Spring (Mar to May): kingfish run nearshore, tarpon show up in the passes, grouper offshore. The best overall stretch.
Summer (Jun to Aug): red snapper season offshore (dates change yearly, check FWC), tarpon in the passes, snook on the beach at dawn. Go early, storms come in the afternoon.
Fall (Sep to Nov): the second kingfish run, redfish schooling on the flats, flat calm days offshore in October. Stone crab season opens October 15: five traps per person, claws only, a free FWC trap registration plus your license. The Old Salt King of the Beach kingfish tournament runs out of Madeira Beach in mid-November, and the Saturday weigh-in at ROC Park is best watched from a boat.
Winter (Dec to Feb): sheepshead on every piling, trout on the deeper flats, grouper nearshore between fronts.
Red snapper: the Gulf season for private boats changes every year. FWC has been adding fall weekends and holiday windows lately. Check the current dates before you plan a trip around it.
Licenses: anyone 16 or older fishing from a boat needs a Florida saltwater license, which you can buy online in a few minutes. Charters cover you.