I have old friends in San Francisco who grudgingly tell me that the High Line is everything that's wrong with New York. Well, too bad. To me, it embodies a culture that's constantly reinventing itself: a defunct elevated railway that was becoming a burden to the city ("we used to climb up there to throw garbage bags full of rotting Korean food at the Hasids!", noted a successful photographer's assistant) becoming a startling example of urban greening for the public good. The expert landscaping makes it feel like walking on a Montauk beach - but a stone's throw from some of New York's most progressive galleries and hotels.
Cobble Hill Cinemas is a cozy little neighborhood theatre. It has all the charm Brooklyn has to offer, screening new releases as well as selected independent films.
If you're far up in Greenpoint and need caffeine + snack, Bakeri is my spot (I say "bake-ery", others say "bach-ery"—I still vote the former). Known for their baked goods—both savory and sweet—it's the perfect spot for a coffee meeting, small breakfast, or a solo book read. There's one large communal table in the center, plus a few two-tops and decent counter space—one of the rare cafes with enough room that it's rarely packed (except saturday!).