When you step out onto the rooftop at 230 Fifth—20 or so stories above the city sidewalks—Midtown's buildings rise up all around you like a forest canopy of stone and glass and light, with the Empire State Building looming over them all. You don't need to be holding one of the bar's boozy hot chocolate or neat scotches to enhance the view, but they certainly don't hurt.

Equally tongue-tickling is the menu's small bites and entrees, which Miso Glazed Salmon as well as Macaroni and Cheese Sampler. These delights can be savored along the miles of tables and couches indoors—all illuminated by candles and lurid purple lights—or amid the umbrellas and lush greenery of the outdoor garden.

During the months when sweaters are an acceptable form of currency for taxi cabs, one might think the scene at 230 Fifth dies down. Not so. The roof is partially heated during cold snaps, and the penthouse floor below offers its own impressive views and stays open year-round.