When its balcony doors close against the cold, Leaf transforms from breezy hangout to cozy cocktail den. Curl up on a tufted leather sofa in the appropriately foliage-filled interior, or head straight to the bar for wintry tipples like the hot tea toddy. Visit from 5pm-8pm daily for $5 draft beer, $7 wine, and $9 cocktails.
Spending time near Herald Square may strike you as an inadvisable, wrong, and bad choice, but this 30th-floor bar elevates you out of the Midtown chaos to a 360-degree view of Manhattan and the Hudson River. Though the indoor rooftop stays open late, plan to visit at sunset for the best westward facing views and #nofilter selfie opportunities.
Though a meal at the Rainbow Room may be out of your budget, the iconic venue’s neighboring cocktail bar will fill you with New York nostalgia without the massive price tag (or at least, a slightly less massive one). The views of Central Park, Midtown Manhattan, and Downtown are almost worth the price of drinks (a gin and tonic will definitely set you back $20).
Williamsburgians pining for views of Manhattan should head up to Lemon’s, the scene-y Wythe Hotel’s rooftop bar, which gets crowded quick on weekend nights. Up top, you’ll find skyline views, DJ sets, and plenty of cocktails.
Exposed brick walls and industrial-style furniture allegedly paying homage to the Garment District’s history welcome you to the retractable glass-covered rooftop at the Refinery Hotel. Note the looming Empire State Building above the bar, as well as the cold-weather appropriate fireplace (should you be lucky enough to earn a spot near the flames). There are plenty of small bites, but you’re really here for the drinks. Pick from their warming Old Fashioned varieties -- each named after a hat in a nod to the space’s former life as a hat factory.
Just a short walk from the New York Public Library, Bookmarks is a literary oasis where you can toast to a day of reading (or taking advantage of the NYPL’s free Wi-Fi) on a roof filled with bookish drinkers. Sunlight pours in during the day, and the place stays quiet even after rush hour, so you can discuss that riveting New Yorker feature with whomever you’re trying to impress in peace.
Long Island City
You’ll have to leave Manhattan for some of the best city views. This Queens clubsteraunt offers sweeping views of the east side skyline and the 59th Street Bridge. The 9,500-square-foot lounge doesn’t really attract the commuter crowd native to Midtown rooftops, but rather Queensians visiting from all over the borough (who aren’t always immune to the temptations of a sushi boat and bottle service).
Lower East Side
This 15th-floor lounge plays to the Lower East Side going-out crowd with cocktails carbonated and bottled in-house, large format drinks that serve 10, and Irving Roasters coffee to keep partiers awake throughout the night. Keep warm with a side of fries, flatbread, or kale Caesar salad (naturally).
Located high up on the 21st floor of Williamsburg's The William Vale hotel, Westlight is home to some pretty spectacular city views, in addition to fancy cocktails and equally fancy bar bites from Chef Andrew Carmellini. Sip expertly crafted libations, stay warm inside on one of the upholstered loungers, or brave the outdoors for its semi-ironic Top of the Rock-style standing binoculars.
Expect to meet plenty of tourists at this indoor penthouse/partially heated outdoor roof deck. Through May, the space is adorned with artificial igloos that fit up to eight. The place fills up fast, and, like most rooftops, it skews spendy, so swing by on weekdays from 2pm-7pm for $7 beers, $8 wine, and $9 well cocktails.