Booked the Wrong Hostel in Florence. Turned Into A Great Mistake.
Lost in Florence with no phone, no map, and no plan. Yet somehow it was perfect.
I stood on the platform below the dim yellow glow of a flickering lightbulb at a train station in Amsterdam. It was the 3am witching hour, the time that means early for some, late for others. Around me, clusters of still-drunk twenty-somethings in smeared makeup and clubbing outfits were still living yesterday. For me, today was already a new day and I was heading to the airport for a 5:30am flight to Pisa, Italy.
Nothing was planned. Yesterday, I’d decided I’d seen enough of Amsterdam and picked the cheapest flight out… Pisa. On the way to the airport, I read online that Pisa doesn’t have much beyond the leaning tower, so I booked a train from Pisa straight to Firenze (Florence), the city I’d read about in Leonardo Da Vinci’s biography. I was already imagining myself waking up between walls of art and walks through history.
All that was left was for me to book my hostel. In my spare time sitting at the gate before boarding my flight, I went on HostelWorld.com, sorted by price and rating, and booked the first hostel on the list without a second glance.
Upon arriving in Pisa, I had a couple of hours to kill before my train left for Firenze. While my intention was to see the leaning tower, I learned it was an hour’s walk, and with the heat of the day and my big backpack, I decided to skip it and instead retreat into an espresso bar with the locals.
When my train arrived in Firenze, the first thing I did was take out Google Maps and route it to my hostel. I wanted to rid myself of my heavy backpacks so that I could be free to roam the streets at my leisure. Except when I routed my GPS to the hostel, it showed two buses and another hour and a half of travel time to a place in the middle of an olive grove.
The Mistake
Sweat beaded on my forehead as I stood on a bustling corner with the weight of my backpack feeling like a load of bricks. My data was running low on my phone, but I was being stingy with it and didn’t want to open my browser, but I risked it to double check where my hostel address was. Turns out Google Maps wasn’t wrong. I’d booked a hostel1 that wasn’t even in Firenze itself. The day was far from over.
My visions of sipping an Aperol spritz that evening while watching the sun go down by Santa Maria del Fiore, quickly disappeared. Instead, I stood on a corner for an hour waiting to get on a bus only to find out they didn’t take cash and I had to go somewhere else to get a ticket. An hour later, I was able to get on a bus only to have it drop me off at the end of the line in another town. From there I had to catch bus 33. It arrived within 5 minutes and I was overjoyed at my luck. Once on the second bus, I saw it started going in the opposite direction from the hostel. In a mix of Italian and Spanish, I asked the bus driver and he said this was 33A, and I was supposed to be on 33B. Crap.
I got off on the next stop, the middle of a ghost town on the outskirts of Florence. I opened Google Maps yet again, to check where I was and where the other bus was, when suddenly my internet cut out. My SIM card, depleted.
So here I was, on a Sunday, with all stores and restaurants around me boarded up closed, no people in sight, with a heavy backpack, no way to make any calls or use the Internet. On top of that, the sky churned with humidity and turned a nasty gray.
It was one of the few instances in my life where I was completely flabbergasted. In a world so connected by devices, where we share where we are all the time and where others can see our location … for the first time, I was completely disconnected. No one knew where I was. I didn’t even know where I was.
With an impending storm, people must have gone inside to hide because no one even passed me on the street. No people, no cars, no bus. Nothing. I took my backpack off and sat on the curb, in surrender.
Like A Rolling Stone
My mind wandered back to a fable I read in Walter Isaacson’s Leonardo Da Vinci biography:
“A stone of a good size, recently uncovered by rainwater, lay in an elevated spot where a pleasant grove above a stony road. Surrounded by herbs that were adorned by various flowers of different colors, the stone viewed the great number of stones lying in the road below it. It conceived a desire to roll down, and said to itself: “What am I doing here among these herbs? I want to live in the company of my fellow stones.” So letting itself roll down, it finished its tumbling course among the companions it desired.
But after a while it began to suffer continual distress under the wagon of wheels, the hoofs of iron-shod horses, and the feet of travelers. Some of them turned it, and others trampled it. At times it raised itself up a little, all covered with mud or animal dung, and in vain looked back at the place it had left behind, a place of solitary and tranquil peace. This happens to those who leave the solitary and contemplative life and choose to live in cities among people full of countless evils.”
Is that what I have done for myself? How many days had I fantasized about a leisurely trip to Italy sipping wine and eating pizza and looking at art? But now that I was here, I was wishing I could be at home in the comfort of my bed, curled up with a book. Instead, I’m out here, a broke backpacker in the middle of nowhere in Italy, stranded without a phone and no shelter with a storm on the way. Is this what I get for choosing the path of adventure?
Thirty minutes later, a savior arrived.
Saved By A Stranger
As I sat there thinking about stones, a flicker of movement caught my eye. The first human I saw after an hour of sitting there, appeared in front of me in the shape of a woman with an umbrella in hand walking toward the bus stop. Relieved, I shot up and ran to her.
Thank goodness I’d paid some attention in Italian class back in high school. Back then I never would have thought it would save me in a situation where even Google Translate had fallen short. In elementary Italian, I managed to communicate my situation to her and she let me borrow her phone to check the location of the hostel. She said she would wait with me for the bus, because she was taking the same one. Sometimes, another stone crosses paths with yours and saves you.
Once on the bus, we used her Google Translate to have a long pleasant conversation. She said she admired my energy and spirit of traveling and was glad we crossed paths. Before she got off the bus, she told me to take the bus all the way to the end of the line. That it would leave me in a parking lot and from there I could walk 20 minutes to the hostel. I said ciao to this kind stranger and she got off the bus with her umbrella and disappeared in the rain.
The rest was exactly as she said. The bus route ended in a very empty parking lot on the edge of a hill surrounded by a whole lot of emptiness. There was no mistaking the road I needed to take and continue to the hostel. But what the woman left out was that it was a complete steep gradient uphill. Only 20 minutes, I told myself.
Fat raindrops fell out of the sky. I clutched my laptop backpack to my chest, and tightened the straps on my big backpack on my shoulders. It was hot and I was starting to get drenched. It would have taken 20 minutes had it been flat, but turns out it was a one-mile climb up a mountain and it felt harder than any of my previous endeavors. Suddenly it felt harder than the marathon I ran, than the half Ironman, than the 10-mile swim. I looked down at my arms which were still bruised from having trained in Shaolin Kung Fu a few days earlier. Each step up the hill felt like my legs were carrying bricks of cement.
At one point I stopped and looked around. Here I was, in Italy. In Tuscany surrounded by a grove of olive trees, with no people or cars in sight. The sky had stopped crying and I could hear the birds. I reminded myself that if I could do all those things, I could get up this damn hill. My legs kept moving until eventually after what felt like hours, I caught sight of what could only be the hostel balanced on the tip of the hill with a couple of cypress trees guarding the entrance.
The Monastery
It felt straight out of a Harry Potter book. Turns out the hostel was this enchanted ancient monastery right on the Franceso d’Assisi pilgrimage trail. It was built in 1214 to provide food and housing for pilgrims and travelers, and later on converted into a monastery for cloistered nuns. Nowadays, it is restored with original features of coffered ceilings and wooden box beds. The beautiful brick plastered building seemed to glow like I had reached the pot at the end of the rainbow. It seemed for those brave (or crazy) enough to endure the challenge of getting here, a reward awaited.
It was a comical scene. One I thought was unique to me but quickly learned was repeated multiple times a day: A backpacker arrives, huffing and puffing, drenched in a mix of rain and sweat, staggers into the dark lobby of a former monastery lit by candles. “Wow, that was a crazy hill.” As the main greeting to the receptionist, who then handed the traveler a cold glass of water with an all-knowing smile.
It wasn’t just my story. Within 15 minutes of playing that scene out myself, I witnessed several other travelers that same afternoon, repeat the scene over and over.
Turns out most of us hadn’t read the details of the Hostel World page sharing about the hostel’s location and the odyssey to reach it. But it was one of the most enchanting places I’ve ever stayed at. Not just because it’s a trek to get there, but because what united us travelers was the challenge of getting there.
Before I came to terms with my situation, however, I did try to change it. I was frustrated I was staying so far away from the city center. I’d come all this way to get to enjoy Florence and see its museums, and now I was staying an hour and a half away. Completely isolated from the main attractions. I went back on Hostel World and tried to look for a hostel in the city center. I cursed my luck when I saw they were all sold out.
Because the hostel was far away from anything else, the only thing to do was talk with the fellow hostel guests. We sat on the terrace overlooking the city in the distance and the receptionist brought out bright orange glasses of Aperol spritz. We saw the most magnificent sunset perched from this monastery on the side of the hill and could see Santa Maria’s duomo in the distance. When it was dark, we were all summoned into the main hall, straight out of Hogwarts.
Under the glow of a real candlelight chandelier, was one long wooden table fit for thirty people. Glasses of red wine, bread with butter, and dishes of pasta awaited us. We ate together in this room lit up by stories of travelers from all over the world who found themselves together in this strange place, just by chance. This scene repeated itself every night. Each evening there was a different type of pasta, different type of wine, and different person to share a meal with.
We stayed up so late that night chatting with the other guests until even the fireflies went to bed. I enjoyed my first day there so much, that I extended for five more days. That place was special and felt like we were transported back to medieval times under candles, through dark hallways, and in whispered conversations with travelers from far away places each on their own quests.
The Pilgrimage
The following morning after having cake and coffee for breakfast on the terrace, my new friends and I ventured down to the city together. We spent the day wandering Florence, eating gelato and exploring museums. But we also encountered the masses of tourists and long lines for everything. When it was time to go back, we were relieved we were heading to our sanctuary.
This time all of us knew the correct bus to get on and were aware of the long walk up to the hostel. In consensus, however, we decided to try our luck with hitchhiking from where the bus dropped us off, up to the hostel.
It was my first time hitchhiking and I was nervous as I stuck my thumb out on the road. Luckily, the first car that passed, stopped for us. As we peeked through the driver side window, we saw there was no one there. On the passenger side, however, at the wheel was our British friend who was staying at the hostel. With big smiles at the coincidence, we hopped in his English van without hesitation.
The next day, instead of going back to the city, a group of us took a stroll from the hostel through the Franceso d’Assisi trail to a neighboring village. Here, we found the best dark oily espresso I’ve ever had along with a big lunch and fluffy creamy tiramisu to satisfy our appetite.
For the days that followed, guests came and went, friends said goodbye while others arrived. I didn’t go back down to Florence, rather enjoyed our days in the monastery’s garden deep in conversation with guests or the receptionist or sitting with a good book and glass of wine.
Sometimes when I feel I want to rush through life by opting for the shortcut of conveniences, I am reminded of this story: That the good parts are the ones that come in the shape of challenges, strangers, and unexpected twists. The winding road with the hills is always worth the climb.
(Video above is my reaction when I saw the hostel getting toward the top of the hill)
Thanks for reading this story. If you enjoyed it, please give it a like, leave a comment or share with a friend. Here’s to more stories of travel and lessons weaved within the unexpected.
Antico Spedale Bigallo. “History.” Accessed May 27, 2026. https://www.anticospedalebigallo.it/eng/history/.
Isaacson, Walter. Leonardo da Vinci. New York: Simon & Schuster, 2017.
Our most memorable stories often begin with a bizarre plan and almost no notice at all.
The hostel looked so fun and vintage, nothing like the road that led you there. Maybe someday, when I find myself around and know of this deserted hostel hidden in the mountains, far away from the crowds, I’ll remember this blog and smile, who knows!!
Oh man, I've been there (well, not to that specific monastery hostel outside Florence, but to the place where you accidentally book a room somewhere far from where you intended and it ends up being magical).
I see it as a reminder that sometimes you're supposed to end up somewhere different from where you think you need to be.