When the weekend rolls around, Milanese designers, and stylists eager to trade their double-breasted best for a comfy sweater and a Cannoli alla Crema, hop one of the hourly trains from Central Station to Bergamo, a fortified hilltop town 50km to the northeast. The trip is a quick blast through cultivated fields and small villages that deposits weekenders at the foot of ancient Bergamo's walls, which now protect boutique hotels full of the European businessmen getting away from the hustle and bustle of Lombardy's industrial capital. The 48-minute train ride from Milan is the shortest distance between industry and sun-dappled relaxation.

The main attraction in Bergamo is the old hill top "high city" (città alta). Travelers who arrive by train choose to either get a good workout ascending a winding path to the top or wait in line for the funicular that cuts through the rock face and city walls on its way into town.

Though exploring Bergamo can take days, several prominent attractions are just a short walk from each other. The central Piazza Vecchia is a good place to start. Featuring a picturesque ensemble of medieval and Renaissance buildings, including the Basilica of Santa Maria Maggiore, the piazza spreads out luxuriously at the edge of a warren of aging avenues. The 15th-century Colleoni Chapel and the Campanone, a looming tower tourists climb in search of an expansive panorama, loiter just outside the piazza's perimeter. A few alleys further into the maze, the ruins of the city's old citadel – constructed by Milan's famous Visconti family – and the Torre Gambito, a medieval spire, serve as reminders of the town's age. Bergamo's museums, notably the Historical Museum, also include an impressive collections of local archaeological artifacts.

But the city isn't a mere relic. The cafe scene, centered around Caffe del Tasson on the piazza, is buzzing and the annual chocolate fair, held in February, is a caloric three-day hoedown. The town's liveliness is what makes it more than a weekend getaway from Milan. Bergamo is the come-as-you-are city on a hill.

More information: The train ride from Milan to Bergamo costs roughly $5 and takes 48 minutes. Bergamo's Orio al Serio International Airport is now serviced by a number of airlines, including discount carriers like EasyJet and Pegasus.