Sleeping with Strangers: Thousands of Miles from Home

I embarked on a solo travel venture to Italy in late August of 2022, visiting four cities in ten days. Traveling solo initially caused a bit of anxiety for me, but conquering these fears provided substantial benefits. I’d like to take you through my experiences with the social side of traveling alone, specifically, sleeping in rooms with 6+ strangers.

There’s one simple fact about myself: I am not the best at small talk. For most of my early childhood, it served as a source of anxiety, a tool I could never quite grasp. Using lines such as “How are you?” or “Where are you from?” always seemed to fall flat, and the conversation quickly fizzled out. However, there are times when these basic questions come in handy, like college orientation or a simple grocery store interaction. Since college, small talk has become much more prevalent in my life, and I have pushed myself to engage in it more frequently. The most recent test of this skill has been my solo travels in Italy, especially when staying in hostels. Documenting my travels has always been a focus of mine, and I enjoy taking photos and keeping a journal of every step I take along the way. 

JUSTIN SHERLOCK // FLAT HAT MAGAZINE

My first stop was Venice — the site of my first hostel experience. To preface, I was fairly nervous and almost considered booking an Airbnb instead. I read stories online of people snoring for hours, having intimate relations in shared bathrooms, and stealing fellow travelers’ belongings in the dead of night. Despite these warnings, I decided to give it a try, and, thankfully, none of these concerns manifested. The worst I encountered was the occasional traveler who wasn’t interested in socializing or left belongings cluttered on the floor. Most everyone was more than willing to talk, and almost everyone spoke English, easing another of my worries: the language barrier. This became apparent when I talked to my bunkmate for the first time, who recommended I dance away the jetlag at the party downstairs. I took her advice and grabbed a free drink from the bar. 

JUSTIN SHERLOCK // FLAT HAT MAGAZINE

JUSTIN SHERLOCK // FLAT HAT MAGAZINE

JUSTIN SHERLOCK // FLAT HAT MAGAZINE

I almost called it a failure until another guy my age walked toward my table, looking as lost as I was. We started with a bit of typical small talk of “Where are you from?” and “Where are you traveling?” Through these seemingly simple questions, I learned a lot about his life. He was traveling from Scotland before his last year at university. A German guy joined our table, and we spent the evening discussing our countries’ cultural differences while enjoying Italian liquor.

After enjoying my first night in Venice, I quickly hopped to the nearest large city, Milan, where my hostel had a more rustic, communal vibe. Even though I never got that close to my dorm mates, talking to them at the end of the day was always a delight. Two of the girls had thick Dutch accents and were constantly talking about how much they wanted to visit the U.S. The other two guys were from New Jersey and were spending the next few months backpacking along the Mediterranean coast. Even though I never partied or traveled with this group, I coincidentally saw one of the girls while on a day trip to Lake Como, which was pretty surreal. I had spent the day by myself, taking trains up and down the lake, and we happened to be waiting for the same returning train to Milan at the end of the day. At that moment, the world felt so small, yet huge, at the same time.

I trekked further to Florence, where I decided to take a break from hostels and stayed in an Airbnb by myself. I spent a day or two seeing the typical sights: cathedrals, museums, gardens. As soon as I reached the statue of David, I received a message from the German boy from the Venice hostel, who excitedly said that he was also in Florence, and we planned to get food at a local market. We spent the afternoon together, bought a couple of bottles of wine, and climbed to the top of Piazzale Michelangelo to watch the sunset. We hiked for almost an hour, talking about life and enjoying the pleasures of drinking in public. We reached the top of the plaza and found about 200 others enjoying the sunset, Florentines and tourists alike.

My last night in Italy was my favorite. I traveled back to Venice and stayed at the same hostel, determined to make one last memory. I was unsuccessful for a while — nobody had checked into the 9-person room. Eventually, my bunkmate arrived, and I struck up a conversation while she was getting settled. Turns out we had more in common than anyone else I had met during my travels. She was from a small town in South Dakota, recently graduated, and had been traveling the world since January. We bonded over the small-town life and met another boy from Toronto, who was traveling before entering his freshman year of university. The three of us returned to the same hostel bar and met a group of five German students, and we spent the next three hours playing card games in the community park, drinking at local bars, and enjoying the company of strangers. We exchanged contact information and still keep in contact to this day.

I realize this is a long narrative about random people that you will never know and never experience in the same way that I have, but what I want to show is that there are so many fascinating people out there. You don’t need a solidified reason to be together. Use the typical small talk conversation starters that you learned in grade school. Nobody will judge you — everyone is in the exact same situation. People just want to explore the world, meet new people, and experience new cultures. Even though the same icebreaker questions get boring after a while, they’re important and set the stage for companionship abroad. Some of these may be short-lasting or permanent friendships, but even if you never see them again, you will forever have stories to tell, even if it’s just grabbing dinner on a random Wednesday night in Italy. Try not to be afraid of the small talk and the newness of it all. Take that leap and meet a random German guy in Italy who knows about a great viewing spot for a sunset.

JUSTIN SHERLOCK // FLAT HAT MAGAZINE

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