Hi Jeffrey,
...depending on how much time you decide to dawdle through the Chesapeake, or perhaps the NC sounds... Once you get south of Hatteras, I wouldn't worry too much about the weather in February. It's been so variable over recent years anyway, any such prediction is pretty tough to make. This year I didn't leave NJ until New Year's, and although I had a few chilly days at the start, I still think the coldest night of the entire trip was probably about 10 days later, while passing by Jacksonville... So, you never know, but if it turns out to be a winter where fronts are coming thru regularly, you might get freezing weather all the way south of Canaveral...
Dan's recommendation of Brunswick is a good one, especially if your insurance keeps you out of Florida before November... If you don't make it that far down, another good option is the Myrtle Beach area, plenty of options there... There are several big condo/resort developments that I've heard offer longer-term transient dockage at very reasonable rates, better than you're likely to find at the regular ICW marinas that cater to snowbirds... I've also heard nice things about Osprey Marina, fairly convenient to the Myrtle Beach airport... That's a consideration and an advantage of the MB area, Spirit flies from NJ to MB, it would be one of the easier and more affordable places to leave and return to the boat from...
Enjoy, it's a great trip... Suggest you budget a bit of time to meander thru the NC sounds, Cape Lookout, etc - that's one of my favorite parts of the trip...
best regards,
Jon