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Sleight of Hand

Beware of pickpocket sign

Sleight of Hand

I am, by nature, a paranoid person. And I’m extra paranoid when traveling, so I thought we were pretty well-prepared for this adventure. We bought RFID safe wallets to protect our credit cards from being scanned, we know to carry our valuables in front and/or zipped pockets. And we know to leave our valuables at home whenever possible.

We also don’t dress conspicuously. Nobody is going to look at our stretch pants and sweaters and say, “Oh, they have money.” Except for, you know, the computers and iPhones sitting on the table in front of us at Starbucks.

Before you judge — construction stopped us from finding the cafe we were looking for and Starbucks was right there. So I set up shop while Clay ran around the Duomo area. It’s possible that because it was Starbucks, I let my guard down. After all, I’ve worked in hundreds of Starbucks over the last two decades. But not in Milan

When Clay came back, we continued to work and I had my phone sitting to the right of my computer where it always is. In plain sight and right next to my hand, so easily reachable. However, I was distracted putting together meeting agendas. So when the little old lady came up to us and set her piece of paper on the table, I considered her more of a nuisance than anything else. The writing was in Italian, we couldn’t understand what she was saying and we politely shooed her away. 

It was about a minute before Clay mentioned how weird that was. And that’s when I noticed my phone was missing.

Yep, as she was talking to us with one hand, her other hand quite deftly picked up my phone with her piece of paper as she walked away. 

We could see where she was on Clay’s phone, so he went after her. It was only as I sat there waiting for him to return that I realized what a very bad idea that was. Thieves oftentimes work in teams and who knows who was out there waiting for him. In the meantime, I had no phone and no wallet, which meant I had no way of finding him, calling an Uber or even paying our bill. 

Luckily, he came back unharmed, after realizing our cute little old lady had gone underground, literally — into the Metro. After we agreed that it was a bad idea for him to go after her, we had to figure out what to do next. 

a giant Time drain

Luckily, my phone was password and face-protected so my data was safe (I’m pretty sure). I went on to the Apple app to indicate that it was lost (there’s not an option to indicate it was stolen), then we went in search of an Apple store to replace it. There was one nearby so we were able to get a new phone fairly easily. After turning my old phone off remotely, the Apple associate told us that was a pretty common scam and there was really no point reporting it as the police wouldn’t do anything about it. 

Exterior of glass Apple store.
The Apple store in Milan is very cool though.

While we very much appreciated how helpful the Apple associate was, I wish we had ignored that one piece of advice, as you have to file a police report to file a claim with your insurance company. 

The next day, after waiting at the stazione di polizia near our apartment for an hour, we were told which station we needed to go to since we only spoke English. Yep, it was about 10 minutes from where the phone was stolen. Doh. 

The next trip to the correct station resulted in being told it would be two hours to get in, which would have overlapped with our tour. So we planned to go back on Saturday morning (now three visits for those of you keeping track at home) so Clay could run while I waited. Once I finally got in (only one hour later), it was pretty easy to type out the report, though it took me awhile to indicate what country I’m from, as the United States is listed as Stati Unit on official forms in Italy. I found out later you can fill these out online, but you still have to go down to the station to sign them. And I’m pretty sure you can’t make an appointment to do that.

From there, it was pretty easy to upload everything to Faye, our travel insurance carrier. I’ll let you know if anything is actually covered once I hear back.

But the aggravation doesn’t end there. I also got to spend two hours on the AT&T website chatting with “James,” to try and get my phone number transferred to the new phone. As you may have guessed, this is much easier when you actually have the old phone in your possession.

I have also filed a claim with Asurion (AT&T’s carrier) — I’ll keep you updated on that outcome as well. 

Target Destinations shares the top seven places in Europe where you’re most likely to be pickpocketed, and we’re going to (or already have) five of them. Why are they so lucrative? Because there are big crowds of confused people with money there. In other words, a pickpocket’s dream. 

I was telling my friend Stephanie about our experience and she mentioned this video by Pickpocket King Bob Arno, that gives you all kinds of insight into how pickpockets work.

In this National Geographic documentary, a gang of pickpockets demonstrate how they steal.

TLDW? They are students of human nature, they’re smart and they’re fast. 

Related: Wolters shares common places where pickpockets work. 

How Do You Protect Yourself?

  • Be alert everywhere you go. And yes, that includes cafes and bars. We also decided we wouldn’t try to work in coffee shops in busy, touristy areas anymore — we’ll do that closer to home and probably in the same place every time so we can get to know people there. 
  • Carry fewer things so you can keep track of all of them. Unless you need your passport, leave it at your Airbnb or in the hotel safe. Keep your wallet and phone in your front pocket, and use zippers when you can. We had to bring our passports to the police station, so we carried them in an RFID-blocking waist pack (like a fanny pack you carry up front). 
  • Try not to look like a tourist.
    • Pickpockets are looking for people who are confused and distracted. Avoid becoming a target by looking like you belong, though this one can be really hard to pull off when you’re trying to find your way around an unfamiliar area.
    • While the experts advise you to keep your phone in your pocket and listen to directions rather than looking, everyone had their phone out everywhere we went so I’m not sure how much this matters. 
    • They also recommend not dressing flashily or like you have money, but that has also been a very common sight, especially in Milan during Fashion Week.  
    • Leave your selfie stick at home, as they’re basically huge neon signs saying “I’m a tourist.” 
    • Don’t flash around cash (including at the ATM where you should cover your PIN with your other hand). Buy your tickets ahead of time, so there is less need to have your wallet out, or to stand in line in high target areas. 
  • I really, really hate saying this, but don’t trust anyone you don’t know. Pickpockets will work in teams, with one distracting you with an argument, “giving” you a friendship bracelet, spilling a drink on you, or even helping you buy your train tickets, while their partner takes off with your valuables. 
  • Don’t stereotype. While this is a good rule of thumb all the time, it’s especially important here, and we totally fell victim to it. While we did a good job protecting ourselves from the young hustlers on the plaza, our guard did not go up when a little old woman tried to get us to read her piece of paper. And I would not be at all surprised if she didn’t Keyser Söze us. 
Apple map of Ukraine.
Five days after the phone was stolen,
it’s showing up near Ukraine.

If you are robbed, file a police report. Just don’t expect them to get your stuff back, as this is mostly a formality for the insurance company. Cancel your cards (or your phone) as quickly as you can and then start the tedious process of rebuilding. 

I can still see my stolen phone on Find My iPhone and it ended up near Ukraine within five days of being taken. We’re telling ourselves that it has been sent to soldiers fighting the war and they needed it more than we did.

Hopefully the insurance companies come through and this turns out to be a learning lesson, instead of being a very expensive learning lesson. Either way, we’ll keep learning. 

And we’ll keep you updated on what happens with the insurance companies. 

Jackie Shelton, APR, is a strategic communications veteran who, after 30 years still has a hard time focusing on one particular aspect, so she has stopped trying.


  • Yoly
    March 10, 2023

    This is very informative about what to do if pick-pocketed. I’ve seen it so much in the movies but they don’t tell you what happens afterwards. Glad you’re both safe!

  • Jane
    March 17, 2023

    Jackie, so sorry to hear this. I had a similar incident 40 years ago in exactly the same area. Glad you recovered so quickly!


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