Jan-May). Davis Island YC, Tampa YC, St Pete YC, Clearwater YC, Bradenton YC, Sarasota Sailing Squadron, Tampa Sailing Squadron, Venice YC, Etc. Etc ... many great clubs, host events of all kinds. We're leaving on Tuesday for the Clearwater-Key West race aboard a friend's boat. We'll be back in a week or so. Some clubs are fancy with expensive dues and tennis courts while others are more laid back and focused on sailing, You just have to choose.
Cruising here is fabulous if that's your interest. The Gulf Coast has an ICW that runs from Tarpon Springs to Naples with inlets at least every 10 miles or so. That means that if you cruise coastally you're never far from protected water. The water near shore tends to be shallow however and a few inlets can't be negotiated in boats drawing more than say 3 feet. Marke inlets can generally handle almost any draft although the ICW itself can be a challenge for anything over 6 feet. BUT the gunk holing possibilities are endless especially for shallow draft vessels.
On the East coast the ICW runs the entire length of Florida. Inlets there tend to be bigger and deeper but also somewhat farther apart. Some areas of the ICW can be shallow but you wouldn't believe the cruiser migrations that happen twice a year as all kinds of cruising boats travel from the Chesapeake and points north to the Bahamas and Caribbean.
Every waterfront town along the east coast has a yacht club or sailing club of some description. The shallow lagoon system behind Cocoa Beach for example, has a very active multihull group. Farther south, in Miami or Ft Lauderdale the yacht clubs tend to the elegant but many host regattas for all types of sailboats. Plus the Keys and Bahamas are a day's sail away.
In addition, most of the larger towns have community sailing centers. I worked at the one in Clearwater where we rented small sailboats, taught sailing, hosted major regattas (like the Laser Midwinters), organized charter trips to the Caribbean, ran summer camps for kids, etc.
If you want sailing in Florida you can find it. We live in the center of the state and right now but we have our boat at New Port Richey, just north of Tarpon Springs, an hour and a half away. That's only because we're now retired and the living is cheaper over here but we still want to cruise our E38. BUT no matter where you live you're not far from great sailing.
In this day and age, I'd go where the job is, then study the local sailing scene and see what appeals to you. You won't have to go far to find what you want.
As far as finding what you want, get a copy of Southwinds magazine (free at Florida West Marine stores and other places) or their website
http://www.southwindssailing.com/ and subscribe. It has the contact info for 98% of the sailing/yacht clubs in Florida and some mediocre articles written mainly by stiffs like me.
TAN ON!
... and I can use that term as I am originally from GA and have some in my family!).
