I copied the discussion below from the American Great Loop Cruisers Association (an orginization this writer HIGHLY recommends for those undertaking the “Great Loop”). There is some very good advice here about what it’s like weather-wise to cruise the Carolinas and Georgia coastlines in late fall.

Hello All,
John and I hope to begin heading South… for the very first time… from NJ beginning early- to mid- October. We are planning to have some work done on our boat in the Chesapeake. Currently, we are
working on our calendar. If we are delayed and cannot leave the Chesapeake until mid- to late- November… or even early December, how is it traveling through the Carolinas and Georgia at that time?
Your knowledge and experience sharing is appreciated!
Sincerely,
Paulette and John

Nov and Dec can sometimes be a little nasty but there are ample good days — just do not get in a hurry or committ to a time table that tempts you to move when you would be better served sitting–occasionally for up to a week or so. There are several big sounds that can be miserable to dangerous if run at the wrong time. The predominant winds at that time are N to NE so that helps. There are some good stops and nice anchorages and typically no bugs—a BIG plus.
Howard

Cold with more than a few below freezing nights(heater?) but generally warming up in the day all the way to south Georgia, no crowds in popular anchorages or marinas, northerly gales frequent in the fall to late fall so mostly you can only travel in between to cross all the big water, very short days (8 hrs daylight) some closures of marinas and stores in vacation centric locations. But No bugs! 🙂 so enjoy.
Joe

John and Paulette,
In addition to the other advice you’ve had:
We’ve run the ICW from the Chesapeake to the West Coast of Florida for several years. The boat is a slow trawler, and makes about 7.3kts (8.4 mph). We average 22 actual travel days, and around 28 total days, for the trip. We like to hole up in Belhaven, NC, and Charleston, SC, for provisioning and laundry. You will not have seriously cold weather until January below he Chesapeake. Chilly mornings and evenings, yes, but not hard freezes. Because the water is still warm, your reverse cycle heat pump should do fine. We do not run the generator overnight, so we carry a quilt for the cooler nights, which works fine.
There was an earlier comment about space in anchorages. You need to watch that. The various insurance companies have exclusions that
specify where people can be on certain dates. In the last couple of years, we have found that people gather up in Norfolk on November 1st
and again on November 15th. So right around those dates, some anchorages may fill up. There is a second line at Cape Hattaras for some insurance companies, including ours, and a third line at 32 N (about Savannah) for others. In general, this won’t be a problem if you are a day or two off one way or the other.
Places to be very mindful of the weather include offshore New Jersye (of course), the Delaware and Chesapeake Bays (you knew that), Albemarle and Pamlico Sounds, and the sounds and open stretches in South Carolina and Georgia (Port Royal, Calibogue, St. Andrews, St. Catherines, Sapelo, etc). These are exposed areas that can be rough and unpleasant. Some can be downright dangerous in the wind is up. We find 15kts of wind and 2′ seas is about the planning limit where we feel comfortable.
Places to consider for Thanksgiving include Brunswick and St. Marys, GA. Both have large pot-luck gatherings for cruisers.
Our experience has been that Fall usually offers up more docile weather than spring. Of course, major late season atlantic storms can be an exception, so be very alert to the weather developing in the Caribbean and Atlantic Basin. Otherwise, tho, in the fall, t’storms are unusual; not so in spring. In late October and November, you won’t have bugs. In spring, by May, watch out for Green Heads in GA and the Carolinas, all the way north through New Jersey. They swarm during the warm days, and can make life quite unpleasant for the unwary.
Peg and Jim Healy aboard Sanctuary,

I lived in Charleston for 5 years. I remember one Christmas Day going to the beach and sunbathing as if in July. But from December on – and more so Jan Feb abd March it can be bitter cold with strong breezes to add to the chill. Of course much the same situation applies to Georgia and North Florida. Which is why of course `snowbirds’ tend to go on to South Florida and the Abacos / Exumas. But I remember too a holiday pretty much ruined in the Abacos by cold cold weather in mid Feb. Believe me – there ain’t much to do on a desert island when it’s cold. The magic formula we all try to use is to leave Chesapeake mid October at the earliest and then edge south trying to both offset cold blustery weather while avoiding hurricanes. The latter of course is pretty much essential – even if it means turning round and fleeing north. You don’t mess with hurricanes. If you do get unavoidably trapped in the path of one then do your best to secure and batten down your boat – but get the heck off it and seek refuge ashore. Better to lose your boat than lose your life’¦’¦. Have a wonderful trip – I’m sure you’ll enjoy every day of it. Right now I’m tied to a free dock in Portsmouth – but too much rain these past few days has resulted in water over the dock so I have to slosh ashore in rubber boots! But hey I tell myself – this is fun isn’t it?
Arnold