The Barrel Room
Go to the Barrel Room for the wine and the food; stay for the secret speakeasy underneath the main floor (it's called The HogsHead Reserve). Seriously though, The Barrel Room is a great Financial District spot to meet friends or colleagues after work because it has a huge range of drinks available. The rotating wine menu focuses on a new region every three months, and wines are served by the glass or as flights. If you prefer something brown, they have flights of whiskey as well. Win/win.