Duke and Seadaddler
As others have said you won't be able to do alot of sailing except across the sounds in NC. But, you can motorsail whenever you're not in a canal and the winds are ok.I've been making the trip each year for the past 6 years.October is the nicest month. Still warm, still ok daylight hours, but past prime Hurricane season.From NY, wait for a weather window, run offshore to Cape May (or all the way to Cape Charles if the weather is really nice). If you want to take your time, go up Delaware Bay, thru the canal and down the Chesapeake Bay.... otherwise go back out. Its ~ 24 hrs offshore from Cape May to Cape Charles.Come in and fuel up at maybe Little Creek, Norfolk (if you want to go back outside) or Tidewater Yacht, Portsmouth (if you want to stay inside). I prefer to stay inside from Norfolk to Morehead City rather than out and around Cape Hatteras. It's a fairly easy 3 day run inside from Norfolk to Morehead/Bauford, if you motor/sail 8 hr days.If the weather is good, go back outside at Morehead City... its ~36hrs to Charleston; ~56 +or- to St. Augustine; and many other possible inlets in between. Staying inside is more comfortable but much slower, more tedious, and you WILL run aground somewhere along the way.If the weather is bad when you get to Morehead City, continue down the ICW to Wrightsville Beach, then go outside at Cape Fear River... or stay inside 1 day further and go out of Wynya Bay (Georgetown). The ICW thru SC and Ga. is long, winding and sholing. Once in Fla, IMHO, it's just as quick and far more comfortable to stay inside down to Lake Worth... then out that inlet, and down the coast to the Keys.Good luck, have fun.... ! !