Best Flight: The Whiskey Ward
If you have trouble making decisions in the face of too many options, look no further than Whiskey Ward, which offers an incomparable flight program: Choose any three whiskies from a well-curated menu (which includes "New and Very Limited" whisky, too), and for one-ounce pours of each, pay only half of what the total would be for three full shots. You don't have to be good at math or sober to realize that this is not only a great deal, but your best bet for maximizing exploration. 121 Essex St.
Best Cigars: Hudson Bar and Books
With the exceptions of chocolate and questionable decisions, nothing goes better with whisky than cigars. Hudson Bar and Books is one of the few places in New York where you can purchase and enjoy a stogie with your Scotch to bring out your inner James Bond villain. Hudson is the first of three Bar and Books locations in the city (others have followed in Prague and Warsaw) where the decor is traditional and sophisticated, and the collection of whisky is as extensive as it is expensive. 636 Hudson St.
Best Selection: Brandy Library
Those looking for sheer breadth of options should head down to the world-famous Brandy Library. In fact, the bar is worth a visit if only for the opportunity to see and touch their breathtaking Moby-Dick–size menu in person. Don't let the name deceive you, either: While certainly a focus, the brandy selection is only rivaled by the Scotch whisky list—the largest in New York—which quite literally features hundreds and hundreds of bottles, some of which are among the rarest in the world. 25 N. Moore St.