Make sure you have a good set of charts for the upper part of the bay as the water gets a bit skinny in places. The entrance to Fairlee is "intersting". You will find details in another thread on the board.
Baltimore is also a possible and you can tie up alongside anywhere in the inner harbor so you could be right outside places such as Hard Rock Cafe, the Science Museum, the Aquarium, Constitution and a number of other places. Canton is also good for bars and live entertainment and the marina there is Henderson's Wharf. The dockmaster is hard to get by phone and it is probably mostly booked this weekend but you could probably tie up on the outside during the day. If you go give them a call on the VHF, the dockmaster responds on that.
With winds from the Ne or SE over the weekend you will have wind over tide at least part of the day so you may get a short chop when that happens.
The tidal flow will be generally South in the afternoon and north in the morning this weekend. Slack water at around 2:00 PM on Sunday. Off still pond the peak flow will be over one knot so your peak chop could be about 3 hours either side of slack.
According to the latest chart updates from 3/6/07 a lot of the navigation aids in the upper bay have been repositioned so if your chartplotter chip is older then the buoys may not be exactly where shown.
If it is a bt rough you could always dodge into the Sassafras and I am sure the ROs based there can tell you more.
