High line at sunset - Obvious choice but still magic.the chaos mixture of vegetation art and perambulation and good excuse to see the shows in Chelsea, the light there end of day in autumn is transportive.
Hands down the best wood fire pizza I've had in Brooklyn. Great for a date or if you're feeling fancy schmancy. (Also, don't sleep on the caesar salad here.)
Occasionally I'll look at the Manhattan skyline and wonder what it was like in 1931 when people around the world were saying, "Holy shit, did you hear what they just built in New York?" Just get up there and trip out about humanity. And be sure to keep an eye out for the unmarked locked door guarding a set of stairs leading to a hidden terrace that was originally designed as a fucking docking station for zeppelins.
One of the best curated visual art books in New York and the World, with a bent towards a crossover of music/art/psychedelics. A place to feed the art habit, remembering that the greatest images are still locked in books and not online.
The best part of the new Whitney Museum is the view in all directions from the terrace - and also from the staircase facing West. I'm afraid it upstages the Art.