What are normally considered winter months are all "snowbird season" here and motel/hotel rates tend to be higher. (traffic is a lot heavier too)
If you are going to bring the family as in family vacation you might want to consider one on one of the nearby beaches to keep the rest of the group happy.
If you want to run with us, schedule it so you are here on the 2nd or 4th Sunday of the month as those are the official club run days. Both Chris and myself are pretty good about trying to accomodate an out of towner that happens to be here on an off weekend but for the club effect ,the 2nd and 4th Sunday's of each month have the bigger gatherings of boaters/racers.
(my email is there as well, hidden on the bottom of the page as webmaster contact. I can PM you my phone number, too)
I try to keep the planned schedule posted here.