Pickpocketed in Florence? My Real Attempted-Theft Story + the Anti-Theft Gear That Saved Me

I travelled through Italy as a solo woman in my forties, and on my way to Florence Airport I was targeted by a pickpocket on the tram. Nothing was actually taken — but it was a genuine professional attempt, and it happened in seconds. In this post I share exactly what happened, the mistakes I made, and the anti-theft gear that saved me. If you are heading to Florence, Rome, Milan or anywhere in Italy, I hope my real experience helps you stay safe.

My Attempted Pickpocketing in Florence

It was late June, and I was heading from central Florence to the airport on the tram, alone, with a large suitcase. I thought I had prepared well: my passport and backup cards were in a security pouch worn under my T-shirt, my phone was on a crossbody sling, and my everyday wallet was inside a zipped crossbody bag. Just before boarding I even double-checked that the zip on that crossbody bag was fully closed. And yet, the moment I stepped onto the crowded tram, a professional pickpocket went straight for it.

4 Mistakes I Made That You Can Avoid

Looking back, I made several small mistakes that, added together, made me an easy target. Learn from them:

1. I changed my boarding station at the last minute. I switched from my planned stop to Santa Maria Novella — which, I later learned, is one of the most pickpocket-prone spots in Florence. Unfamiliar stations make you hesitate and look lost.

2. I wandered around the station with my suitcase while looking at my phone. A solo traveller, clearly distracted, dragging luggage, is exactly the profile thieves look for.

3. I let my guard down chatting with another tourist. A friendly Australian woman struck up a conversation, and for a few minutes my attention drifted. Thieves love a relaxed, distracted target.

4. I boarded a crowded carriage — and the rear one. Crowds let thieves press against you unnoticed, and the rear carriages of trains and trams are statistically the most pickpocket-prone.

The Moment It Happened

Seconds after I boarded, I glanced down and saw that the zip on my crossbody bag — the one I had just checked — was open, and my wallet was halfway out of the bag. My heart stopped. I immediately looked around, glaring, and checked the contents: my 20-euro note and the credit card I had used to buy the ticket were both still there.

Why did the thief fail? Because my wallet had a small ring on it, and that ring was attached to a sturdy retractable tether clipped inside the bag. When the wallet was pulled, the tether held it back — so it only popped halfway out instead of disappearing completely. I never felt a thing. That is how fast professionals work.

The woman standing behind me — casual bag worn across her body, eyes on her phone — got off at the very next stop, exactly as I suspected she would.

The Anti-Theft Gear That Saved Me

Here is the gear I actually used on that trip, and why each piece mattered. This is not theory — this is what protected me from a ruined holiday.

1. A hidden security pouch worn under your shirt

My passport, spare credit card, and most of my cash were in a slim security pouch worn against my body, under my T-shirt. Nothing in it could be reached. If your passport is stolen in Italy you would have to travel to the Japanese (or your country’s) consulate in Rome to replace it — so keeping it hidden is non-negotiable. I recommend a thin shoulder-style pouch rather than a bulky waist belt: it stays flat under clothes and is easy to access at airport security.

2. A wallet with a ring + a strong retractable tether

This combination is what literally saved my wallet. A wallet with a small ring, attached to a sturdy retractable tether (leash) that clips inside your bag, means that even if a thief grabs it, the wallet cannot be pulled free. Skip the flimsy 100-yen-shop versions — buy a strong one that extends smoothly but not too far.

3. A zipped, lightweight crossbody bag

For the small items you need to reach often — coins, a low-value note, your ticket — use a zipped crossbody bag that is NOT an expensive luxury brand (designer bags attract attention), is lightweight, and ideally has an interior and a back pocket. Keep it in front of you in crowds.

4. A phone sling you wear across your body

In Italy, phones are snatched in a heartbeat. I kept my phone on a crossbody sling strap at all times, which meant I could take photos without opening my bag and never set my phone down. It survived the pickpocket attempt completely. Choose one that works with any phone model and stays attached even with a case on.

One more small thing that helped: a smartphone ring (grip) stuck to the back of my phone. It loops over a finger so the phone cannot be snatched cleanly out of your hand, and it stops you dropping it on cobblestones or down a tram gap. It pairs perfectly with a crossbody sling.

5. A lightweight, Japanese-quality suitcase with smooth wheels

Italy’s cobblestone streets are brutal on cheap luggage. A lightweight case with sturdy, smooth-rolling wheels and a stopper made moving — and standing still on a moving tram — far safer and less stressful. When you are not fighting your suitcase, you have more attention for your surroundings.

My Top Anti-Theft Tips for Italy

1. A hidden security pouch is essential. Keep your passport, backup card, and large cash against your body, under your clothes.

2. Tether your wallet. Attach a retractable leash to your wallet and clip it firmly inside your bag, so it can never be pulled free.

3. Keep your phone on a crossbody sling at all times — it doubles as theft prevention and a way to avoid leaving it behind.

4. Carry only small change in your outer bag for tickets and drinks, and wear that bag in front of you in crowds.

5. Wear a backpack on your front in busy stations to shield your outer bag even further.

6. Stay visibly alert. Thieves avoid travellers who clearly notice their surroundings. Keep your head up, especially with luggage near stations and on crowded trains — the airport run is a prime target window.

Shop Anti-Theft Travel Gear

Everything that protected me, in one place:

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Plan the rest of your Italy trip:
🧳 Italy Packing List: What to Bring + Malpensa Transfer
👗 What to Wear in Italy in June: A Complete Packing List for Women
🗺️ Lake Como, Italy: The Complete First-Timer’s Guide
🧴 Santa Maria Novella Florence: The World’s Oldest Pharmacy