Milan has a “business up front, party in the back” reputation, and it manages to fit in lots of off-hours fun in its rooftop bars and its swanky cocktail lounges. (Aperitivos are an institution here.) Its chic restaurants—including some ranked among the best in the world—have the same buzz, too. Join the locals cutting loose after spending the day gazing up at Michelangelo’s Last Supper or down from the top of the Duomo. The itinerary I put together below will help you fit it all in.