Mostly it depends on how much driving you want to do. The Portland area would be the easiest to get to and the Mount Desert Island (MDI) area is also great sailing. However, a compromise of the western side of Penobscot Bay (Rockland) would be faster to get to than MDI but an hour or more farther than Casco Bay. However the sailing options are greater from Rockland than just about anywhere else. ou can co SW toward Boothbay and Casco Bay or east to Merchant Row and the MDI area. The MDI area is an additional 1.5 to 2 hours past Rockland, but is the place to sail from if you want to go down east