My 5 Craziest Moments in Italy

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crazy italy

What happens in Italy, stays in Italy, right?

NOPE! Not on this blog!

What kind of blogger would I be if I didn’t share the crazy moments along with the all rest? I’ve shared the best hate comments with you guys and even my most embarrassing moment. I don’t know about you guys, but do you ever have an incident and thought “that would only happen to me?” This happens to me constantly, and I seem to be extremely susceptible when traveling. But I digress.

Italy, Italy, Italy. Over the years something keeps drawing me back. I love everything about this majestic, hooker-shaped boot in southern Europe. It’s both predictable and surprising, loud and comfortable, expensive and cheap, and let’s not forget scrumptious. Carbs for every meal of the day? When in Rome, right?! These “only happen to me” moments and Italy seem to go hand in hand. Every time I journey down to this tourist-flocked hub, a hilarious and potentially embarrassing moment is likely to ensue.

Here are the top 5 craziest moments that have happened to me in Italy. 

What’s the craziest experience you have ever had traveling or otherwise? Dish!

crazy italy

1. Milan

Ok, I’m not the biggest fan of Milan, go ahead and hate me. I wanted to love it, but I was far more enchanted by the little towns and villages to the north, like Como and Bellagio, than the smoggy fashion metropolis of Italy. However, everyone should go to Milan at one point in their lives to make the pilgrimage to Chiesa di Santa Maria delle Grazie to see Da Vinci’s famous fresco, the Last Supper. For me this was the holy highlight of my trip last winter in northern Italy, for me than one reason.

And what happened to make that brisk morning so unforgettable besides the 15 minutes spent gazing up in awe of arguably the most famous painting in the world?

crazy italy

A guy grabbed my ass from the back of a Vespa outside said church!

I was stuck at a roundabout with my nose buried in a tiny, maze-like map of Milan as traffic whizzed by me trying decipher which street to head down to the Last Supper church. All of a sudden I heard a loud yell in Italian, and as I peeked my head over my map, a guy grabbed my tush! Looking around in bewilderment, I saw a powder blue Vespa speeding away carrying two young guys, yes that’s right, two men on a Vespa, only in Italy. As my mouth fell open, the guy on the back yelled something else at me and blew me a kiss before disappearing around the corner.

I wasn’t likely to forget that morning.

Ladies (or gents) have you ever had your butt grabbed in public and how did you deal?

crazy italy

2. Venice

Ah Venice, that mythical, romantic, and charming city on the lagoon in northern Italy. I had heard a lot of different rumors, good and bad, about Venice from fellow travelers, but once I stepped off my first waterbus in this sacred city, I fell in love, rain and all. Unfortunately, my friends were right about one thing: the cost. Venice is expensive, no two ways about it. I was paying a fortune for a shared room in a very decrepit guesthouse along with two very cool roommies, one of whom was a very good-looking guy from Australia.

crazy italy

One night we were chatting for hours before going to sleep (in our respective beds, you dirty-minded readers) when I looked down and saw the BIGGEST bug in Italy crawling up my arm. Screaming bloody murder, I flung the sheets off me, hopped up and did the little “get-it-off-me-get-it-off-me” dance around the hostel room on the verge of tears in my pink plaid pajamas and giant geeky glasses, a wondrous and attractive sight to behold, I’m sure.

I didn’t sleep a wink that night for fear of another insect attack on my person but I did become Facebook friends with that guy. You win some and you lose some.

Where have you seen the biggest bug?

crazy italy

crazy italy

3. Florence

I’ve never been good about following the rules. I see something that says “forbidden” but in my head it turns into “not recommended” or “just a suggestion.” This is something I need to work on while traveling, but so far so good, I haven’t gotten myself into such deep trouble I haven’t been able to talk myself out of (knock on wood). One glaring exception to this was Florence.

I flippin’ loved Florence! Firenze in Italian (like that centaur in Harry P.), this city is one of the few that lives up to expectations. Backpacking through Italy a while back, I extended my stay there for almost a week. I hate the boatloads of tourists, so many fellow Americans ick! But I tolerated it for the art and history (remember what I big dork I am? )

crazy italy

Well, my luck ended one cold winter day when I was visiting Michelangelo’s statue of David in the Galleria dell’Accademia. I spent a good 20 minutes just gazing up at it from every angle, just taking it in. How incredible is it to see history come alive? To create something so beautiful from a big chunk of marble that had already been partially carved by someone else 500 years ago? Magical. I was in art history nerd heaven.

After I finished my worship at the feet of this biblical giant, I decided I was going to risk taking a picture of David. There were signs everywhere saying “no photos” but I saw some people sneak some earlier which gave me courage, and in my head I translated “no photos” to “don’t get caught taking photos.” Trying to stand behind a column, I sneakily took my little point and shoot and tilted it up to take a quick pic.

crazy italy

Sneak shot of the Sistine Chapel in Rome, didn’t get kicked out of the Vatican

My first mistake was that it wasn’t too crowded and all of a sudden I heard, “Miss, no photos allowed, give me your camera.” Um, not gonna happen. I quickly shoved my camera in my pocket and tried to play dumb and walk away, but apparently I got caught on this rent-a-cop’s bad day and he wasn’t hearing it. Grabbing my elbow, he proceded to lecture me loudly and drag me out of the Accademia, ignoring my loud protestations of “I didn’t know” and “you don’t understand, I’m one of the only people here who actually APPRECIATES art!” and “I would never take a photo of a painting, but this is a statue and I didn’t have the flash on.” And the worst part was the picture didn’t even turn out well. It was all dark and blurry. Double fail.

Have you ever been kicked out of a place while traveling?

crazy italy

4. Naples

One of my favorite areas of Italy is south of Naples on the Amalfi Coast. I spent a few days there back in 2008 in the spring, meeting up with an (ex) friend from college (who is now dead to me) and also one of the reasons I don’t travel with people often. This area of Italy is spectacularly beautiful, brimming with colorful towns built right into mountain cliffs along the beautiful blue Mediterranean sea. It’s without a doubt one of the most visually stunning places I’ve ever been and almost ruined by the negative cow I was traveling with.

Have you ever traveled or been around someone so extremely negative you think they must have been dropped on their heads as a child? How can you be in such a beautiful place and be so grumpy? I have never been around someone who complained so much, she deserved a prize. After 5 days with this girl, I was on the verge of strangling her the next time she opened her mouth, that or at least throw a limoncello in her face. On the last night we took a very tense train ride back to Naples where we were sleeping in a hostel before flying home the next day.

crazy italy

Seriously, how can you be in a bad mood here?

When we arrived in the chaotic train station, it was after midnight and Naples’ finest were lurking about and being exceptionally creepy. There had been problems in the city with protests and the trash mafia were on strike again so the city was literally filled with garbage and it was raining. Exhausted I just wanted to split a cab to the hostel to rest for my 7am flight, but oh no no no, my lovable travel companion insisted we take the bus (her insistence to take the bus around Sorrento earlier that week ended disastrously and I wasn’t about to go through that again). I finally lost it, and after a few choice words, I just left her in the station and took a cab ride to the hostel alone. And I haven’t spoken to her since, and my world is a better place for it.

I also learned my lesson not to travel with people (girls) I don’t know very well.

How do you deal with negative people on the roa

crazy italy

5. Rome

No matter what, I just can’t stay away from Rome. I spent a freezing January there on a history class trip there in college, and fell in love. Is there anywhere in the world that can match the beauty, intrigue, history or sex appeal that Rome exudes on a daily basis?

At the risk of sounding cliche, remember in Eat, Pray, Love where Liz Gilbert said the word for Rome was sex? S-E-X. I’m wondering if you can guess where I am going with this…

crazy italy

With my college girlfriends that unforgettable winter in Rome, city of sex, we would get dolled up nightly and hit the town. Especially since most of us were under 21, and we could legally and freely drink as much as we wanted. “Yes, I’ll have a liter of sex on the beach, please.” Pun intended.

One night as we were tripping our way back the hotel in high heels, sparkles, and far too much eyeliner, I fell behind the group checking my phone. Being Rome on a weekend, the streets were still filled with people even in the middle of the night. As I walked past a group of older men, one of them turned to me and said something in Italian. Shaking my head and still walking, he said it in English. I won’t demean myself and repeat it here, but let’s just it was not the first time I have been offered a glimpse into the world’s oldest profession.

Really? REALLY?! Getting mistaken for a lady of the night is NOT something a girl forgets. Since then I have toned it down on the liquid eyeliner and rouge in foreign countries, minus Spain, and have thrown out all my hoop earrings.

Has anyone ever mistaken you for being a hooker? Or have you ever been propositioned? If so, I want to hear the story!

crazy italy

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55 Comments on “My 5 Craziest Moments in Italy

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  1. A woman grabbed my man’s legs in Goa while we were on a sun-lounger and I hit her! I didn’t mean to, I just meant to swat her away but she was so tiny that I sent her flying! I felt quite bad after that and bought some ankle bracelets from her! Not sure if that’s quite the same as having your ass grabbed by a guy on a Vespa outside a church!

    This post has been a great read and has given me a very interesting insight into a place I’d love to visit. Thank you.

    And the photos are wonderful.

    1. Thanks Lisa! I just don’t understand why people think it’s ok to touch strangers. Not cool. All these places in Italy are lovely! And really beautiful!

  2. Oh, Rome. I haven’t been taken for a prostitute, but that did remind me of this one time I was taking the overnight train from Vienna to Frankfurt. Sort of proposition-related, I suppose…

    We had gotten on the train and I was in one of the sleeper cars with 3 other people. Nobody really chatted much, since it really was a night train and we were all trying to get as much sleep as anyone can on a bouncy train. But around 3 or 4 a.m. the train stopped and there was some announcement in German that I didn’t understand. Everyone started getting herded off the train and we apparently had to transfer due to some sort of technical issue.

    Half-asleep, I just decide to follow a very chipper, 30-something man who had been in my sleeper car. I consider myself a morning person, but this dude was admirable in his absolute gaiety at such an ungodly hour. He was wearing a shirt from some Venetian animation festival, seemed friendly (see above noted level of gaiety) and I was about to study abroad in Italy, so I struck up a groggy conversation and we made it to Frankfurt on another train without incident.

    As we parted ways at the airport, he says to me in his thick accent, “It was nice sleeping with you.”

    He didn’t quite understand why I was laughing so hard, but bless his non-native-English-speaking heart.

  3. I love these kinds of stories (but only when they happen to someone else haha.) I have never been groped or anything but I was getting off of the bus a few weeks ago in Fuengirola and I saw a guy grab another woman’s butt and at first I thought they had to be together. But then the smack she gave him obviously made me reconsider that assumption.

    When I was in Sevilla for a few weeks, guys would randomly ask me everyday if I had a boyfriend or if I was married. Flattering but… creepy.

    But the craziest thing that has ever happened to me while traveling was that I saw a dead guy hanging off a bridge in Paris. Yeah, you can’t unsee things like that.

    1. Oh, and on that same trip (what luck right?) was when the volcano in Iceland decided to erupt (it also only does so once every 200 years, lucky us). So we were stuck in the airport ALLL day, but we got another week in France out of it. Not too shabby.

      Or this one time I was traveling around Ireland while studying abroad in London and I could not STAND half of the girls I was traveling with, and two of my friends felt the same way. They had to be in control of everything and it was driving us nuts. Lemme tell ya, traveling with 5 other girls is NOT a good idea. Well, one of the days we were there happened to be one of the girls’ I didn’t like’s birthday, and so we were all going to go out to dinner to celebrate. I was okay with this plan until it was suggested that we all chip in. Now, I wouldn’t have minded if I liked the person, but there was no way in hell I was going to do that for someone who I barely knew/cared for. So I lied and said I didn’t feel good and was going to skip dinner, with the full intention of going somewhere else our tour guide had highly reccomended. Yeah, skip to me happily eating alone and the others catching me in my lie when the other restaurant didn’t pan out. (And the rude ones didn’t even want to come back to get me either.) Most awkward dinner ever. And then I puked in the bathroom because I actually was sick. What a weird day.

      1. Yell tell me about it. I was there with my high school and me being the dumb 17 year old I was believed the teachers when they said they were just filming a movie (there were cameras everywhere), but then the teachers later told the older kids that it was real.

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