Classic Italian & Cheap Comedy At The Pit—Match Made In Heaven

A night well done in Gramercy should include consistently delicious Italian food (courtesy of Giorgio's) and a healthy dose of musical theater hilarity (at the People's Improv Theater, of course).

Start at Giorgio's of Gramercy for classic Italian food at a good price. Arrive between 4 and 7, and select specialty cocktails, homemade infusions, wine, beer, and bar bites are all yours for just $4-7 each. Clever, ay? For food, we recommend sharing the roasted Blue Point oysters, the baked macaroni with chorizo, and the garlic mashed potatoes on the side.

Next, bounce over to The Pit where you're bound to run into up to 10 shows a night. Beginning around 6 and ending around 11, there's always something on stage to entertain the two of you.