Baltimore as a destination
The harbor itself does not make for great sailing. It is intensely industrial, and has (very infrequent) large ship traffic which you have to watch out for. This describes the harbor within 5 miles of downtown (i.e., 5 miles from the inner harbor). The Patapsco from the Key bridge to the Chesapeake is very nice for sailing: wide and the occasional ship is confined to a narrow channel. This part is 5-10 miles from the inner harbor. This part is still a bit on the industrial side, but not too bad. The inner harbor is 2.5 hours from the Chesapeake (mouth of the Patapsco).As a side trip on a several day cruise, on the other hand, I think Baltimore is a great destination. You can easily reserve a slip near Fells point in a really nice marina, and there are tons of things within easy walking distance. Little Italy (lots of nice Italian restaurants), Fells Point (nice bars and restaurants), the seaquarium, Pride of Baltimore, the inner harbor proper, shops, and so on. All within 1-2 miles of your marina. Ft. McHenry would probably be a bus ride, since it's on the other side of the harbor from Fells Pt. My wife and I stayed at the Inner Harbor East Marina at Fells Point last October, and had a great time walking around the area. Good restaurants are everywhere, so no particular recommendations.Annapolis is also very nice, but different, and I think it might be harder to get a slip if you don't know what you're doing there (which I don't). Moorings near the City Dock are first-come first-served, and are served by water taxi, but we haven't done it yet, so this is all 2nd hand. I have sailed out of Back Creek (sort of close to downtown, but not downtown), but not from City Dock proper.It is probably a good 6-7 hours between Baltimore and Annapolis, motoring unless the wind direction is perfect. Several pretty creeks/rivers in between to anchor in. I'm sure there are more places to charter in Annapolis than Baltimore, but they're easy to find on the internet. If you had time for a 3-day cruise, then Annapolis to Baltimore and back would make a very nice trip.Good luck. Happy to answer other questions.Jay