If you want to have some fun, you might think about being in Urbanna, VA on the Rappahannnock River for the Urbanna Oyster
Festival 2-3 of November, but I would high tail it away the next day to avoid frost on the cabin deck
top. The drop dead date to be south of Chesapeake is December 15. I have seen it ice in at Christmas
Generally, October 15 is peak snowbird time in lower Chesapeake.
I used to spend Thanksgiving Day in Swansboro, NC and watched a steady stream of snowbirds heading south on the ICW
while eating turkey
I have never done the whole ICW, but I have done from Greenport, NY to Virginia and then parts
of NC, SC, GA, and Fl, and am familiar with the weather
in VA and NC, and I would think that you would want to leave LI between Labor Day and Oct. 1. How much do you enjoy sailing with frost in the morning? Remember, the later in the season, the less daylight you will have for making miles in the ICW. If you do day sailing
only, sun up to sun down, you should be able to make the NYC
to Norfolk run in 10 days of hard at it petal to the metal with no time off for good behavior. Once you get to Norfolk, you should be able to relax a little knowing that you are ahead of the ice, and once you go another 5 days to Beaufort
, NC, you will have all ice behind you. If you want a push like heck,no fun trip, November 1 is drop dead date to leave. I would recommend leaving by mid September if you want your wife to enjoy the trip. This is all assuming you are doing the ICW. Hope this helps.