Re: what to do in annapolis
Re: USNA, the grounds are open to the public, you just need your photo ID to show when you walk through the gate. The "official" tour can be interesting and will get you inside Bancroft Hall to see an itsy-bitsy dorm room, but most things on the tour you can do yourself, e.g., the Chapel is spectacular, the Crypt below the chapel is a must-see, the museum is neat, and the grounds are pretty. Most of the tour is outside, btw. Lots of local runners loop though the grounds daily, and you can even take your dog.
I'm partial to Davis' Pub in Eastport since I live in stumbling distance and it's the cheapest drinks in town. The Maritime Museum is also just a few blocks from there, but I've never been. Leeward Market at Second and Chester is a popular breakfast and lunch spot for lots of liveaboards. Boatyard is pricier, but the margarita pizza is good and it's popular for shooters and raw bar (I'm allergic, so no personal view on that). My take is the crowd at Boatyard is more racers and yachties and Davis' is more liveaboards and working stiffs. I've not been to Red Red Wine but have heard some good things. A local band I'm friends with is playing there for NYE, so I'll be checking it out then. If you venture out of downtown, Heroes Pub near West Annapolis has the largest draft beer selection in town and the best pork tacos on Thursday nights. Jalapenos by Towne Center has an excellent happy hour daily offering delicious Spanish and Mexican tapas at $5 each that are usually $10+. Two margaritas there and you're probably feeling pretty festive.
Insofar as it's currently snow and rain, I'd avoid major road trips as much as possible because people here and in DC can't drive for $h!t even when it's sunny. Two snowflakes and there will be accidents everywhere. I'd just walk to lots of stuff in Eastport and downtown; and you can take the e-cruiser electric golf cart thing all through those areas, too; it's free but you tip the driver.
Hope you enjoy your visit.