Melissa Case: Best bartenders in Annapolis (and by a large margin). Creative, flavorful cocktails and an elegant assortment of craft beers, both on draught and in bottles. Great sashimi, too! Wowza!
Avery Pistol: Bin 201 has wine tastings on Thursdays and Saturdays (some are free) and a very knowledgable staff. It's one of my favorite places in Annapolis.