If you do the numbers I bet you will find that a week to 10 day charter is cheaper.
Do you really want your boat going to Florida with inexperienced crew and not you. You seem to be as anal about maintenance on your boat as I am. How much is it going to cost you to have someone maintain it in Florida or elsewhere and are they going to do it to your standards? If not, how are you going to like working on the boat for 3 days while the family watches and wonders if you are leaving?
Winterize the tanks and keep sailing.