1) Explore the East Village / Bowery etc.
– have a look at the Cooper Union – interesting architecture
– stop at The Bowery for fireside drinks
– and Death & Co for speakeasy cocktails
– and Backroom is on my list for when I’m next in town – and there are plenty more. A bit further south near Wall Street there’s Dead Rabbit which is also fun – and should have $1 oysters at happy hour.
2) Hang with the Hipsters
Coffee, oysters etc. in and around the ACE hotel 20W 29th St
– http://www.acehotel.com/
– have cocktails in the lounge
– oysters at The John Dory
– and Stumptown Coffee is also nearby
3) Browse some great bookshops
– Bluestockings is at the activist end of the scale – https://goo.gl/maps/A6759znbc5D2
– Housing Works – https://goo.gl/maps/V4PW4TQ4ksm
– McNally Jackson – https://goo.gl/maps/r1cVdYqC7xq
4) Grand Central Station grandeur
– For the architecture… and arguably the food, although, just hopping to Copenhagen might be easier in some ways… but as you’re going to NYC anyway.
5) Jazz
Smalls on 183 West 10th Street is wonderful.
P.S. And don’t forget the Staten Island Ferry! http://www.siferry.com/
P.P.S. Some additional espresso stops here if you need.