Over the two decades I've enjoyed living here, I've discovered an lot of the unusual, offbeat, fun and sometimes surprisingly marvelous places that don't make all the tour guides. All within an hour or at most two, they provide an interesting alternative to Disney World or Busch Gardens and a taste of old Florida.
The Don Cesar on St. Pete Beach and The Vinoy in St. Petersburg are wonderfully restored Art Deco Hotels where it's wonderful to hang out in the lobby or lounge, drink martinis and listen to the Cole Porter tunes on a baby grand or a jazz combo.
The Lakeside Inn, in Mt. Dora is a bit of a drive but pleasant if you take the back roads. What awaits is the oldest frame hotel (some of the plumbing too) in Florida on Lake Dora. Big old front porch with rocking chairs, a homemade apple pie to take home with the weekend special. Antique shops, boutiques, restaurants, sunset boat rides are all within walking distance. Make reservations well in advance for the lakeview rooms.
My girlfriend's father Pete, likes the Sarasota Kennel Club for the dogs and off track betting on the ponies. They just opened a "Texas Hold'em" card room that I won't venture into. But the best kept secret is the food, I had a Delmonico Streak there as good as any that weighed more than a pound for $14.95 plus bad wagers.
The Shell Factory (and museum, really) in North Fort Myers is a real classic and fun for the kids. Acres of Sea Shells, Carved Coconut Heads and every Florida souvenir known to man and a Tableau of Stuffed African Game Animals with a bar offering cold beer and wine.
Boca Grande is worth the 45 minute drive south along Lemon Bay to a timeless sense of refined island living similar to Mackinaw Island on the upper peninsula in Michigan. The Gasparilla Inn, a premier destination on Florida's pristine Gulf Coast since 1913, is pretty exclusive. Great fishing charters there and it is the Tarpon Fishing Capitol of the World. A couple of buddys and I got there for a charter canceled due to weather about 15 years ago and had breakfast at Dolphin Cove Café, Paul Newman and Joann Woodward were at the next table.
A good reason to have a boat or rent one at is to cross Charlotte Harbor and dock at Cabbage Key, a resort of sorts, accessible only from the water.
Some others for fun:
Warm Mineral Springs, A Roadside Attraction since 30,000 BC. The "Original Fountain of Youth"
Salvador Dali Museum Hello Dali.
Alligator Wresting, Swamp Tours, Myakka State Park, Edison Museum and the list goes on.