A Magical Night: Eataly's Ever-Changing Rooftop & A Mad Men-Esque Jazz Bar

When you're feeling any kind of seasonal blues (because in New York, it's very easy to get sick of winter and summer), go to the rooftop of Eataly. Divulge in appetizers and wine in the ever-changing 'greenhouse' on the 14th floor of the beloved NYC food destination. SERRA changes with the seasons, both in decor and in menu items—but one thing can always be counted on...delicious Italian fare and very Instagrammable surroundings.

After, hop over to The Flatiron Room nearby for a dark and steamy nightcap, and a bit of live jazz. This romantic a.f. bar is never super crowded and it lends itself well to sitting close and getting in the mood. You'll feel like you're straight out of Mad Men.