Here is an option which will give you plenty of nice cruising and save a pile of money and worry this winter.
Head north on the ICW make it as far as Lake Michigan for the winter layup. Most marinas on Lake Michigan are way cheaper than East Coast, safer, conscientious and a shorter flight back home. Shop rates are around $100 an hour compared to maybe twice that in the big East coast cities.
I can make some recommendations if you are interested.
pete
Curious about bringing a FL boat north for the winter and if heated storage is suggested. I would think that any water intrusion into the core would freeze and split the fiberglass and surrounding structure. A good moisture meter survey might find most of it, but still an expensive way to find that some was missed. Isn't heated storage expensive?