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People From The Road: Jerry with a J, the florentine lover, foodie Canadians and more stories from my first solo trip

This summer has been a ride. In total I’ve stepped foot on six countries and visited thirteen different cities. Sitting down to write has finally allowed me to reflect on this incredible adventure, one that is still hard to believe it was not a dream. Waiting at the airport gate for my flight home, I am filled with nostalgia that will surely stay present as I write more and more about the places I went to and the things I learned, until my next adventure.

During these travels that took me to Holland, landed me in Turkey, cruised me to Greece and Malta, and led me to Italy I was able to fulfill a life-long dream and a very important step towards my travelling endeavours: I went on my first solo trip in the bellissima city of Florence, Italy. There were a lot of nerves, a lot of worries and a lot of doubts and one of my biggest worries before I set out was how I’d come across to other people; would I make any friends?

A lot of travel bloggers address this question on their blogs. How do you make friends on the road? But the only recurrent answer I always came to was the same: hostels, expat or traveller meetings, networking. What about chance encounters?

As a young solo woman traveller I was advised against any and all kinds of stranger contact aggressively. “Don’t trust anyone.” And I usually don’t, but this time I decided to take a leap and trust my gut. I ended up meeting some of the most incredible people I’ve ever run into.

So, before we get on with the journey, let me tell you their stories.

*Some of the names of the people in these stories have been changed or omitted to respect their privacy.*

Jerry with a J from Estonia

Jerry is the only person on this list whom I met before the solo leg of my trip, and he is on this list because he is just one of those people who really make an impression. He and I met aboard the Equinox cruise ship as it was preparing to leave port from Mykonos, Greece at the outdoor bar because I accidentally bumped into his arm whilst trying to order a drink. We introduced each other, and my first question regarding his name was “with a G or with a J?”. Talk about breaking the ice, huh?

So, Jerry with a J came from Estonia and he worked in real-estate and has basically been all over the world already. He is a very interesting person from the very first time you look at him: not particularly tall but not short either, long pants, polished shoes and elbow lenght striped shirt with suspenders, and one of those ‘hipster’ hairstyles with half his head shaved off and the top of it with a lot of gel. His talk was soulful and he was full of questions; a very curious man who will word his way in until he figures you out completely.

We talked about everything, from a casual “How was Mykonos?” to the weirdest of topics until four in the morning before we said goodbye and went our own way.

The florentine lover

This story is one I will always remember. He was from Albania and he was the first person I met in Florence. It was my second day there, and I was still feeling nervous about being alone, and especially eating alone in Italy (or anywhere, really). For the past day I’d been eyeing a restaurant on my favourite piazza in Florence and ultimately thought it’d be too expensive, but that day I decided to give myself a little treat and asked for a table for one.

As I was leaving the restaurant he is standing at the door: tall, dark-haired and dark-eyes, handsome and with a beautiful smile. I gave him a simple “Grazie, buona serata.” and I’m well out of the restaurant when I hear him:

“Where are you from?”

We engaged in casual conversation for a bit, before he asked me how long I was staying in Florence. “Maybe I’ll see you here again, I work here everyday.”

I saw him  a few more times after that. The next night, two friends and I headed out to a bar, and it wasn’t until very late at night that I finally, properly met him. Who would’ve thought I’d end up walking past the lit Duomo with this gorgeous man by my side? And it was a beautiful, crazy night.

I spent my last hour in Florence with him over mojitos, until it was time to say goodbye.

The sexy italian

It is a scientific fact that any person who speaks Italian becomes 100% sexier. It’s a very sexy language! Well, let’s call him Stefano, he was a young italian man I met through other friends, who praised my horrible italian and polished what little italian I know, and gave me one of the best nights of my life. He was Italian, he was kind, funny and he was cute.

We met after his friends introduced us at the Red Garter, a fantastic sports-bar-slash-nightclub-slash-karaoke that I actually visited twice during my stay and the whole time had a soulful conversation in a mixture of English, Italian, Spanish and French. He bought me a beer and took me to see Ponte Vecchio by night, which is one of the most beautiful Florentine sights, and one of the most beautiful in the whole world too.

Four languages later, a beer, a night-walk, and a couple of cigarettes with him made for an unforgettable night. He showed me a whole other side of Florence that I wouldn’t have known otherwise.

Food-loving Canadian bunch

You will read more about them later, but this group is one I’ll never forget. On my third day in Florence I went on Eating Italy’s food tour on the Oltrarno side of Florence. I was the only solo traveller in the group, and the only stranger, because the rest of it was a big group of lovely Canadians. We instantly hit it off because I lived in Quebec for a year a while back, and they were all super kind and very interested in my stories and what I do.

So, this big Canadian family-of-sorts and I set out on a great food adventure ready to try what is definitely some of the best food I have ever had, and includes two of the weirdest things I’ve eaten: lampredotto and trippe, two traditional Florentine dishes. We learned how to make cantucci, met one of the top players of Florence’s Calcio Storico sport, and ate a lot of great food.

Katie and Maribeth, mother and daughter travelling duo

Katie and her mum were one of the best chance encounters I had. I met them at the Mercato Centrale after they asked to take a picture of my dish and conversation ensued. Katie was showing her mum through Europe, and they were in Florence for a couple of days and indulging in foodie paradise. Now, maybe it’s the food that makes people super kind and talkative, or maybe it was just the kind of awesome people they are, but we had a nice long chat and exchanged pointers for places to go.

It was so nice to meet someone who enjoys travel as much as I do, and they were so easy to talk to. Katie is actually a journalist, so who knows? Maybe one day we’ll read her stories about her travels too. I wish Katie and Maribeth the best of luck with their journey!

The Colombian and the gang

Although I only knew them for about an hour, this awesome group of people from all over were so much fun to hang out with. They were all studying Italian in Florence, and it all started with a couple of very strong Electric Blue cocktails at the Hard Rock Café in Piazza della Repubblica after which we headed to the much-loved Red Garter.

A fun-loving and naturally chatty bunch made up of a super nice Colombian dude who was very much into dancing (and god knows there’s nothing better than a night of dancing), a cool American with a bad-hair-day but a really cool cap and a hilarious Russian girl who loved the Electric Blue as much as I did. Maybe one day I’ll run into them again!

The guys from that stop sign

Them I actually have no idea who they are, but this is my favourite story from my time in Florence because I still cannot stop laughing about it so it is worth a mention. Over the week I ran into two girlfriends from home and we decided to head out and hit the bars one night after going to their apartment to freshen up. We were lost and trying to find their street and basically wandering around following a useless GPS and it was late at night, so every few minutes we’d run into groups of guys who’d either cat-call or stare.

So, we run into one of the latter, and as we are walking past them they say something (I don’t remember what they said), and one of my friends turns around to look at them, and as she turns back to face our way… She face-slaps a stop sign. After the initial three seconds of silence and processing what just happened, the boys and us broke out in loud laughter that continued for the next 15 minutes. We never saw them again after that.

There are a lot more stories, of course, but these were really the ones that struck a chord for me and that truly made my first solo experience special. Every traveller has wondered how to make friends on the road and it’s simple: it will happen. People are more open and a lot friendlier than we usually think, and especially in travel we are all more keen to interact with other travellers. My advice for you? Get out there, and don’t be afraid to say hello.


  1. Pingback: A year in review: 2016, the year most travelled (so far) | Fernanda Was Here

  2. I love this post! I’ve also made many friends while wandering around by myself in strange cities and while most of these were brief friendships, it made my trip a lot more interesting. :) I love the Florentine lover – a lot of my conversations with strangers-turned-brief-companions started with exactly that: “where are you from?” Meeting people is definitely one of the best things about travel. :)

    Liked by 1 person

    • Thank you Liz! I agree, although many may be brief, they were all noteworthy and who knows, maybe we’ll run into our travel friends one day again! The Florentine lover is my personal favourite :)


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