One of my favourite place for an al fresco drink or dinner in Milan is in the very cool restaurant and bar of 10 Corso Como, Milan’s most important fashion store (sort of the equivalent of Colette in Paris)! Set in a lovely courtyard, it becomes truely magical at night when hundreds of lights lit up the hundreds of plants decorating the walls. The place is also in the middle of Corso Como, a distric full of restaurants, bars and clubs, very popular in Milan. So after your magical moment at 10 Corso Como, you will have not problem finding another place where to continue the evening. One of the best spot for people watching ;)
The nibbles they serve with drinks (a tradition in Milan) are not very generous.. but who’s there to eat anyway! ;) And what do I recommand you to take? A Menabrea, a typical and very good Italian beer.