Well, my first set of criteria has failed me. (See "Annapolis: Seeking a room w/a view, a martini, & maybe some creme brulee" below.) Restaurants just aren't open late enough -- they mostly close at 10, which is about when we'd be arriving.
What are my options downtown? Classy, not too smoky, live music is good, as long as it's not shout-to-be-heard. Maybe someplace catering to an older crowd?