Yeah, for a "guy's weekend" I'm guessing right in the harbor will be where you want to be.
If you arrive on Friday morning approx. 11-ish or so (just before changeover time)... you might be able to get a slip or a spot on the bulkhead at the city docks (Ego Alley) under the Harbormaster's control. (That is NOT the marina named "Annapolis City Docks".)
Sometimes you can get a slip/side-tie at changeover on Saturday's, too... but that depends more on luck. If that doesn't work or you can't time it that nicely, there's usually a mooring ball and water
taxis up to a certain time at night, and there are dinghy
docks conveniently located.
Or Annapolis Yacht Basin (just across the creek, next door to Marriott/Pusser's) is a very good marina... as is Annapolis City Docks on the Eastport side of Spa Creek, just a tad further to walk to downtown.
Lots of marinas
in Back Creek, but the Spa Creek area would put you right in the town center without having to resort to long walks or long water taxi/dinghy rides.