New York may lack the boulevards of Paris, the pools of L.A., or the beaches of Miami, but it possesses one thing those cities are surely lacking: Intense verticality. With that comes views. Accompanied by, as with everything in the world’s hardest charging and stressed populace: Booze. And contrary to popular belief, there are eight months of fine weather to enjoy that enduring combination outdoors. You can also feel free to indulge guilt-free since you won’t ever need to drive—and there’s no surge pricing with yellow cabs or the subway. Add to that sunsets unique to where river meets ocean (the Hudson that is, the East River is actually a misnomered tidal strait that connects the Long Island Sound and the Atlantic Ocean), and the potential of unexpected encounters that only the density of the world’s most diverse city can offer, and you’ve got your summer vacation on top of the world.

photo courtesy of Paul Wagtouicz

First known as the home to the groundbreaking theater experience Sleep No More, which transformed this former Chelsea warehouse into the fictional McKittrick Hotel from Alfred Hitchcock’s Vertigo as a backdrop for an immersive version of Macbeth, complete with (if you’re still following) a participatory bar, it later added a restaurant, and finally a seasonal wonderland on its roof. Morphing from mountain cabin in the winter to English garden in the summer, service runs to highly specific cocktails, like the Blind Love (smoky scotch and homemade tamarind syrup with many dashes of bitters) and Trampled Rose (Finger Lakes rye and amontillado traumatized by ginger tincture and two turns of a pepper mill), which are best downed with bases such as fried cheese curds with hot hot jam and twice fried fries with dill pickle aioli.

photo courtesy of Jimmy James

With seemingly more Europeans than on the continent, the beer garden on top of Eataly, Mario Batali’s gastronomic version of FAO Schwarz across from the Flatiron building, will save you a trip across the drink. A collaboration between three top beermakers, Sam Calagione of Delaware’s Dogfish Head, and, from Italy, Teo Musso of Baladin and Leonardo Di Vincenzo of Birra Del Borgo, the brewery produces unfiltered, unpasteurized, and naturally carbonated cask ales thanks to head brewer Fred Avila. Each ale is served through traditional hand pumps at the perfect temperature to pair with hearty Austro-German inflected Italian fare (think beer braised pork shoulder, housemade sausages and grilled meats). Outfitted with a retractable roof and outdoor heaters, it may be the superior four seasons.

photo courtesy of UNDINE PRÖHL

The beauty of Barcelona but with access to the High Line and the galleries of Chelsea: Star Mexican architect Enrique Norten’s 10-story metal mesh–encased Hôtel Americano offers a glass-enclosed exterior elevator to one of Manhattan’s rare rooftop bar pools. And even rarer one you can actually use without fear of impetigo (you know who you are). Get further into the Latin groove with bebidas like the La Flaca (a frozen margarita with jalepeño-infused tequila), the Citrico (a mojito that adds kumquat to the mix), and El Azul (prosecco, Cointreau, and blueberry purée), which is all you’ll see when you lie back on one of the deck’s comfy chaise longues.

photo courtesy of Wythe Hotel

Take a break from Questlove spinning at Brooklyn’s nearby eponymous alley of Bowl and the namesake Brewery, and head down the street to the borough’s version of the Standard to gaze upon usurped Manhattan from the Williamsburg waterfront. Topping the former 1901 cooperage, meticulously converted into a 70-room hotel while maintaining its original pine beams, masonry, arched windows and cast-iron columns, is the poetically named terrace bar. It’s the brainchild of OG Brooklyn restaurateur Andrew Tarlow (Marlow & Sons, Diner, Roman’s), who runs the booze-and-babe show amongst the work of graffiti god Steve Powers, better known as ESPO, and Morris Adjmi Architects, which provided the stark three-story glass and aluminum addition that rises above.

photo courtesy of Hotel Hugony

Featuring dramatic views of the Hudson River without drama, drinking at the tranquil duplex bar and lounge of the Hotel Hugo is like floating in between the Freedom Tower and Statue of Liberty. Located in the nontouristy part of SoHo some call Hudson Square, the lowkey views come thanks to garage style doors that lead out from a cinematic upholstered bar straight out of a Steven Soderbergh movie. Raise some rosé, you’ve made it.

photo courtesy of Yelp / Elad C.

Find the least conspicuous and most under-the-radar of the city’s airy jewels on the 14th floor of the Manhattan La Quinta Inn in Koreatown. If that sounds uninspiring, look up. That’s the Empire State building hovering over you in all its King Kong glory. Now, look down, the bill says your happy hour shots were only $3. And maybe it’s January, and an abundant garden of heat lamps is giving you a light, outdoor sauté. Now ape the ape and get a classic dark and stormy (Gosling’s Dark Rum with ginger beer).

photo courtesy of The Stand Culture

What was once one of the most exclusive doors in the city, the Standard, High Line has transformed its Dionysian havens into Manhattan’s most reliable warm weather destination. Andre Balaz’s brutalist hotel’s roof contains two independent entities. Le Bain—boasting a notoriously debauched hot tub inside and an Astroturfed terrace complete with crepe bar out—is more Miami than Moscow on the Hudson. Across the way is the more exclusive Top of the Standard, a.k.a. the Boom Boom Room, the very definition of a New York nightclub, where you can literally take in the stars in both senses. Its little known rooftop space pairs cocktails and cabana-style seating with a sunset dining service. The menu reveals the results of a centuries-old white-oak-charcoal barbecue technique invented by Japanese fisherman that heats dishes like octopus with espelette vinaigrette and pork belly with citrus mustard up to 700 degrees. Sizzling.