HOW TO FIND IT Behind a door at the tip of Pier A Harbor House, a photographlined staircase leads you to the bar one flight up. THE VIBE Prohibition-era Havana, when well-heeled Americans would flock to Cuba for its free-flowing rum. TO DRINK From the same folks as the award-winning Dead Rabbit, this newly opened spot features modern renditions of classic cocktails. Order up a sophisticated take on the Cuba Libre: No mere rum and Coke concoction, this version adds amaro, Champagne and Orinoco bitters. 22 Battery Place, blacktailnyc.com
HOW TO FIND IT Enter through the Shakespeare Pub and ascend the stairs ahead. THE VIBE Manor house library, with mahogany paneling and well-stocked bookshelves. A discreet doorbell-like button summons service to your table. TO DRINK Bar manager Meaghan Dorman suggests the Hat in Hand (aged Guatemalan rum, cognac, banana liqueur, angostura bitters). “The comfy room and candlelight scream ‘nightcap’ to me,” she says. 24 E. 39th St., raineslawroom.com
HOW TO FIND IT This second location is mere steps from the original drinking den; enter Japanese restaurant Sharaku and head up the stairs to your left. Confusingly, the owners call this bar by the same name as the first, so confirm which address if meeting someone there. THE VIBE Low-key and Victorian tavernesque, with large windows overlooking the East Village. TO DRINK The cocktail menu is a “greatest hits” of sorts— mainly guest favorites from over the years at the original spot. You can’t go wrong with bartender Ben Rojo’s cocktail competitionwinning libation, The Polished Nail (Chivas Regal 12, Drambuie 15, strawberry, balsamic). 14 Stuyvesant St.
HOW TO FIND IT A bookcase inside French restaurant Chez Moi opens to reveal a candlelit staircase. THE VIBE Romantic, with lush, lavish decor said to have been inspired by Marie Antoinette’s chambers. TO DRINK The cocktail program is by Dead Rabbit alum Franky Marshall. Try the smoky- sweet Guillotine (mezcal, scotch, banana liqueur and honey), named in macabre tribute to the bar’s muse. 135 Atlantic Ave., Brooklyn, boudoirbk.com