10/07/2026
I usually love sharing all the fun, beautiful parts of travel, but I think it’s just as important to share the not-so-glamorous side too.
Meaghan shared our experience from the last couple of days of our Italy and Greece trip, and I wanted to share it here as well because this is such an important reminder for travellers.
The biggest thing for me is that we were aware of pickpocketing. We had talked about it, we knew it was common in busy tourist areas and we thought we were being careful. Meaghan was even wearing her crossbody bag in front of her. And it still happened so quickly.
It was definitely an eye-opening experience, and after spending our final 48 hours between the police station, changing flights and getting to the Canadian Embassy in Rome, I learned a lot that I’ll now be able to pass along to my own clients.
This absolutely would not stop me from travelling to Italy again. We had an incredible trip and made so many amazing memories. But it is a reminder to stay vigilant, especially when you’re distracted with luggage, crowds or transportation.
Travel isn’t always just the highlight reel, and sometimes the experiences you never planned for end up teaching you the most. ❤️✈️
Definitely give Meaghan’s post a read, especially if you have an upcoming European trip!
I usually share the highlights of travelling—but this part of my trip deserves a place here, too.
After a wonderful Italy and Greece cruise, I was pickpocketed on our last night in Venice. My passport and credit cards were in my crossbody bag, worn in front of me. We had just stepped off a water taxi, and I was manoeuvring my luggage on a bridge when a man repeatedly stopped in front of me, seemingly trying to take a photo. I now realize he was slowing me down so someone could get into my bag from behind me.
It felt strange, and I was actually yelling ‘excuse me’ multiple times as he would not get out of my way but it allhappened so quickly. By the time we turned the corner, I realized what was missing. We hadn’t even reached our hotel which was only a 5 minute walk away.
Instead of flying home to our families the next day as planned, we cancelled our flight and took a four-hour train to Rome to visit the Canadian Embassy when it opened Monday morning.
There were tears, phone calls, paperwork and unexpected expenses. Thankfully, I received my replacement travel document within six hours of submitting my application.
As a travel agent, I’m used to helping others prepare for their trips. Being on the other side was a reminder that experience and preparation don’t make anyone immune to something going wrong.
My takeaways? Keep copies of important documents somewhere you can access separately, have a backup payment option, and give yourself a moment to regroup when moving through busy places with luggage. I’ll also be reviewing my own travel insurance coverage much more closely as I was disappointed to learn that trip interruption caused by a stolen passport is not something that is covered.
And the biggest thank-you goes to my travel partner, Jaimee, who stayed by my side through it all. Having someone there while you navigate a stressful situation far from home means more than I can say.
I’m still grateful for the beautiful memories we made in Italy and Greece. This was a difficult ending to a wonderful trip—and an experience I wanted to share honestly, because travel isn’t always just the highlight reel.
