Just back from N Italy, 11 days on our own, + 14 days on a RS tour. 99% of the Italians we interacted with treated us fairly and courteously. For those who, like me, feel prudent thinking about the other 1%, here is a summary of things that happened to us and some of the people we traveled with.
Fellow tourer and wife were on a crowded tram in Padua. He saw someone reach for his wife's backpack and intervened to stop it. After leaving the tram he noticed his own phone was gone from his front pants pocket.
Fellow tourer boarding a train in the CT saw a hand dart at her purse, which she was clutching. She shouted and looked up to see a teenage boy shrugging his shoulders and walking away. She then noticed her cosmetic case on the floor. It had been in an unsecured portion of the purse. Valuables were in a zipped pocket and safe.
I was standing in a very crowded vaporetto line in Venice. My left hand in my left pocket containing my "daily cash", my right hand was up on my cross body bag. I suddenly noted a very slight brushing on the front of my right thigh. I turned my head to see a short woman right behind me very busily digging through her purse and then moving away. I had nothing in my front right pocket but a city map and a hanky, they were still there.
RS notes the eating places in Venice between St Mark's and San Zaccaria are pricey. Indeed. Lunched at Trattoria Pizzeria Da Roberto on Campo S. Provolo. We had just 1 bottle of water, 1 bowl of soup and 2 slices of pizza, plus the bread sticks they brought out. Cover charge of 6 euro plus 12% service fee (both noted on menu) brought the total bill to 46.80 euros. Our waiter was unhappy that I wanted the 3 euro change from the 50 euro note I gave him! He didn't even bother to bring me the 20 euro cents. You pay for it when the waiters wear tuxedos! OK, we can read, so its our fault.
Florence has lots of gelato shops, but be careful. RS notes that you pay more for everything in touristy areas. Sure enough. We were in the high traffic area between the Duomo and Palazzo Vecchio. Wife HAD to have a gelato just then. Walked into a shop. Price list said 3 euro for a cone. A 10 was handed over, and only 3 received in change. Sorry too late, she had already bitten into cone. Moral of the story to me: ask how much before you hand over a big bill. We paid anywhere from 1.5 euro to 4 euro elsewhere in Florence for the same cone on other days. For those interested in details the offending shop was at Via dei Calzaiuoli #79, just a few doors to the right of the Disney Store. The high price district. There was no name on the storefront.
Roses. I thought EVERYONE knew about this one, but some fellow tourers learned the hard way. In Venice St Mark's Square. She took the single rose when it was pushed at her. Big Mistake. Then the whole bunch. Bigger Mistake. The pusher asked for payment, and the husband pulled out his wallet. Biggest Mistake. The pusher grabbed a wad of cash right out of the wallet and then proceeded to negotiate how much he would hand back as change. I think they bought the bunch of roses for 50 euros. To add insult to injury, they were then mobbed by other pushers and had to flee the Square.
I wouldn't expect much police help in Italy for stopping pickpockets. OK, I admit knowing nothing about police tactics. However, in the CT incident I noted above, the police became apparent in the CT train stations very conspicuously (with machine guns!) AFTER the attempt. In the US, at street fairs, festivals and so on I see police walking around in the crowds. In Italy I noted the police generally riding through the squares in cars or standing in clusters talking among themselves or checking their smartphones or watching the street entertainers. The few cops I saw walking around in the crowds were typically female officers. That could spawn a whole new discussion.