You can do it all winter but some weather delays could be measured in weeks instead of days.
Finding fuel isn't all that hard, but water and electric at many places north of North Carolina may be shut off.
I have left as late as Dec 15th in a 6 knot boat and it wasn't too bad.
By January, it almost becomes a survival trip till south of Hatteras.
I wouldn't do it unless the boat was a pretty special craft, outfitted to the teeth....and I endured USCG icebreaker duty.
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