Lunch: Osteria Da Fortunata - Navigli. As a first timer in Milan, this was a great place for me to be introduced to the culture. The perfect location to have wine and sightsee at the same time. 

Dinner: Ristorante Bentoteca. The atmosphere is beautiful for a big group or an intimate setting. I highly recommend it because the food was incredible. 

Night Life: Teatro alla Scala. I did not get to go but if I were to go back this would be my ideal place to spend an evening with my wife.

Duomo di Milano - How could you not visit even if it's packed with tourists! It's just too beautiful to ignore! And if you're lucky, you might be even able to hold a pigeon or two.

Fiera di Sinigaglia - As a fan of flea markets and vintage shopping, this is a dream come true for me to spend a day in Milan.

Navigli District - I highly recommend this to really feel the essence of Milan. It's like being in a movie. Everything is beautiful to look at. I can spend hours just sitting and watching my surroundings.