Arriving in Palermo: Beginning Our Three Month Stay in Sicily

A story about how our winter in Sicily began.

One night my husband Matt and I were having a conversation about how winters in Montreal are literally the worst. One of us said, “what if we just ran away?” and then we both looked at each other and said, “wait… what if we actually did?” We thought about where to go and eventually settled on Palermo, Sicily. Why? It is warmer than home in winter, there is no snow, it is genuinely affordable, and honestly, why not?

We talked through what that would look like in practice and it seemed doable. We could work remotely, stay in Italy for the maximum time allowed for Canadians and skip winter entirely. That sounds easy to say out loud, but the logistics behind every step were a lot. This was not just booking plane tickets.

Leaving Montreal behind and starting the journey that would take us to Palermo, Sicily.

I was terrified. I had never been away from home for that long or that far. The anxious overthinking came fast. What if something happened. What if we regretted it. What if everything went wrong. I had to stop myself.

There was always going to be a reason not to go and everyone around us thinking we were a little crazy did not help. With a lot of effort, I tuned that out. Step by step, we started planning. After an enormous amount of research covering neighborhoods, traveling with pets, travel insurance and more, we finally had our adventure mapped out.

Travel champ: Our pug Bailey in her travel backpack ready for an adventure.

Our flights were booked for Christmas Day. We were really going. Passports sorted for our dog and cat, three months of medication stocked and one suitcase each.

Before heading to Palermo to settle into our new temporary home, we made a few detours. First, a few days in Paris, but more on that in another post. Matt had one thing on his list. Attending the official Italian New Year’s Eve concert in Reggio Calabria. We spent a few days there and with most things closed for the holidays, it was a pretty relaxed stretch of time.

“Arena dello Stretto” View of the Reggio Calabria boardwalk and monument by the water in Southern Italy before our trip to Palermo, Sicily.

The concert was something else. For someone who does not love crowds and gets anxiety, I do not recommend diving straight into the depth of the crowd. Matt, being the more adventurous one, went straight in. Since we had our dog with us, I found a spot further from the stage where I could still see everything. It was a warm night, Bailey tucked into her backpack wearing some homemade earmuffs, (it was actually two pairs of the thickest socks I had wrapped around her head) totally unbothered, while I watched the show. The vendors got busy and it took a while to get food and drinks, but that is just how large concerts go.

Rai 1’s L’anno che verrà Capodanno. Please excuse the blurry photo. This was Matt’s view and he was definitely dancing.

What was truly a beautiful scene was watching the entire city come together. Crowds filling the streets, people hanging out of every window of the buildings in the piazza, the lights, the music, the fireworks. Matt hopped in and out of the crowd to check on us, and when midnight came, we counted down together. Buon Anno!

Now it was time to take the train from Reggio Calabria to Palermo. Did you know the train gets put on a ferry to cross the strait? We were trying not to look too shocked since it was totally natural and routine for the locals who were unfazed.

They split the train in two and, please, make sure you are in the correct half because we were not. Apparently, the trains stay split, and both halves go to different destinations. Once the ferry left the dock, it was clear people typically head up to the deck for the beautiful view of Reggio Calabria on one side and Messina on the other.

Crossing the Strait of Messina on a train – on a ferry. One of two places in the world this is actually done.

The whole crossing takes about twenty minutes, so once we rushed with all our belongings from the wrong half to the right one, we did manage to catch the view. It was worth it.

Back on land and settled into our seats, we were finally on our way to Palermo for a five-hour train ride. I have to say, it was genuinely comfortable. We booked first class on the Trenitalia website, which was not much more expensive at all. We ate, drank, talked, stretched our legs. The espresso on board was not bad at all.

Arriving in Palermo

We rented an apartment using Airbnb, it was about twenty minutes (by public transport) from the city center, and our host was kind enough to send a driver to the train station to pick us up. Picture this. A brand-new city at eight at night, pitch dark, with your dog, your cat, everything you packed for three months and home very far away. It was a lot.

Exterior view of the Palermo Cathedral in Sicily, a major landmark near the area where we stayed.

A ten-minute drive later, we arrived at the apartment and met our host. Getting out of the car with all our bags and finally heading up was such a relief. Being on the fourth floor, I was grateful to spot an elevator, though it was very old school. A single door opening to reveal double swing doors that had to manually be held closed for it to move. It fit two people, so we made a couple of trips.

Our host gave us a tour of what I can only describe as Nonna’s place, straight out of the 1980s. Classic Italian decorative tiles, chunky baroque furniture, and even a large grandfather clock. The kitchen was more modern, with a gas stove and the typical washing machine tucked next to the sink.

Our host brought us these amazing cannoli from a local bakery just because.

On the table waiting for us: fresh bread from the bakery, cookies, and drinks. She had left it all out for us. We were so grateful. After a walkthrough of how everything worked, we said goodnight and collapsed into bed, exhausted from the long travel day and laughing about nearly ending up in Syracuse on the wrong half of a train.

Coffee and a New View

I woke up the next morning to the brightest sunshine I think I have ever seen. I went to adjust the shutters and my mouth dropped. Mountains, golden light, and the street coming to life below. The shutters were being stubborn and Matt was still asleep, so I figured I would sort those later and headed to the kitchen for coffee.

A caffe latte and a cornetto. Italians love a pastry for breakfast.

I tried to remember what our host had shown us about the cialde machine, a pod-based espresso maker popular in Italian homes. It was the best homemade espresso I have ever had. I genuinely considered whether I could fit the machine in my luggage on the way home. I took my coffee out to the balcony, sat down and stared at what was going to be my view for the next three months.

Exploring Palermo Cathedral on our first days in Sicily during our long winter stay.

Matt and Bailey eventually surfaced and came to join me. Bailey gave us the look that meant it was time for her morning walk. We were too excited to unpack, so we got ready, took the elevator down, stepped out onto the street and started exploring the neighborhood.

Here’s Bailey in her earmuffs. 😊

More to come.