Centuries ago, goods (and people) floated through Milan on canals with levee systems designed by Leonardi da Vinci himself. Though many canals have since been paved over, the Naviglo Grande and Naviglio Pavese still cut through Navigli, one of Milan’s buzziest neighborhoods and a hot spot for locals and tourists alike. Things to do here include indulging in a canal-side aperitivo (pre-dinner drink), taking a gaudy boat cruise, checking out the historic Washermen’s Alley (Vicolo dei Lavandai), and joining in on the nightlife.
There's no better place to see the sunset in Milan than from one of the bridges over the Naviglio Grande, such as Ponte Alda Merini. Weekends (and most evenings) are usually packed, which can be good if you're after nightlife, but weekdays are better for sightseeing without the crowds. Visit on the last Sunday of the month from 9am to sunset and you'll encounter the Mercatone dell'Antiquariato sul Naviglio Grande, the neighborhood’s antique market.
If strolling around Navigli isn't a right of passage for Milan newcomers, it should be. This neighborhood is relatively compact and built for walking, with waterside promenades, bridges, and masses of outdoor cafes and restaurants fanning out from the main canal. To reach the neighborhood at the southern end of central Milan, take advantage of the city's excellent subway; the nearest metro stop is Porta Genova, serving line 2.
You can find some of the best Sicilian street food pastries in northern Italy at A'Vucciria on the east end of the Naviglio Grande. Just a few euros will get you some of the best cannoli and arancini on the mainland. If you want to try something more unusual, you can opt for heavier Palermite specialties such as panzerotti (savory turnovers) or pane câ meusa (spleen panino).