I spent two seasons at Havre de Grace and I really enjoyed the town. For me it was a great introduction to the bay, and a world of difference from sailing the Delaware River. The town dock is definitely the best deal in town as far as marinas and the promenade has great cheeseburgers and milkshakes. There is a great triangle for day sailing from the Town marina across to Perry Point and up to the bridge. Just got to watch for the moored barges. Up the Susquehanna theres some nice sailing also but you cant go too close to the dam, it gets a bit thin. Traveling down the channel to the bay can take quite some time and it is narrow. I've hit bottom a few times just a few feet outside the channel, but fortunately its soft mud. If you want to go anywhere, Sassafras, Worton's Creek, Fairlee Creek, or Still pond, it is a very long trip to get there at 5 or 6 knots.
If I can make a suggestion, not knowing where you live, check out the Middle River area. Marinas are plentiful and reasonably priced. A large sailboat community resides there and theres great sailing and quick access to the bay. If I motor at 5 knots I can make it to Fairlee in about 2 1/2 hours, sailed back in a good blow once in under 2! Rock hall is about 3 1/2 hours at 5 knots (made it back in 3 hrs in a good blow with too much canvas up), Baltimore inner harbor 4 hrs at 5 knots. Annapolis is not too far either, I think about 5 hours.
The drive for us was only an additional 20 minutes further than HdG but well worth it for the sailing. That being said I do miss the town, but there are nice restaurants and other attractions around Middle River, like a drive in Movie theater! There are at least 3 or 4 restaurants that have slips so you can tie up and have dinner. At Hart Miller island (a very popular spot to anchor and swim there is a boat that comes out and sells all kinds of food.
M