Beautiful, chic and fun are all words that can apply to both the Porta Romana district of Milan and the people who come here. Enjoy the area’s boutiques, restaurants and art or simply sit on a terrace and watch as Milan’s best-dressed stroll up and down the street. 

Look away from the clothes and handbags to glance up at the decadent buildings from the 1800s and 1900s that house offices and residences for Milanese elites. Appreciate the more modern architecture of the Fondazione Prada, whose revolving art shows compete with its gold-plated Rem Koolhaas exterior. See contemporary art at the Fabbrica Orobia, an innovative gallery inside a former factory. Attend cutting-edge theater at the Teatro Franco Parenti, known for innovative shows.

The district’s history shines through the Porta Romana, a 16th-century gate on the site of the main imperial entrance historically leading to Ancient Rome. Nearby, the Monument to the Fallen statue commemorates Milanese losses during World War I. Browse for books at the concept bookstore, bar and design shop Open or tour the campus of Bocconi University.

On a hot day, cool off in the Bagni Misteriosi, a public swimming pool with a very Italian statue in the middle. For a more luxurious experience, end the day at QC Termemilano, a thermal pool and spa. Enjoy your Italian vacation with a poolside glass of champagne while looking up at the illuminated arches of Milan’s monumental architecture.

The largely pedestrian Porta Romana is in Milan’s center, well served by tram, bus and subways. Reach it in 20 minutes by bus from the central train station or in 10 minutes from the Milan Cathedral. Parking can be extremely difficult to find, so walk or take public transportation to the area.

On your travels, watch for the vermilion red of Porta Romana’s crest, marking it as one of the historic districts, or “rioni,” of Milan.