Solo Travel, Self-Confidence, and the Tuscan Sun
From one writer's first solo trip.
Hello and happy almost June, friends! Can you believe we’re here already?
A few months ago, Substack writer in the UK, of Letters of Everyday Romance, and I connected about an upcoming solo trip she was doing—her first one ever, for an upcoming retreat.
Solo travel can be daunting, and I know that even I chicken out from time to time, so I wanted Jenna to share about her experience in real time. How was your first solo trip? What do you wish you’d done differently? Were there times you had peak anxiety?
The below is the result of that conversation and her trip to Tuscany—it’s lovely and immersive, but most importantly, it was a wonderful reminder of how empowering solo travel can be. Thank you, Jenna, for taking the time to write this and for giving us the courage to explore the world solo. x
How I Finally Found the Self-Confidence I'd Longed For Under the Tuscan Sun
For quite some time, I had been longing to attend a retreat of some form, scouring the web in search of the perfect one. I knew I wanted it to be centred around writing or poetry. Stepping back in time to one sunny morning in July last year, I stumbled across a post from announcing her creativity retreat in Tuscany—an absolute dream. I think the universe had certainly gotten the memo; the day prior, I had been journaling about trusting that the right retreat would find me. Talk about divine timing!
The moment I read that post, my soul knew I had to be there—although it didn’t come without a few challenges along the way.
So, what does all this have to do with travelling solo?
After eagerly booking my spot, I knew that I would need to spend at least one night in Florence prior due to flight times. I had a handful of potential travel buddies lined up to spend a few days in Florence with (my Mum included—the best travel buddy), however, thoughts kept popping up in my mind about how I had never travelled alone before and how it was always something I had wanted to do.
Due to varying circumstances, my potential travel buddies couldn’t make it, and so those solo travel thoughts kept getting louder and louder. Should I spend a few nights in Florence solo?
In the end, I took the leap and I settled on two nights in Florence, arriving mid-afternoon, so I’d essentially have two full days in the city before the retreat. I knew I wanted more than one night, as I wanted to explore, wander, and eat to my heart’s content. But it also ensured that my entire trip wasn’t longer than a week.
As someone whose constant companion is anxiety (hello there, fickle friend), I knew that this trip wasn’t going to be without its fair share of panicked moments and stepping out of my comfort zone. Like when I arrived at the airport the morning of, and needed some time to compose myself and stop the thoughts of “what on earth am I doing?!”
Thankfully, my first flight from Birmingham, UK, to Frankfurt, Germany went smoothly, and I felt the huge weight begin to slowly slip from my shoulders. Because, to add to the challenges of this trip, I decided to fly from one of my local airports, which included a connecting flight in Frankfurt—something I also had not done before, solo or otherwise—to avoid needing to head down to London for a direct flight. I think heading to London would be an easier option in the future; I guess you live and you learn!
In the weeks leading up to the trip, I had heard horror stories about people missing flights because of endless gate changes in Frankfurt or from having very short connecting times, which only added to my mounting pile of anxiety. So I was hugely relieved when I made it to my gate for my flight to Florence with plenty of time to spare, and even had time to grab a delicious sandwich, journal, and do some much-needed skincare.
One key for my trip was ensuring I felt safe, or as safe as possible. Before I left, I downloaded the app Life360, so that my family could locate me. I also researched different restaurants and places to visit, spent endless hours staring at Google Maps and pinned various places close to my hotel. Ensuring I was as familiar with the area as possible was really important to me.
I chose a hotel that was a 20-minute walk from the Santa Maria Novella station, so it was easy to get to, and also one fairly close to the Duomo, rather than on the outskirts of the city. I felt safer being closer to the tourist hotspots, but I could also wander during the day and find a few hidden gems. The hotel I chose also had a rooftop (something I can’t resist), which meant that if I didn’t want to stay out late at night (something I knew I wasn’t likely to do), I could grab a drink and still take in the vibrancy of the city from above.
Upon arriving in Florence after another smooth flight and a tram journey, I walked the short distance to what I can only describe as the best sandwich place ever (highly recommend SandwiChic if you ever find yourself in Florence!). I met up there with another writer who was also attending the retreat.
After a brief getting to know one another more, we parted ways, and I wandered to my hotel. In that moment, it washed over me—I couldn’t actually believe I’d done it! I was in Florence, solo! It was a moment of sheer joy, pride in myself, and a quiet confidence that I had managed to navigate two flights, a tram from the airport, and find my hotel down one of the many narrow side streets, all on my own. All the anxieties were somehow worth it for that feeling of pure elation.
The sun was shining as I headed back out onto the streets to further familiarise myself and go for a well-deserved glass of wine. I spent some time in a small piazza, drank wine, and wrote in my journal to keep me company (a must if you’re travelling solo!), before heading to the Odeon—a cinema, bookstore, and cafe all in one. A writer’s heaven. I then ended the evening on the hotel’s roof terrace, and video-called my family to let them know how my first day had panned out.
The following day, I had quite a packed schedule with places to see, a tattoo appointment (to mark the occasion, of course), a rooftop lunch reservation on the other side of the Arno River, and plenty of sightseeing. I have a handful of small tattoos (some from other trips), and I knew I wanted to mark the occasion of my first solo trip with one. I chose a dainty lemon design with “dolce far niente” (the sweetness of doing nothing) underneath, to remind myself of life’s small pleasures.
Just the simple act of grabbing a croissant on my own in a foreign country was something I hadn’t imagined I’d ever feel confident enough to do. And I proudly took my croissant, found a quiet bench near the Duomo, people-watched, and felt this new sense of contentment settle inside my soul. I even took some solo photos inside one of the city’s many Foto Automatica photo booths, something again that I wouldn’t usually have felt confident enough to do, worried I would be judged for being alone.
I think choosing a city for your first solo trip is such a great way to ease yourself in, because it’s true what they say about cities—you’re never truly alone. I may have been wandering the streets by myself, but I felt the immense hum of community and culture around me.
I felt a slight pang of sadness on my last solo morning—I would’ve loved another day to keep exploring the city, and my newfound sense of self. I know in my heart that travelling solo is something I will do again.
I loved pairing my solo travel alongside the retreat, it gave a perfect balance of solitude and connection. It was my first retreat too, and I’ve vowed to myself that I will try to attend one every few years. P.S. If you’re looking for a retreat, Aweventurer is the place to look! Absolute perfection from start to finish.
Overall, I found the trip to be both life-changing and life-affirming, in the best possible ways. I gained the self-confidence I have longed for for years, but also a sense of overwhelming gratitude for my everyday life. A perspective one can only gain through travelling somewhere new—and especially solo. Travelling solo has allowed me to believe that I can do hard things. And usually, they aren’t as hard as we first perceive them to be.
📙 If you’re a fan of my day job (working at Money with Katie), Katie’s first book comes out June 10th and we’re hosting a launch party in New York City. Come join us (and we can hang!).
👀 I’m nosy so I loved this feature, “Summer Travel Plans from the Coolest People I Know” from
.🥰 The kind folks at Riley Home sent me this linen throw, and it is perfect for home or travel—it’s so soft, matches everything, and is small enough to pack as an additional layer. Thank you,
and team—Sogole’s newsletter about fashion is also incredible.🌲 Chattanooga is North America’s first “National Park City”—time to add it to the list for fall!
🦟 If you get bitten up like I do in the warmer months, grab these relief patches and thank me later. (Or repel them from the get go with these wipes.)
Once again, I’m so glad to have this little community—one where I can work with writers, collaborate with brands I actually admire (read: not what’s shilled by the highest influencer rate), and hear from travelers around the globe. What a gift.
—Henah x
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Florence is such a special place! I've had fab solo trips there, including to a writer's retreat. Glad Jenna had such an inspiring experience!