Not enough time... (In my opinion) If you start setting "drop dead dates" things go south in a hurry. Iffy weather
, boat problems, etc get lost
in the drive to "get there"
Quick look at the numbers...
Sandy Hook to Charleston straight down the outside, (Not a trip for newbies or the faint of heart) around 600nm or (using my offshore rule
of thumb of 100nm/24 hrs) 6 days of 24 hr sailing. 2 to 4 days when you get there to recover, and fix broke stuff.
Outside from Sandy Hook to Norfolk 275nm (or there abouts) figure 3 24hr days. Norfolk to Charleston in the "Ditch" 750m. Ditch days = 50m on average, no night sailing, tides etc. 750/50 = 15 days. Total Sandy Hook to Chucktown 18 days.
You might save some time jumping outside at Cape Fear, and running down to Charleston, but still a couple of 24hr days.
Allot more time, or wait till you have more time.
I'm just sayin'...
Myself, leaving out of middle Chesapeake in a couple weeks, plan to stop in Savannah to visit friends. When they ask when I will arrive, my answer is "When I get there". No earlier than the end of the first week of Nov, if the weather
is perfect, nothing breaks, and I don't get distracted along the way....