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Snag a View From The Top of 14th Street at Skybox

Bar owner Ian Hilton is taking 14th streetgoers up to the luxury box at his new rooftop bar, Skybox. Located above his cool, 70s retro arcade lounge, Players Club, is a sporty addition to the Hilton empire (no, not that one). 

Enter through the basement bar and pull a ticket from an old-school deli counter and wait for your number to appear on the “now serving” sign. Someone from the bar will escort you to an elevator where you’ll have to finish your drink before getting aboard. 

While you wait for the elevator, you’ll be forced to feel bad for the tenants who live in this otherwise residential building on 14th who probably never expected to have to share their lift with a bunch of bar patrons. But once you’re up on the rooftop, you might just forget any moral quandaries you may have had. 

Skybox is a nod to stadium luxury boxes, and carries that sporty theme into a colorful mural of a basketball player. A small indoor space and bar opens up to a surprisingly spacious patio with views up and down 14th Street.

The patio is equipped with a variety of seating options, from cozy couches, to hightop tables and a ledge perch that is perfect for people watching. A large awning and heaters make it ready for less than ideal weather. 

The tight bar menu leans heavily on bottles and cans, but the cocktails are done exceptionally well. It was the best mojito I’ve had in awhile. There’s no food available but remember that you can order from the neighboring Shake Shack and have it delivered to Players Club below. 

Skybox is a fun place to see and be seen this spring and summer. Catch us drinking a draught while people-watching over 14th Street on a sunny day soon.


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Annie is the lead social media manager for Bitches Who Brunch. Chances are, she's ordering the chicken and waffles.

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