The Chessie is a great place to sail, if you're trailer sailing you might want to check out marinas and parks for a base. We used a state park on the Eastern Shore of Virginia called Kipopeke (check spelling) when we had our Hobie 16 although we had to pull it up onto the trailer every night...they really aren't too boat friendly but we made it work and had a great time. Personally we avoid Annapolis, it's too crowded for us but that's just a matter of taste and opinion.