Since you can stay in the ICW
from VA south the waters are protected so you will not need to be quite as concerned about stormy weather
. I have known people to head
south throughout the winter. Just gets colder, more chance of rain (or sleet and snow if you are still north of GA).
As long as you stay in the ditch I don't see time of year as a restriction. Just watch the weather
and if it's blowing a strong Nor'easter you may want to stay put in a good anchorage or protected marina until the wind
Do you have a heater? Thermal underwear?