Day Trip from Milan: Our Portofino Disaster

“Take a day trip from Milan to Portofino,” they said. “It will be easy,” they said. Wrong. If anyone told you the train systems in Italy were easy to operate, they were dead wrong. You probably shouldn’t have even trusted that person for a gelato recommendation.

It started as a hopeful day. At least for me. Poor Xavier. He was tired, and I was dragging him to another all-day sightseeing activity on his Sunday that he likely already knew would not go as planned.

We boarded the train at Milano Centrale at 9am, set to arrive in Genova at 11. From there, we had about two hours before our ferry to Portofino. Because we were doing this as a day trip, unless we wanted to leave at 5am, this was our only option. A 90 minute ferry each way, with only 70 minutes in Portofino.

In typical Italian fashion, our train to Genova was 30 minutes late. Not ideal, considering we already had such limited time. To make things more chaotic, a close friend of mine from high school was also living in Italy at the time and staying with family in Genova. She was planning to meet us in the town square. She was also an hour late. Not because of transportation delays. She was just always late.

By the time we arrived in Genova, it already felt like we had lived a full day, and it wasn’t even noon. Little did we know, that delayed train would end up being the least of our problems.

We sat down at a small pizza restaurant and ordered a beer and a Stracci Bianca to share, a white pizza with olive oil, salt, and the freshest stracciatella I had ever had. I still remembered the soft, stringy texture and the saltiness of the cheese.

Eventually, my very late friend arrived, and we made our way to the port to board our ferry to Portofino. We grabbed Aperol spritzes to go and brought them on board. The ferry ride would pass the seaside towns of Camogli and San Fruttuoso, neither of which we could stop at with our ticket.

The ride itself was beautiful. From the water, we could see colorful buildings stacked along the cliffs, set against the bright cerulean blue sea. San Fruttuoso looked like a postcard, with small fishing boats bobbing in the water, families under umbrellas, and the shoreline meeting clear turquoise waves.

When we arrived in Portofino, the captain spoke over the intercom. “4:50 is the departure time. You must be back at the port at 4:50.”

I looked at the clock. It was 4:00 as we pulled into the dock.

Wait, what?

The tour said we had 70 minutes. If we had to be back at 4:50, that meant we were boarding at 4:50, not leaving then. Suddenly, we only had 45 minutes in Portofino.

My friend and I split up from Xavier, who just wanted to sit at a cafe and have a beer, which in hindsight was absolutely the right call.

Instead, we rushed through the one main street in Portofino, window shopping the impossibly expensive stores. We eventually found a jewelry store that looked somewhat attainable. I bought a bracelet with Murano glass charms, and my friend found a pair of earrings.

Then we decided, for some reason, to grab gelato and take it up to Castello di San Giorgio for the view.

I checked the time. It was already 4:35.

We rushed up the stairs, me holding my melting ice cream, snapped a few quick photos, and took in the view for what felt like seconds before heading back down. The whole moment felt sped up, like we were trying to squeeze an hour into a few minutes.

By the time we got back to the port, it was already 4:50. There was a long line of people, so we assumed we were fine.

Then I realized Xavier was nowhere to be found.

I texted him, but my messages weren’t going through. His phone had likely died, which I remembered him mentioning earlier. Not ideal.

My friend and I quickly checked the cafes near the port and found him sitting by the water with a freshly poured beer in hand.

“Did you just get that?” I asked. “We’re supposed to be back at the ferry right now.”

“Oh shit,” he said, immediately flagging down his server.

All three of us sprinted back to the port and got in line. We waited. 5:00 passed. Then 5:10. The ferry still hadn’t arrived, which felt strange.

We spotted a man in a captain’s uniform nearby and asked him about the ferry to Genoa.

“Genoa? Gone. 4:50, gone. No more boats to Genoa. You take train from Santa Margherita.”

Gone.

I looked back at the long line of people, suddenly realizing none of them were waiting for our ferry. We didn’t even know what line we had been standing in. All three of us just stood there, stunned, feeling like complete idiots.

Now our only option was to take a bus to Santa Margherita, then a train to Genoa, and then another train to Milan, which we were almost certainly going to miss at this point.

Once again, we made our way up the steep cobblestone streets to the bus stop, just in time to see a bus pulling away. The next one came about 15 minutes later and was completely packed, but we squeezed on anyway.

It was late July, hot, and we were pressed shoulder to shoulder as the bus wound along narrow cliffside roads. When we finally got off in Santa Margherita, it felt like a small victory.

We had some time before our next train, and since we were right by the beach, we decided to go for a swim. At that point, we had already accepted that the day was completely off the rails.

Getting into the water ended up being the best part of the day. For a few minutes, floating in the waves, everything felt calm again.

But we still had a train to catch.

When we left the beach, we found a long line for the changing area. Waiting wasn’t an option, so we awkwardly held up towels for each other and changed as quickly as we could.

We made it to the station just in time, and somehow, the train was actually early. We got on, relieved. That’s the thing we learned about Italian trains: you have to be ready for anything.

My friend would get off in Genoa, while Xavier and I would continue on to Milan. We said goodbye to her, thinking how nice it was that her travel day was almost over.

Ours was far from it.

At the second-to-last stop before Genoa, nearly everyone got off the train. Then it just sat there. After a few minutes, we realized we were the only ones left.

We stepped off and asked someone if the train was continuing to Genoa.

“This train end. No more,” they told us.

We had gotten on the wrong train. Again.

We sat on a bench at the station, exhausted, hungry, and overwhelmed. It was close to 7pm, and the only things we had eaten all day were a slice of pizza and a gelato.

When the next train arrived, it said it went directly to Milan. I remembered my girlfriend had said even if you missed your train, you should be able to use your ticket again for another time as long as it is of equal price. 

The train was a different company, but at that point, I wasn’t thinking clearly. I just wanted to get home.

We boarded, and almost immediately, I realized something was off. This train was much nicer. Assigned seats, tables, a quiet, composed atmosphere. Everyone seemed to belong there.

And then there was us; sweaty, confused American tourists.

People were staring. A woman across from us, sitting with her husband and children, was whispering to him while looking in our direction. The conductor came by, spoke with her, and then walked toward the back of the train, where it looked like he was making a call.

I felt my face getting hot.

I leaned over to Xavier and whispered, “We made a big mistake. We need to get off at the next stop.”

It felt like forever before the train finally slowed down. As it approached the platform, we stood up before it even came to a complete stop, ready to get off as quickly as possible.

The doors opened.

And directly in front of us, standing on the platform, were two polizia officers, waiting to board the train.

For a split second, no one moved.

We were standing in the doorway. They were standing just outside. We all stared at each other.

I quietly said, “Scusi,” and we slipped past them onto the platform, trying to act as normal as possible while our hearts were pounding in our chests.

We didn’t stop walking until we were well away from the train, adrenaline still surging. If we thought the day couldn’t get more stressful, we were wrong.

We eventually found a McDonald’s in the station and sat down, completely defeated. We had avoided getting into serious trouble, but in doing so, we had once again missed another train back to Milan.

The next option was a 9:30pm train with a transfer in Voghera, getting us home close to midnight.

For that train, we double-checked everything with multiple people before boarding. Even then, we still didn’t trust it. A group of American girls boarded after us and asked if the train was going to Voghera.

“We think so,” I said. “Your guess is as good as mine.”

At that point, everyone was just hoping for the best.

The train left late, which immediately made us nervous about our already tight connection. When we finally confirmed with a conductor that we were heading to Voghera, we felt a small sense of relief, but it didn’t last long.

As the ride went on, it became clear we were going to miss our connection.

When we arrived in Voghera, we were already too late for the train to Milan. We followed the American girls, along with an Italian man and another traveler, all of us trying to figure out the next move.

The bus station was empty.

It was 11pm on a Sunday night, the streets dimly lit and quiet, except for shouting nearby that made everything feel just a little more tense.

We stood there together, refreshing apps, scanning the area, trying to figure out where this bus could possibly be.

Then one of the American girls pointed down the street. A bus was sitting at a red light in the distance.

Without even saying anything, all of us just started running. Full sprint. I remember thinking how ridiculous it all was in that moment and I burst out laughing as we were running. Here we were, with 6 other strangers from all over the world, connected by this moment of travel stress.

The light turned green, and the bus started moving. We all slowed down, thinking that was it.

Then it stopped again.

We took off running even faster, waving and yelling toward the driver.

Somehow, he saw us.

The door opened.

“Milano?” we asked, out of breath.

“Si, Milano,” he said, gesturing for us to get on.

We climbed onto the bus one by one, exhausted and relieved beyond belief. That bus driver was an absolute hero.

We collapsed into our seats toward the back, the air conditioning hitting our faces as we finally started to calm down.

As we sat there, completely drained, the Italian man who had run with us walked down the aisle, looking entirely unfazed. As he passed us, he glanced over and said, “Welcome to Italy,” before taking his seat.

We finally made it back to our Milan apartment at 1am.

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