By the time your visa is due, you will have quite pleasant weather. It would be a heck of a shame to be sailing in Florida and not get across to the Bahamas. It's only a stone's throw away and the sailing is very good. Crystal clear water, great beaches, decent people and you can fly from fort Lauderdale or West Palm to Marsh Harbour for almost nothing if you do a little searching. I have sailed Southern Florida and the Bahamas but have yet to get into the Gulf.
Hopefully someone will have good information for you. Have a look at The Cruising Wiki (top of this page) and also look at Noonsite.com. Loads of good info on the Gulf and across to Panama.
I just left south Florida two days ago and am now up around Kentucky for a bit. If I get back to Fort Lauderdale/Miami in the next three months (which is well on the cards) I'll send a PM and say g'day
"if at first you don't succeed....Redefine success"!