Just under an hour northwest of Milan is the city of Bergamo, widely touted by travelers who make the trip to bask in its Medieval essence. Made up of the Citta Basa (the more modern, lower city) and the Cita Alta (the preserved, original city), it would take a long day of walking to see all of the centuries-old structures worth seeing, even if you break down and ride the tram that connects the two towns. Because of this, we would suggest spending the majority of your time in the Cita Alta strolling through the Piazza Vecchia, where you'll view 15th century bell tower called the Torre del Campanone, and taking in the medieval Palazzo della Ragione, where you may join the locals eating gelato and hanging out by the central fountain.
Although the lovely pedestrian avenues and squares are a big highlight, you'll truly be missing out if you don't seize a chance to stroll the city walls for a transcendent view of the surrounding Lombardy region and the Alps to the north. Constructed in the 17th century in defense of the Venetian Republic, the atmosphere is contemplative and the views evocative. Even better is the view from the Castello di San Vigilio, positioned just uphill from Bergamo's lovely Cita Alta.