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We are thinking of visiting Milan next month with my family which includes two teenage daughters. I am led to believe the area around Milan central train station is frequented by prostitutes so is there any other areas we should avoid staying in to avoid unsavoury characters.
The area around the Central station area isn't the prettiest but it's where most of the hotels are, it's quite safe because there's a high presence of police there and I don't think I've ever seen prostitutes there contrary to the Corso Buenos Aires area where I've seen them often quite early in the evening.
Unfortunately, Milano Centrale FS train station is quite an unsavoury place at night at the rear as it seems to be a major hang-out for the down-and-outs, alkies, dossers and general wasters sorry to be so descriptive, but you get the idea rather than people who just want to start trouble for no reason. However, in general Milan is pretty safe even late at night around the station and you should go about your business without any paranoia.
Obviously you should always keep your wits about you and always keep an eye on your belongings. My strong advice for you is to be very vigilant when obtaining tickets at the ticket dispensers in the metropolitan underground stations as the gypsies are a nuisance and pest, plus the stations are rife with pickpockets.
As regards the prostitutes, I don't think you would see any in the usual tourist locations. I think that as parents and grandparents we are usually more concerned about our own embarrassment being with kids when unsavory characters are sighted. However, I learned that unless they have been locked in a closet, teenagers are way ahead of us with worldly knowledge, and seeing some of reality is not all a bad thing.