My favorite evening in Milan happened on the Alzaia Naviglio Grande, which is a street that runs along a canal. It started out at a place called Bond Bar. Cool worldmusic, comfortable decor and great caipirinhas and mojitos. They serve a lot of free snacks with their drinks, so one could easily make this place the main event. From Bond we moved to Officina 12, which is located #12 Alzaia Naviglio Grande, of course. Great food. I think I had more drinks there and they were good as well…
For more traditional Milanese food I would recommend La Trattoria del Carmine, although it is a little pricey. It is located on a nice piazza in the older part of Milan.
Near the Duomo I like Agnello, a little Pizzeria/Restaurant that has nice food.
Bond Bar, Via Pasquale Paoli 2, Milano, tel. 02/5810-8375. Closed on Mondays.
Officina 12, Alzaia Naviglio Grande 12, Milan, tel. 02/8942-2261. Closed on Mondays.
La Trattoria Del Carmine, Piazza del Carmine 1, Milan, tel. 02/8646-1234. Closed Sundays.
Agnello, Via Agnello 8, Milan, tel. 02/8646-1654