Plunge at Gansevoort Park Ave.

Neighborhood: Flatiron
420 Park Ave. S
Price Point: $$$

This rooftop pool and lounge is an inevitably-crowded three-level party scene in the sky with $15 drinks and a pool floor mosaic of a bikini-clad pinup girl, teasing you with the words “I’m waiting for you.” While tempting, the pool is for hotel guests only. The view is enough to lure you in, so if you’re a guy looking to get lucky, head there on a weekend night when the lounge reaches full capacity with PYTs. If you’re just trying to chill, go early in the week and perhaps pool staff will let you play “just the tip” with your big toe.