Tensions Rise in Milan


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In 1999, a stop in  Milan on my first backpacking adventure with 3 friends, was a blend of excitement, awe, and unexpected challenges. From eagerly anticipating the San Siro stadium to struggling with accommodation without a guidebook, we experienced the highs and lows of travel. The magnificent view of the Duomo di Milano was overshadowed by the practicalities of finding a place to sleep. Group dynamics were tested as tensions flared over finances, leading to a night of wandering and adapting to unforeseen circumstances. Our journey in Milan, though testing, was a crucial part of our overall adventure, teaching us valuable lessons in adaptability, teamwork, and the beauty of embracing the unexpected.


Our conflict was more than just a squabble over finances. It was an early sign of the cracks beginning to form under the pressure of constant travel and clashing individual expectations. I didn’t realize it at the moment, but it was a foreshadowing of the challenges that lay ahead.


From Seaside Serenity to Urban Energy

After leaving the peaceful beaches of the Cinque Terre, we took the small train to Genoa. On the train, the mood was light and cheerful; we laughed and played Euchre, enjoying each other's company.

The closer we got to Milan, the more our excitement grew. We couldn’t wait to see San Siro stadium. We’d been talking about this since we conceived our trip. Everything else the city had to offer was secondary.

We had no concrete plans upon arrival, but there was a shared confidence in our ability to navigate whatever lay ahead. We were truly back on track, embracing the spontaneous spirit of our adventure.

This marked a change from the quiet Italian coast to the possibility of exciting city life. As we traveled, the beautiful Italian countryside slowly changed into the busy city of Milan. The difference was clear – we were moving from the calm seaside to the lively city known for fashion and business. Milan was waiting for us, a city where old buildings meet modern style. We were ready to explore its streets and experience all the new and exciting things it had to offer.

A Friend in Need

As the train neared Milan, I glanced at Matt. The loss of his backpack and belongings from the station locker in Rome was a stark reminder of our new reality to help Matt financially the rest of this trip. With limited funds and only the clothes on his back, the generosity of his friends became his lifeline.

With Matt’s loss still fresh in our minds, we didn’t trust the station lockers. With our backpacks securely strapped to our backs, we hopped of the train and exited Milan's central train station.

Seeking Shelter in Milan

As we stepped out into the city, our surroundings were marked by the late afternoon sun casting long shadows over the grandeur of Milan's streets. We could feel the city's energy, a blend of history and modernity. Yet, we were immediately faced with a challenge - finding affordable accommodation without a guidebook, a test of our resilience and patience.

The unfamiliar streets of Milan quickly became a maze, intensifying the stress of our quest for accommodation. The fatigue of the day weighed heavily on us as we aimlessly wandered in search of a place to rest. The fading light of dusk only added to our growing frustration. Tempers flared and patience wore thin; the adventure of exploring Milan was losing its charm to the reality of our situation. It was evident that the journey was starting to test our bonds, revealing the challenges of maintaining harmony within the group.

A Moment of Awe

Then, just like on my earlier visit here a week ago, we emerged from a side-street and found ourselves staring in awe of the Duomo di Milano - the huge cathedral of Milan. Its imposing structure dominated the skyline, its intricate details almost surreal. It still almost looked fake, like one of those 3-d puzzles but on a much grander scale.

The cathedral stood out against the city skyline, a beautiful mix of old architecture and history. Yet, even in the shadow of such beauty, our immediate concern was to find a place to stay, a reminder of the practical challenges that often accompany the wonders of travel. By this time tempers were flaring because we had been wandering around the city aimlessly and it was getting dark and we still had nowhere to sleep.

A Glimmer of Hope Before the Storm

Matt realized we needed to pause and figure out a game plan. He popped into a nearby bookstore and purchased a Let’s Go Italy guide book. Sadly it didn’t help us much in finding a place to sleep.

In a moment of clarity, Matt proposed a halt to our aimless wandering. As Mike, Zen, and I huddled to discuss our next move, Matt darted into a nearby bookstore. He emerged clutching a 'Let’s Go Italy' guidebook, his face alight with a flicker of optimism. This guidebook, he believed, would be our compass in the sprawling city. But even this attempt at finding a solution to our current dilemma couldn’t ease the growing tension, and became yet another point of contention.

As soon as they saw Matt had used the little bit of cash he had left on the guidebook, Mike and Zen demanded to be repaid, which pissed Matt off (rightly so I thought). They accused him of having more money than he’d let on since his pack got stolen, and demanded immediate repayment of the money they’d been spotting him since Rome.

Now both Mike and Zen said they wouldn’t pitch in to for the book, nor for a hostel, because Matt owed them cash, which of course he did. However since he had recently lost ALL of his stuff, I figured the guys would let him go until he got home as I ended up doing - and I had much less daily budget than anyone.

This conflict was more than just a squabble over finances. It was an early sign of the cracks beginning to form under the pressure of constant travel and clashing expectations. I didn’t realize it at the moment, but it was a foreshadowing of the challenges that lay ahead in navigating not just the streets of Milan, but the dynamics of our travel group.

Adding to mounting anger, the guidebook, our beacon in the chaos, failed to deliver. Pages filled with promises of hidden gems and cheap hostels throughout Italy, brought us no closer to a finding an available bed in Milan. Matt's initial enthusiasm faded into collective disillusionment, the guidebook transforming from a symbol of hope to one of frustration. Our predicament remained unsolved, the streets of Milan offering no respite as nightfall encroached.

Stumbling Upon a Hostel at the Eleventh Hour

Just as the four of us hit our breaking point from exhaustion, our luck finally changed. Around 11:00p, we stumbled upon a basic hostel above a local bar, which felt like a small victory after the long, frustrating search. But even as we checked in, it was clear that the day's tensions had gotten the best of us. Everyone needed some space to cool off, especially Matt and Zen, who were at each other’s throats by this point.

Realizing a change was needed, I suggested a different approach for the night. It seemed best if Matt and I stayed somewhere else, giving Zen and Mike some space and hopefully time to cool off. Everyone agreed it was a good idea. Matt and I decided we’d use a little trick I’d learned before meeting up with the others: we’d hop on a train going to a nearby town about four hours away, and sleep on the train. Then we’d wake up in the new town, switch trains to come back Milan, and sleep for another 4 hours. It wasn’t the most comfortable option, which after the day we’d had we really needed, but it would provide everyone the time they needed to cool down and would be a free night’s rest.

Shattered Expectations

With this plan all set, we told Mike we’d meet him and Zen at the train station in the morning. There was a sense of relief in the air – a welcome change from the stress of the day.

Sadly, that didn’t last long. Our departure from the hostel took an unexpected turn - literally. As Matt turned to leave the reception area of the hostel, his pack collided with a vase, shattering it as it hit the ground. “What a perfect end to an awful night,” I thought. Little did I know, it was just the beginning.

Wandering Milan After Midnight

Leaving the hostel embarrassed but luckily not having to pay for the broken vase, Matt and I headed to the nearby Metro trying to make the last night train out of Milan - 12:00a - as it was already very late. The Metro stop was closed. It had closed at 11p. Now we had to walk to the train station.

Unfortunately we arrived seven minutes after the last train for the night had departed, which meant matt and I were now stranded in Milan with nowhere to sleep. We considered going back to the hostel with our tails between our legs, but decided we should be able to find somewhere else to sleep near the train station. That was probably a mistake.

So we started walking around looking for a place to stay with the help of Matt’s new Let’s Go Italy guidebook. The place it brought us too were either closed or full, and places we found between the book’s listings were too expensive. Eventually we did find a place. However it didn’t take credit cards, and neither of us had enough cash for the night. “No problem!”, we thought, “Just head back to one of the many ATM machines we’d passed along the way to here.”.

Again, we were wrong. We must have walked at least 1.5 hours before finding an ATM that was both operational AND accepted my bank card. By this time I was so angry and hungry that I decided to break my cardinal food rule on this trip and step into a nearby open McDonald’s for American-style food. Up to this point, I’d been adamant while the my friends sought out McDonalds and Pepsi, that I would only eat local food at local places.

The night turned into an exhausting quest for a place to sleep, testing our patience and adaptability. In a moment of frustration, I broke my own rule about local dining, a small but telling concession to the pressures of the journey.

Once we got back to the hotel (not a hostel), I paid for a room to share. The man at the reception desk asked for our passports, and although we were reluctant to do so, I had read in Rick Steves’ ‘Europe Through the Back Door’ before the trip, that this was a requirement of hotels and guesthouses across Europe. So we handed them over and went off to our room. Completely exhausted and having nothing much to say, we dropped our packs to the floor, stared at the small room, and crashed down on to separate sides of the single bed in the center of it.

New Day, New Direction

The next day at the station, we woke up earlier than we would have liked to the sound of the phone ringing with our wake up call. We washed up in the bathroom down the hall from our room, and headed to the nearby train station. Mike and Zen were already there, and said they had had an awesome time last night. There had been a bar beneath the hostel and they had drank and partied there all night. Matt and I decided not to share our own misadventure, and the four of us discussed where to head next.

I suggested we head to Switzerland before going off to Paris. Mike loved the idea as he’d always wanted to see the Swiss Alps. Matt suggested Turin since we were still relatively close to the city and he had really hoped we would get a chance to visit his favorite soccer team’s (Juventus) home town. Zen and Mike agreed with him. In the end , since the original plan of this trip was for four friends to visit their favorite soccer clubs and try to see a few matches, we all decided to visit Turin visit Juventus’ Stadio dell’Alpi, before heading to Interlaken in Switzerland. We wouldn’t spend the night in Turin, so we had to rush.

Luckily we found the next train to Turin just before it was ready to depart. It was only a two hour ride from Milan to Turin.Matt was visibly excited to about to see his favorite soccer club's stadium up close and in real life. Once on the train, we laughed and played Euchre for several hours before arriving in Turin. We were back on track and having a blast. We didn't have a plan, but we were confident we'd find the stadium when we arrived.

Looking Back on Milan

Milan, with its mix of awe-inspiring sights like the Duomo and our personal misadventures, left a complex imprint on our journey. It was a reminder that travel is not just about the places we visit but also the experiences, both challenging and rewarding, that shape us. As we prepared to leave Milan, I couldn't help but feel a sense of anticipation for what lay ahead, mixed with a newfound appreciation for the unpredictable nature of our adventure.

Looking back, Milan was a test of our friendship’s endurance and unity as a group.

Lessons Learned

Since that trip, I have learned several key lessons that have since guided my travels:

  1. The Importance of a Good Guidebook: Not having a reliable guidebook in Milan was a significant oversight. A well-researched guidebook would have streamlined our search for accommodations and helped us make the most of our time in the city. Instead of aimlessly wandering in search of a place to stay, we could have enjoyed Milan's attractions more thoroughly. This experience taught me the value of preparation and having a solid reference tool at hand.
  2. The Necessity of a Plan: Arriving in Milan without a plan proved to be a mistake. When time is limited, an efficient plan is crucial to experience a place fully. Relying solely on chance may sound romantic, but it often leads to missed opportunities, as was our case with San Siro Stadium, our main reason for visiting Milan.
  3. Taking Breaks in Group Travel: Continuous togetherness, while initially appealing, can intensify stress and tension, especially in unfamiliar environments. It's important to recognize the need for personal time, even when traveling with close friends or family. Allowing for individual space and activities can prevent frustrations from escalating and preserve the overall harmony of the trip.
  4. Pre-Booking Accommodations: While spontaneous travel has its allure, it also comes with the risk of not finding suitable or affordable lodging. To avoid wasting precious time on arrival, it's wise to book accommodations in advance. This approach ensures a secure place to stay, allowing you to focus on exploring and enjoying your destination from the moment you arrive.


In 1999 on a stop in Milan, my group of friends and I faced the challenges of finding accommodation and managing group dynamics. Our awe at the Duomo di Milano was juxtaposed with the practical struggles of travel. Financial tensions, a quest for a bed, and adapting to unplanned situations defined our Milan experience, teaching us resilience and the importance of embracing the unexpected.

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