Graden, I've never actually sailed in the keys but it is probably a nice place to spend the winter. There are mooring
fields all around FL now, best I can tell they are around $300 a month, maybe $250 and includes pump out, dinghy
docks, showers. Dinner Plate Key is one IIRC
Fernandina has one such mooring
field, and is close to Cumberland Island, somewhere I like to spend time. I would grab the cruising guides
and start heading south if you've the freedom to do so. Forget the trailer and go across the Okeechobee waterway (after checking water
levels, which I presume are fine now) and cruise
the west coast
of FL. I bought my boat there and sailed her home to NC, but thought it would be a nice place in the winter. MAybe by the end of the winter you'll be feeling confident and you can have a little gulf stream
I think municipalities are starting to tax more now, so watch out for taxes
if you stay put somewhere for a while.
You might get some really nice weather
this year, never know. It has been in the 60's here in the mountains of NC so it must have been nice in coastal SC. Get ready for a winter camping experience and head south. I don't know what that nimble draws, but I'd sure anchor
back in Cape Romain and harvest some oysters when you start your journey.
Unless you're feeling pretty rugged, or have a good heat source on the boat, you're going to want to tie up and plug
in a little heater. I have a "heater buddy" on my boat, and don't tie up or plug
in, it just costs too much.
even the heater buddy is expensive to run, with the gas canisters. Shouldn't have to worry too much about all that several degrees south in latitude.