Alright, so I reccomend that you don't go to drink. I assume you'll be with the wife. It is a great cocktail bar. In fact it is technically the best cocktail bar in America. That said it isn't the best bar. Am I also correct in assuming you like drinking whiskeys neat? If so there are way better places you should check out. I have a few beefs with drink. 1.) those mother fuckers are boring and have 0 personality. 2.) You can't really bar hop there 3.) Access to public transportation isn't that hot. I don't think you are a cocktail geek, right? Go to Saloon in Slumberville. One of the best whiskey bars in the country. Plus there is a shitload of other stuff around there.
My three main areas to drink are Central Square, Harvard Square, and Kenmore. Each has at least one really solid place to eat, one solid cocktail nerd bar, and a few other mediocre cocktail bars, plus other forms of entertainment. I will warn you I am more partial to Cambridge than Boston. i think there is a more exciting mix on that side of the river.