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when we lived there back in the late 80's, it was not unusual to get to town, at least a week or two before the boat show (set up is a week before the sailboat show), to get a slip or mooring, and most of those available were at private residences, yacht clubs and further out of town.

This late in the season you will likely have to find a spot well away from Annapolis, as most dockage will book up years in advance.
 
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