Milan is Italy’s quiet triple threat—capital of fashion, finance, and design. Begin at the heart of the city in the Piazza del Duomo; the rest radiates outward in a mosaic of neighborhoods where history, art, and fashion overlap. Walk around the tony Brera neighborhood and peruse the shops of the Fashion Quadrilateral, literally a rhomboid dedicated to the world’s best designers. Head to Navigli for a cocktail when the sun is about to set. Wander the Isola neighborhood for homegrown designers and unique boutiques. By night, Milan’s marble and modern architecture is incandescent, so between aperitivi, make sure to stop and take it all in.