I'm 5 minutes from Baltimore and I can't really compare it to Annapolis. It is *my* opinion that Annapolis is more boring. Baltimore is one of those cities that has great parts and bad parts. The Inner Harbor is nice...the Aquarium is there and lots of nice little shops. Little Italy has GREAT Italian food and is absolutely worth a dinner or lunch
. Fells Point and Canton also have great little pubs, etc. The best part about it is that you can pretty much reach any area worth spending time in via the water taxis. They run all day until I think 11 at night ( on weekends, not sure about daytime).
Don't get me wrong Annapolis is a very pretty city on the water with expensive home and nice shopping but there just isn't as much to do...unless of course you know someone with a boat, etc. Then again..the Naval Academy is there and you often see really cute cadets walking around...ha ha ha.