for what it is worth, I did it once from Norfolk in December. I went down the ICW to Beaufort very carefully (my draft is 6'4") stopping along the way in various marinas. (Bring an electric heater to plug in.) Since you have very short days, you need to plan carefully remembering that given your draft, your anchoring options are quite limited. Also, my rule was if it is sleeting, I wait another day. Taking your old ski outfit to wear under your foulies helps. But once at Beaufort the weather was more temperate, and I made Fernandina my next stop. Then down to Palm Beach and then over to the Abacos or to Ft. Lauderdale and/or Miami and off to the Exumas. The good part is that you will be alone on the ICW. There was a day where I saw only one other boat. Also the marinas are largely empty as well. But the warm Florida sun feels even better after your chilly beginning. So don't let the chill in the air stop you. Life has a way of conspiring against us and I for one regret the times when I said I'd take a sailing trip next year. Sometimes that next year never comes.