Have done it both ways...piece at a time or all at once. The reason to do an overnighter is the sailing only gets good once you hit Boothbay (with the thousands of islands)...up to then it's all beach. Once flew the shute all the way...had to take the sales down for the last 10 miles to wait for day break since we got here too soon.
Now down in the Chesapeake and miss the ocean sailing; although, now I sail year round down here. Can't join you, but enjoy the trip.