PDT, New York
Short for "Please Don't Tell," PDT is the closest to an actual speakeasy you're likely to find in Manhattan (minus, of course, the actual threat of imprisonment). Located inside of Crif Dogs on St. Mark's, to get in you'll need a reservation, which you will give to the hostess by climbing into the phone booth entrance and dialing "1."
If PDT takes the Speakeasy gimmick further than most East Village establishments, it makes up for it in its cocktail selection. The drinks here are expensive, but they're inventive, delicious, and strong. Also, the bar food is a step above most, sourcing most of its food from Crif Dogs next door. The Chang Dog, a deep-dried crif dog slathered in momofuku kimchi, hits every bar food mark and then some (plus, if you're a New Yorker, it will check off your regular David Chang quota).
What to order:
If you're feeling healthy, try the Green Thumb, a refreshing concoction reminiscent of the green juice that your gym is always trying to sell you on, but with more rum (specifically rum, St. Germaine Liquor, celery juice, and green tea, and a cucumber slice garnish). If you're feeling the opposite of healthy, try a Benton's Old Fashioned, which is an Old Fashioned with bacon-infused bourbon, before the bacon trend completely plays itself out.