If you like Sushi or Japanese Tappan cooking go to Joss's. The Rams Head tavern usually has great live music and a good atmosphere.
Mainesail is my good friend and expert in electronics, but listen to a chef here, avoid eating food at Chick and Ruths except to see the pictures and posters and to drink something out of a bottle...the cockroaches are the secret ingredients in their food.
In the last published Sanitation report by the health inspector they received a conditional.
New Years eve is the First Night Celebration.
In years past it meant a lot of neat venues in town like the churches and schools with live music, magicians, plays, storytellers, artwork, and busses for transportantion. It looks scaled down this year for some reason, but the Fireworks at City Doc are cool as are the bars in the area.
New Year’s Annapolis 2012-2013 - Celebrate New Year's Eve in Annapolis, Maryland
If you have the time take at least one day and travel the 35 miles up Route 50 to Washington DC and take in a museum. All the Smithsonians are cool,and free. Take a tour of the Capiol at the Capitol Visitors Center which is also free ( you see all the neat stuff and an awesome IMAX movie) tours are every 20 minutes. Make a free reservation at visitthecapitol.gov. See the national Christmas tree
Goto Baltimore (30 miles up route 97) and see the Inner Harbor and visit little Italy