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.
Best Authentic Scottish Experience: Highlands
Conversely, Highlands does, in fact, offer about as much legit Scottish culture, food and beverage as its name suggests. Owned and operated by Scots, the restaurant serves phenomenal Scottish fare alongside Scotch cocktails such as the Rob Roy and Blood and Sand. That's not to say you can't just saddle up to the bar and pick out a few neat aperitifs from their impressive Scotch list, but you'd be making a huge mistake visiting without ever digging into the haggis (sheep organs boiled in a stomach) with neeps and tatties (turnips and potatoes). 150 W. 10th St.
Best Beer Back: d.b.a.
It's easy enough to get distracted—and subsequently hypnotized—by the absurdly impressive beer board at New Orleans–themed d.b.a. But after your initial visit or two, do yourself a favor and give the whisky a try. For a bar boasting 16 taps and 150 bottles of fresh beer, this place also has plenty of solid single malt Scotch to go around, including your favorite Glens, a few delicious smoky Islays and a few rare exclusives, such as Aberfeldy 1978. 41 1st Ave.
Best Live Music As You Sip: The Flatiron Room
Between the wall of caged whiskies, library ladders, dimpled booths and candlelit cocktail tables, you'll convince yourself you just hopped out of Doc's DeLorean into the 1920s when walking into the Flatiron Room. Best of all, on the red-curtained stage is a nightly performance from a rotating roster of old-timey jazz bands, complete with a sultry singer fronting each group. Yes, the whisky selection dares to rival that of the Brandy Library, but you'll be coming back to this one for the sheer enjoyment of being able to experience another era for the evening. 37 W. 26th St.
Best Cheap Drinks: Blue & Gold Tavern
Got a thirst that needs a quenching, and only $5 to show for it? If so, Blue & Gold is your spot. The prices at this dive bar are so low for New York City, you'll think you're either hallucinating or have wandered into another state. But the dream is real, and for years, the bar has offered glasses of Highland Park, Laphroaig, Dalmore, Macallan and others to all customers for only $5. All this, and a working jukebox to accompany your pool-playing. The only drawback is that you'll hate spending money in every other bar after being spoiled here. 79 E. 7th St.
Best Food: North End Grill
Owned by Danny Meyer (the restaurateur responsible for such New York staples as Gramercy Tavern and Shake Shack), North End Grill is a welcoming establishment that features a dinner menu as classy as its whisky list. Offering over 150 different types of Scotch, as well as half a dozen (albeit, pricey) single malt cocktails (try the Penicillin, made with lemon, honey, ginger, and Islay Scotch), this is the ideal place to celebrate the completion of your whisky tour with a delicious meal and drink. 104 North End Ave.