First of all, I would avoid I-95 altogether AT ALL COSTS. I cannot stress this highly enough. You DO NOT want to pull a large trailer through the likes of Boston, New York City, Philadelphia, New Jersey, Baltimore, Washington DC, etc, etc, etc. Take a more westerly route, such as I-81, down through the Appalachians. Trust me. That said, welcome to Florida!! We live in the Ocala area, somewhat north of where you will be, but we often trailer our Catalina 22 down that way. We love the Gulf coast. It is all very beautiful from Tampa all the way down to Marco Island, miles and miles and miles of beaches as far as you can see. Charlotte Harbor is nice, featuring the islands of Sanibel, Captiva, and Cayo Costa. Further south, beyond Marco Island, is what they call the 10,000 Islands, which we enjoy very much. It is the western boundary of the Everglades national park, which is the largest wilderness area east of the Mississippi River. From there, you can continue south to the Florida Keys if you like.The water is very shallow (as is the case for almost all of western Florida) so have a good depth finder, and don't put 100% trust in any chart where the sand is shoaling. If you wish to sail north to the Florida Panhandle, there is GREAT sailing from the tiny town of Carrabelle all the way to the Alabama border (and beyond). Hope this helps. And again, welcome to Florida!