I've been though "The Narrows" many times on our 4.5' draft boat with no problems. Take it slow through the chester river entrance and watch that you're centered in the channel as much as possible. Once in the basin on either side of the drawbridge you should be fine waiting for the tender to open the bridge (call him just to be sure he knows you're there, I think they fall asleep once and a while
). There is a good current, I do circles or find that at about 1000 rpm keeps me still. The most anxiety will come as you pass through the drawbridge with what seems only a few feet on either side of your mast
One note: It will be an absolute Zoo over the Memorial Day Weekend, Red Eye Dock Bar attracts many cigarette type boats and other large stink potters that have little concern for sailboats, if it were me I would avoid KN on any holiday weekend, especially if it were my first time?
Just curious, why are you going that way from Annapolis anyway?