I’ve always had a problem with commitment.

Whether it be to people, places, or plans, I struggle with the idea of being tied down by anything — a struggle that very much translates into the way I travel.

Sure, I’ll read up on the place I intend to visit — researching for a trip is half the fun — but the idea of actually committing to a specific itinerary repulses me. What if something cooler and less touristy comes up? What if my prearranged plans prevent things from organically falling into place? What if I meet a beautiful Brazilian surf instructor who steals my heart during an evening of dancing on the beach — only to be forced to say goodbye the very next day due to an outbound flight scheduled months in advance.

These. Things. Happen.

And these things are a few of the reasons I am so hesitant to devote myself to any one plan.

However, things also happen when you DON’T have any plans — things that are less than ideal.

For example, there’s the possibility that the bus you were hoping to catch, but didn’t book tickets for, is full by the time you get to the station. That the plane ticket you refused to buy in advance has now tripled in price.

OR that after consciously making the decision not to book accommodation for the night you arrive in a city at 1am, you’ll end up walking around in the dark for 3 hours with everything you own on your back, only to be repeatedly turned away form every hostel you seek out until you’re eventually forced to sleep on a patch of grass outside of a church amongst other homeless people.

And inhale.

I know these things happen, because that last one happened to me.

A Late Arrival in Florence

During university, I spent my junior year studying abroad in Florence. Those 8 months completely changed my life, inspiring my love of travel and acting as the fodder for this blog. On the day of my departure, I sobbed until my eyes swelled shut and made a promise to myself that I would return.

On the Triangle Bridge in front of Ponte Vecchio on my last morning in Firenze. April, 2010.

Many others vowed the same thing; I heard a number of my classmates say, “I’ll come back someday.” Yet, that didn’t seem good enough. How could I offer such a vague promise to a city that I loved so dear? I knew I had to return sooner than “someday” — and so I did.

17 months after saying adieu, and just 4 months after graduating from college, I stepped foot in Florence once again.

But I’d changed a lot since first leaving. My 4 months of backpacking through Europe had made me more adventurous and had increased my aversion to pre-planned itineraries. Mia and I flew in from Ireland, a country where we hitch-hiked our way around a majority of the time, and never hesitated to pitch Tent in some farmers’ field to save a buck.

Thus, I arrived in Florence doting a very care-free, almost cocky, attitude that rejected all and any plans.

Including, but not limited to, plans for where we would sleep the night we arrived, all the while knowing full well that our bus wouldn’t arrive into the city until 1am.

If you’ve been scouring Urban Dictionary for the definition of a “tool,” there you go.

When our bus pulled into the station at a quarter past one, we immediately hopped off and ran towards the Duomo. The thought of seeking out a hostel faintly passed through my mind, but I ignored it. I was in Florence! Surely something would work out. Something exciting and fun, and that would’ve been otherwise impossible had I made any plans.

We stood on the steps of the Duomo for a while, gazing up at its vastness and reminiscing about the many a memorable moments had in that spot. Mia asked if we should check into a hostel so we could drop off our bags before exploring more. I shook my head. We still had to go to Santa Croce! And Ponte Vecchio! And sit in the Loggia and wait for something really amazing to happen — and God forbid we void the opportunity for such amazingness by settling into a hostel.

We kept walking.

The city was still relatively lively considering the hour. Many young Italians lined the streets, drinking beer and kissing in corners. We walked through Piazza Santa Croce, and again I was flooded by a sea of memories. My favorite pub, The William, was on the corner, and we peered inside to find a crowd of people standing around the bar.

For the first time I wished that we had booked into a hostel. I wanted to go inside and have a drink, but it didn’t seem possible with our big backpacks in tow. Next time, said Mia. So we carried on towards the bridge.

Ponte Vecchio was quieter than the rest of the city. The air was cool and there were few people around. Again a sense of happiness and familiarity washed over me, but with that warmth came languor. I was tired. It was well after 2, and the thrill of being in Florence with no plan had begun to wear off.

We started trying to find a place to stay. Neither of us had phones with internet access, nor did we carry a guidebook of any sort, so we were forced to rely on our eyes alone as we walked through the city in search of a hostel. I had been so confident about my knowledge of the city, but I quickly realized that I had no idea where any of the hostels were as I had never needed one — and let me tell you now, hostels in Florence are not well-marked.

We managed to find a handful, but no one answered. The few that did told us that it was too late, they had no room, or simply, to just go away. One place offered us a bed for 180 euros. It was at this point that I began to feel discouraged.

My back ached; my legs were exhausted. All I wanted was to lay down. Suddenly, being completely free felt more like a burden than a blessing.

We kept walking.

It was now well after 3am. The streets were completely barren. We once again strolled through Piazza Santa Croce, except this time there weren’t any teenagers sitting around. The only things that remained were empty bottles and plastic cups, friendly reminders that everyone else had gone home for the night whilst we remained homeless.

I became agitated. I wanted to go to bed. I was tired of playing the role of the hippy backpacker who was too cool to have organized a place to sleep for the night. I had been trying too hard to be the free-spirited wanderer and now it was biting me in the ass.

I tried to make myself feel better.

This will make a great story, I thought to myself. This is the kind of wild, stupid shit that you’re supposed to do when you’re traveling. Remember that one time when we slept on a cement bench outside the Uffizi? Har-dee-har-har. YOLO! Yeah, shoot me in the foot. No, make it the kneecap.

We kept walking.

Then suddenly Mia had an idea. We could go see the vespers chant at 5am at San Minato, the church situated just beyond Piazza Michelangelo! This way we’d at least be inside for a while, and from up there we’d have a beautiful view of the city of Florence. Plus, perhaps the nice nuns would take pity on us and let us take a little nap.

Brilliant! I was instantly rejuvenated. The possibility of having a plan (and maybe even a bed!) gave me a sense of hope, despite the fact that we had a long walk ahead of us.

We trudged on. Getting up the hill towards San Miniato zapped all my remaining energy. I was sweating yet cold at the same time. However, none of that mattered as we were now just a few meters from the entrance of the church and the welcoming arms of the kind folks who resided within.

But when we got to the stairs, we noticed that the gate was locked.

My heart fell.

Mia walked up to the top to read the sign: “Vespers 5pm – 6pm”

PM not AM. We were 12 hours early and officially homeless for the night.

So that’s when I sought out a grassy area near the church as our new place of residence.

Obviously it wasn’t ideal. Yet, the grass was soft and there was far less pedestrian traffic than down in the city center. We yanked out our sleeping bags, set up our backpacks as pillows, and tucked ourselves in behind a large tree whose shadow provided ample darkness.

It was a cold night. My sleep sack was thin, and thus didn’t weather very well against the coolness of the grass. I also had a hard time sleeping as one ear remained open to the slightest of sounds, afraid we’d be mugged or assaulted. At one point I thought I heard rustling noises nearby, but Mia assured me that it was all in my head. However, eventually exhaustion got the best of me and I completely dozed off.

Only to wake up to this.

Suddenly it was sunny out. Definitely past 7am. I sat up and was greeted by the most beautiful view of Florence I’ve ever seen. The city looked so magnificent blanketed in the haze of dawn. I have so much love for Florence, and finally being able to see it in all its lit glory was breathtaking. Plus, after what we’d been through the night before, I was all the more grateful to enjoy it in the daylight.

A loud noise to my right jolted my attention away from the view.

There were people sleeping next to us!

A man and a woman had also been sleeping in the shadows, just a few meters away. Their set-up was much more elaborate. They had a large tarp, which was laid out on the grass. On top of that was a pile of old blankets, one of which the woman was folding, and also a shopping cart filled with clothing.

It was apparent that this wasn’t their first time sleeping out here. Most likely, this couple spent every night cuddled up on this grassy patch of land sandwiched between the church and a road. They saw me staring, and then they smiled and waved.

And that’s when it hit me.

There are people who spend every single night in search of a place to sleep.

Obviously, I knew this beforehand, but until that moment I don’t think I’d ever realized what that really meant. I felt shallow and spoiled. I felt like I had learned some big life lessons in the last 8 hours, and was keen to start reanalyzing my life.

But right then was not the time to do it. At that moment, the only thing that needed to be done was to smile and wave back to my friendly neighbors. And so I did.