Welcome aboard. It didn't take me long to start enjoying the trip instead of the destination! I'm sure you will be the same. Show us some pictures when you can.
Yes the 37 Hershine is currently in Palmeto, FL The plan is to start Osprey's 2nd and my first loop by heading south this week. Shooting to be in Key Largo by, maybe, sometime, around, the the last week of March. I have heard great things about SW Florida and am not in a rush. It's 19* and getting colder on Cape Cod tonight.
You'll find some great cruising grounds from Palmetto south especially between there and the south tip of Sanibel. If you have time a trip up to Ft Myers might be interesting.
Bon Voyage
Lots of nice cruising around the barrier islands North of Fort Myers. Pelican Bay on the NE end of Cayo Costa island off of Charlotte Harbor is one of my favorite spots to escape to. Very protected anchorage to watch nature from.