I lived for 20+ years in Delaware and the winters are not the time to be out on the water. Leaving in March is still cold and breezy. I would head
from Lewes up to the C & D Canal and then down the Chesapeake to Norfolk. There are many great and fun places to stop along the way so that any bad weather
does not force you to be out in it 24/7.
- - From Norfolk the ICW south can be a pain if you are in a hurry. But if you are not, then again there are fabulous stopping places regularly spaced for an 8 hour motoring day. And you will acquire the knowledge and lore to share with others who have done the "ditch." If I am not in a hurry I like to do the "ditch" just because it is so interesting and there are so many places to stop and have fun.
- - The Chesapeake, the Albemarle Sound and the Pamlico Sound can offer some challenging sailing as was mentioned by others. Even the Alligator River has been known to snap at boats.
- - The first real decision point is Beaufort/Morehead City where you can go "outside" and sail the coastline as far south as you wish and the weather
permits. Cape Fear/Frying Pan Shoals needs to be crossed just landward of the "R-16" outermost buoy and then you can return to hugging the coastline. I usually make a stop at Charleston as I just love that town. But Georgetown
up the Winyah is also a great little stop.
- - I will do almost anything to avoid the ICW through Georgia
as you snake every which way but south in that area of the ICW. My next favorite stop is Fernandina Beach/St. Mary's Entrance. Love that little town.
- - From then it is either back outside to hug the coastline as far south into Florida
as you wish. Or take the ICW - the mileage is the same - actually a little shorter in the ditch - but - you cannot run the ditch at night and there are the bridges, so the time is significantly longer. But again somehow they managed to space the great stops just the right distance for a day's motoring in the ditch.
- - Going north back to Delaware then going out into the Gulf Stream make sense.