FL Panhandle to Tarpon Springs
I have made the crossing several times. The shortest route would be from Carabelle/Dog Island to Tarpon Springs/Anclote Key. It is an overnight trip that took us about 24 hrs. I have also gone from Government cut at Applacicloa to Anclote key about 24 hr+. The last couple of times we went from Panama City to Clearwater and that took us around 36 hrs. We did motorsail on all these trips.
Once to Anclote Key, you can stay inside all the way to Ft Myers or you can hop in and out: Clearwater, Johns Pass, Pass a grill, Tampa Bay (Egmont Key channel and SW passage), Longboat, Sarasota (new pass and Big Sarasota pass ,both with local knowledge), Venice, Boca Grande, Redfish pass, San Carlos/ Sanibel, Naples, Marco, Shark River and then the Keyes.
Anyway a great sailing/cruising area.