From the ocean to the lake or vice versa. This is what the Ocean-to-Lake Trail is promising. It starts at the gigantic Lake Okeechobee and leads you to a wilderness, you would not expect in populous Florida. After 100 km it ends at Hobe Sound Beach at the Atlantic Ocean.
The main hiking season, if there even is one in Florida, starts in January. Mid May it might be too hot to hike the swamps. I startet my thru-hike during Spring Break anyway, when everybody else is celebrating. Wet feet, alligators, a bobcat and (un)planned fire where just some companions. Enjoy watching.