It all depends on what you're going for... If you're an, "I read Playboy for the articles" kind of person, you may have way too high expectations for this place. Their feature is they're located right on the water, with plenty of people watching, a fun atmosphere, and they also serve food and drinks. The staff are trying to keep crowd control with the masses of people lining up to get an outdoor table. For all that background noise, I think the food and drinks are pretty decent! The charcuterie board was really awesome and made for great app-sampling while having a not-so-awesome sangria. The pizza was decent, and the ?pappardelle was fine.
You come for the view, and a place to chill with your friends, while drinking a bit, and getting full. If Bar Milano was picked up and moved to somewhere on Bathurst or Queen, maybe food quality would be more of a kick-in-the-pants, but for the other perks you get from this restaurant, it's totally worth going to.