Having lived in the centre of Milan (via San Maurilio) for 2.5 years and in Monza, a suburb, for a year, I have many ideas on what to do in Milan. If this city were transplanted in North America, I'd say it's a city so rich with culture and with so much to do that one could spend weeks there. However, in Italy it has a lot of competition, so when people came to visit us, I'd usually suggest spending two days visiting Milan and then using the city as a springboard to do day trips.
Here are my suggestions for the best things to do in two days in Milan:
1) Duomo
Yes, go see the Duomo. Don't miss the roof (see photo of roof detail, below), unless the weather is awful. But here's my Beyond The Obvious tip: if you're taking the Metro (subway) to the duomo, while you're still underground, orient yourself (or ask someone) so that you exit the metro walking up the stairs which have you directly facing the cathedral. The Duomo is perfectly framed during the ascent, and - especially if you've never seen it before - it's breathtaking.
2) Galleria Vittorio Emanuele
Walk through the covered Galleria, which connects Piazza Duomo to Piazza della Scala, and is lined with some high-end and some touristy shops in addition to cafes and restaurants. In the middle of the Galleria you may see women turning 3 times on their heel on top of the well-worn mosaic "Bull's Balls" - evidently for luck in love and happiness.
Don't forget to stop at the intersection and look up to admire the glass dome, an architectural feat in its time.
3) La Scala Opera House
World famous opera house. Check here for the performance schedule and to buy tickets in advance. Last-minute tickets can be purchased by lining up at the box office 2 hours before a performance. One hour before the performance, tickets are 25% off. One ticket per person though. Or visit the inside of the building during the day for 5 Euros.
4) The Last Supper
Go see DaVinci's Last Supper - aka L'Ultima Cena or Cenacolo - at the church of Santa Maria delle Grazie (see photo). Make a reservation ahead of time or risk not being able to get in.
5) Best People-Watching
Via Dante, on a Sunday. The Milanesi dress up in their best and walk up and down this street. If you're there in the winter, try some roasted chestnuts from a street vendor, or get a cioccolata calda which is technically a hot chocolate, but tastes more like a liquid chocolate bar in a cup.
As long as you're on Via Dante: walk to the end and snap a photo of the Castello Sforzesco facade with the fountain in front. You could go inside and see the museum or take a walk in the castle grounds and the huge Parco Sempione but I'd skip it unless you're with kids who need to run around. Definitely do not go into the park after dark.
6) Best Window Shopping
Via della Spiga and via Montenapoleone.
7) Best place to hang out on a warm evening
The Navigli district. The navigli are man-made canals which remain from the extensive network of canals originally built to transport heavy construction materials, like marble. Most of the canals have been covered up, so these days they don't go anywhere, but they provide a nice atmosphere for restaurants, bars, and floating barges (which house restaurants and bars).
On the last Sunday of the month, the navigli district also has a huge antiques market.
Photos by Sanjay
