Assembly is the coolest rooftop bar in Philadelphia. It has pretty much everything you could want from a place where you go to drink outside on top of a building - from good cocktails and a great view of downtown, to semi-circle couches that you can throw your belongings across to save seats for friends who may never show up. There’s also an indoor portion of the bar that’s open in the winter, and when it’s warm enough they’ll just turn the fire pits outside on full blast so you can pretend the groundhog either did or did not see its shadow - whichever means that winter is almost over.
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If you’re looking for some good Neapolitan-style pizza in a casual space, go to Pizzeria Vetri.
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Sunset Social is essentially a lawn on top of a parking garage in University City with burgers and frozen drinks.
Irwin’s is an indoor/outdoor bar in the Bok Building in South Philly that serves Mediterranean food along with solid cocktails.
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