We have stayed at the Boscolo and found it fit the bill. Nice upgrade for Plats, breakfast included, no CL. The hotel is within walking distance to a number of museums, churches and restaurants. Also an easy train ride up to Lake Como for the day. We stayed on points and were treated exceptionally well.
Convivium- Via Ponte Vetero 21—Brera area, great
Obika=Via Mercado 28—Mozzarella Bar- also in Rome, Florence
Osteria La Carbonella Da Santo- nice quiet, family run,
Al Pont Du Ferr- on the River
Trussardi – by La Scala- nice bar, café, formal dining upstairs
Noon- bar, by Cadorna station
Important to remember, many of the bars, like Noon, and also Obika [which is restaurant] put out huge buffet at happy hour which are complimentary w/ a drink. You could really dine off the buffet, but what would be the fun in that
I have stayed at the AC Milano on two occasions and found it very comfortable and convenient. This hotel is very conveniently situated walking distance to the main train station and the Milan subway and tram systems. This location is also very convenient if you are planning to travel to other cities, such as Florence or Venice, by Italy's terrific high speed trains. The AC Milano is in a non touristy area of the city which we enjoyed. They do not have a CL and provided only a small discount to us as Gold Elites off the price of the breakfast buffet. I think we were given complimentary consumption of the beverages in the room's mini bar. Nonetheless, this breakfast is well worth paying for if it not provided free to platinums or included in your room rate. The AC's treatment of MR elites is similar to that of Courtyards in the US.
As for dining, shopping for Italian wines and foods, and entertainment, I recommend Eataly.
It is walking distance from the AC.
I suggest booking online in advance tickets for viewing the da Vinci's The Last Supper.
The AC in Florence is also a nice place to stay if you are staying in Florence.