The Inspiration Behind My Sicilian Adventure
After a two-week solo journey through Sicily in winter, I finally understood the island’s irresistible pull. Even under cloudy skies and quiet streets, Sicily shimmered with history, grit, and soul.
So what led me here?
I trace it back to the silver screen. The poignant masterpiece Cinema Paradiso, directed by Giuseppe Tornatore and filmed across Sicily and mainland Italy, first sparked my fascination. Then came The Godfather, Francis Ford Coppola’s legendary crime saga inspired by Mario Puzo’s novel, which cemented my longing to explore this captivating place.
But more than cinematic nostalgia, I was looking for a destination that felt rich in culture and welcoming in the colder months. I’d spent the previous winter in Portugal and loved the off-season calm.
I’d always assumed Sicily was best enjoyed in the sunny summer months—lemons on trees, turquoise water, that classic Mediterranean glow. But something about visiting in winter felt like it would show me a different side.
Sicily offered a similar southern charm—without the crowds, but full of life.
In this post, I’ll share how I planned my trip, where I went, and why Sicily surprised me at every turn—from missed train stops and winter fireworks to quiet cathedrals that left me speechless. Whether you’re mapping out your own Sicilian adventure or just dreaming of one, I hope this story helps you get there.
First Impressions of Sicily
Sicily is Italy’s largest island and the biggest in the Mediterranean, but it feels like its own country entirely. Shaped by a layered past of Greek temples, Roman roads, Arab domes, and Norman mosaics, it’s a crossroads of civilizations—and moods.
The landscapes alone are staggering: volcanic slopes dusted with snow, lemon groves and cactus-lined hills, crumbling seaside towns. You’ll smell citrus in the air and woodsmoke in the streets. Even in winter, it holds a kind of golden glow.
My own arrival was anything but smooth, but it was memorable. After three days in Rome, I boarded the overnight sleeper train to Sicily—a ten-hour ride that literally sailed across the sea. Around dawn, the entire train rolled onto a ferry to cross the Strait of Messina, one of the most surreal travel moments I’ve ever experienced.
Of course, I then missed my stop in Taormina, still groggy from the overnight journey and not yet fluent in Trenitalia timetables. I got off at the next station, retraced my steps, and chalked it up to Sicilian initiation. Welcome to the island—where things may not go as planned, but they’ll still make a good story.
Where I Went: My Two-Week Sicily Route
Planning a two-week solo trip through Sicily in winter meant striking a balance—between seeing the island’s most iconic sights and leaving room for spontaneity, slow mornings, and Sicilian surprises.
I focused on four main bases, with day trips branching out from each:
- 1 night in Taormina
Hilltop charm, Greek ruins, cinematic views, and a brief but beautiful introduction to the island
→ Read: Taormina in Winter: A Solo Traveler’s Peaceful Escape - 5 nights in Catania
Lava-stone cityscape, New Year’s chaos, street markets, and a base for Etna and day trips
→ Read: New Year in Catania – My Winter Trip to Sicily’s Black City - 4 nights in Ortigia
Baroque facades, stormy skies, endless charm, and the best place to get lost
→ Read: Why I Fell in Love with Ortigia, Sicily – A Solo Travel Guide & Story - 4 nights in Palermo
Grit, grandeur, rainy streets, pistachio cream, and a surprising final chapter
→ Read: Winter in Palermo – A Travel Story of Rain and Resilience
Along the way, I squeezed in unforgettable side trips to places like Savoca, Mount Etna, Cefalù, and the Valley of the Temples. Each one added a different color to the Sicilian palette.
Planning and Navigating Sicily
I’ll admit it—I underestimated Sicily.
On the map, it didn’t seem that big. But Sicily spans 25,711 km² (for context, Singapore is just 734.3 km²). My fantasy of zipping across the island like I did in Portugal quickly met reality: long distances, limited connections, and public transport that dances to its own rhythm—especially in winter.
Before the trip, I fell into a bit of a planning spiral. I read forum threads filled with travel horror stories—buses that never arrived, routes that vanished mid-journey, confused tourists stranded at empty stops. On top of that, there were whispers that some towns more or less shut down in the off-season, with restaurants closed, erratic opening hours, and streets that felt like movie sets after the crew had packed up. Sicily, it seemed, was a place where timetables were more suggestion than fact. I began to wonder if I’d spend most of the trip just waiting.
So I planned meticulously. I spent months mapping everything out. I used Google Maps to pin the places I wanted to visit, plotted routes with Rome2Rio, and tried to download the Trenitalia app, which stubbornly refused to work on my phone. Thankfully, I found Trenit!, which became my go-to app for real-time train schedules and platform info.
I also started brushing up on my Italian with Duolingo—months in advance. I didn’t expect to become fluent, but I wanted to at least be able to read a sign, order a coffee, or ask for directions. The basics went a long way, even if I mangled the pronunciation now and then.
And then there were the accommodations.
How I Chose My Accommodations (a.k.a. Proof I Am Very Thorough)
Some might call it obsessive. I call it strategic.
Choosing where to stay became a kind of side project in itself. I wasn’t just looking for a bed—I was checking which direction the balconies faced, making sure I had a private, unobstructed view of the sunrise or sunset. In Catania, I was determined to find a place with a direct line of sight to the Duomo for the New Year’s Eve fireworks. I even tried to research where exactly the fireworks would be launched from.
Spoiler: completely pointless.
If you’re expecting a ten-minute choreographed fireworks dance like the ones in Singapore or Bangkok—don’t. The official display at the Duomo lasted maybe a minute. It felt more like someone turned on a showerhead of sparks, pointed it upwards, and said, “Buon anno!” before it fizzled out.
But that didn’t matter—because fireworks were going off everywhere. From balconies, back alleys, rooftops—people lighting flares overhead and throwing firecrackers with no warning. It was loud, chaotic, kind of lawless… and absolutely unforgettable. (More on that in my Catania post).
I also made sure that every place I booked was walking distance from the city centre or close to key landmarks. I’d time how long it would take to walk from the train station to the front door. But here’s the thing: a 20-minute walk in Italy is not the same as a 20-minute walk in Singapore. Back home, it’s a breeze. In Sicily? It felt like a desert pilgrimage with cobblestones, hills, and a suitcase that develops sentience and resistance with every step.
And because I was travelling light—or so I told myself (my bag still required core strength to lift)—I filtered for washer/dryer options. Turns out, Italians are dryer-agnostic. Everything hangs out to dry, even in the dead of winter. I had no idea cold air could actually dry clothes, but the low humidity worked its quiet magic.
If a washing machine wasn’t available, I’d hunt down the nearest laundromat. I also preferred places with a kitchen, especially in Catania, where I predicted many restaurants would shut for New Year’s and I’d need to fend for myself with grocery store staples.
After all that splurging on carefully curated private stays in the earlier cities, I did a full pivot by the time I reached my final stop: Palermo. There, I booked a room in someone’s home. But it still had a terrace. And a dog. So… priorities.
What I Wanted to See (and Feel)
When I first started planning, I didn’t even know where to begin—other than knowing I wanted to see the places I’d glimpsed in the movies. The ones that had first planted the seed: Cinema Paradiso, The Godfather—those lingering shots of sun-drenched towns and crumbling piazzas.
But once I really started looking into it, Sicily felt massive, layered, and a little bit mysterious. Every guidebook and forum had a different opinion on what was “essential”—and it all started to blur.
Thankfully, I had help. A Sicilian friend sent me a personal list of places I had to see—spanning both the east and west coasts. That list became my anchor. I didn’t follow it to the letter, but it gave me a real sense of the island’s range. From there, I started ticking off what spoke to me.
Of course, in typical fashion, I was ambitious. I wanted to fit it all in. But once I realised the sheer size of the island—and how much time I’d spend in transit—I had to humble myself. I scaled back. I chose slower travel. I picked places based on what I wanted to feel, not just what I felt obligated to see.
I’ve never been the type to visit a place just for the “points of interest.” I’m not much of a history buff. I don’t do museums for fun (though I did go to a few, thanks to ticket bundles). I don’t like seeing things just for the sake of saying I’ve seen them. FOMO doesn’t work on me.
But I am curious. I love wandering. I love old buildings. I love grit. I love details that make my camera pause and my brain wander. I trawled the internet for offbeat spots—back alleys, forgotten architecture, anything stained by time. Art Nouveau? Check. Cracked tiles? Check. Rust and patina and iron balconies clinging to crumbling facades? Check.
And then came the churches.
After Rome, I didn’t think I needed to see another one. But Sicilian churches—especially in Palermo—stunned me. Some of them were the most beautiful I had ever seen.
Sorry, Sistine Chapel. The Palatine Chapel beat you on this one.
I was transfixed—by the mosaics, by the scale, by the layers of cultural influence. In those quiet spaces, my mind ran wild. Who were these artisans who painted the ceilings, carved the columns, shaped the cornices—(is that the right word? Mouldings?)—and pieced together all those floor-to-ceiling mosaics? How did they get that gold leaf to glint just so? How did all of this survive?
Baroque never really moved me in art school. But in Palermo, I couldn’t look away.
Even alone, I was never bored. There was always something to marvel at. A question to ask. A detail to follow down some mental rabbit hole. I know some of those questions could’ve been answered if I’d joined a private guided tour—but I didn’t want to be slowed down. I didn’t want to be kept on a clock either. I liked wandering at my own pace, letting curiosity lead, even if it meant walking past history I didn’t fully understand. The not-knowing became part of the experience.
I had originally hoped to visit some of Sicily’s modern art museums too—something I try to do in every country I visit. But somehow, I never made it to any of them. Not because I didn’t want to, but because I didn’t need to. I more or less had an idea of what I wanted to see, but aside from a few day trips, I didn’t book anything in advance. I let my legs take me wherever they wanted. I let my mood, the light, the smells of food in the air guide me.
And maybe that’s why Sicily felt so special. Because for once, I wasn’t trying to conquer it—I let it unfold around me.
I didn’t plan every step. I just let Sicily lead.
And it did—beautifully.
Why I Travel in December & January
It started out as a scheduling thing—my work naturally slows down at the end of the year, so I began using that window to take longer trips. But over time, it became something more. Now, I look forward to it all year. It’s the thing that keeps me going when work gets overwhelming or life feels a little too repetitive. Honestly, it’s become a non-negotiable. If I don’t leave the country at least once a year, I’ll probably shrivel up inside like a forgotten raisin on a windowsill.
There’s also the practical side. Traveling in the off-season means cheaper flights, more affordable accommodation, and fewer crowds—which is perfect if you’re budget-conscious or just allergic to queuing. You may need to trade a bit of sun for a jacket, but in return, you get space to breathe.
No squeezing through crowds. No fighting for the best view. No dodging selfie sticks. Just you, the place, and whatever it feels like showing you that day. I love seeing a destination in its quiet season. It feels more real. No performance, no show—just life as it is.
Of course, winter travel in Sicily has its quirks. Some restaurants and shops shut down for the holidays, and Google is notoriously unreliable in Italy—especially when it comes to opening hours. I’d show up to places clearly marked “open” only to find the shutters down and a handwritten sign taped to the door, probably saying something poetic in Italian like “torniamo quando ci va” (we’ll be back when we feel like it).
And while I’m not one for countdown parties, I did notice that Catania had set up a big concert stage in the piazza for New Year’s Eve, with live performances and a crowd fully leaning into the celebration. But the real show wasn’t onstage—it was overhead. Rogue fireworks launched from balconies, flares lit up the night sky, and at one point, I swear I heard actual gunshots. (I thought I was imagining things, but… I wasn’t.) It was loud, chaotic, kind of lawless—and completely unforgettable.
Over the years, I’ve made it a tradition to ring in the New Year in a different city. I don’t need fireworks to be timed—I just want to feel alive somewhere unfamiliar. Sicily gave me exactly that.
And maybe a little hearing loss.
Final Thoughts
This journey wasn’t just about sightseeing—it was about immersion. In Sicily, I found a place that wasn’t trying to impress me, yet somehow did. A place where things didn’t always work, but often worked out. Where I came expecting beautiful ruins and pistachio desserts, but left with something harder to pin down: a deeper appreciation for pace, for unpredictability, and for just being somewhere that made me feel present.
And let’s not forget—the ruins, the history, the sheer beauty of these crumbling, glorious buildings. You walk around Sicily and it’s like time folds in on itself: ancient columns beside chaotic markets, baroque facades glowing at golden hour, churches older than your country.
Coming from the fast-paced rhythm of Singapore, it took a while for me to slow down. At first, I was still checking my phone for updates, mentally calculating step counts, trying to optimise each day. But eventually—somewhere between a missed train and a two-hour lunch—I got the hang of it. Sicily doesn’t rush. And after a while, neither did I.
I used to think Sicily was mainly for retirees—a sun-drenched escape where seniors go to sip wine and stare at ruins in peace. But now? I get it. I really do. Sicily has a way of getting under your skin, no matter how old—or young—you think you are. It appeals to everyone. Or maybe… maybe I’m the one getting old?
Wait. Am I old?
I mean, I’m only in my mid-40s…
But I booked places for the sunset view. I avoided crowds. I came home by 8pm. I travel with compression socks now.
Oh no.
Is Sicily for seniors, or have I just… become the target audience?
Existential crisis aside, if you’re planning your own Sicilian escape—whether in winter or another season—I hope this post gives you a starting point. Or at least the gentle nudge to go.
Because sometimes, it’s not about seeing everything. It’s about showing up, letting the place surprise you, and giving yourself the freedom to wander (and get mildly lost) along the way.
Sicily surprised me. Moved me. Slowed me down. And it’s the kind of place I know I’ll return to—not just because there’s still more to see, but because it’s a place that stays with you.
So yes—I will definitely return.
Planning your own trip?
If you’ve made it this far, thank you for wandering through Sicily with me.
But if you’re now itching to get the basics quickly…
Want the Quick Version?
If you’d like a quick look at what each city has to offer—what to see, eat, explore, and how to get around—I’ve created practical guides for each one.
Check out the short-form city guides here: – Coming soon!
- Taormina
- Catania
- Ortigia
- Palermo
- Rome to Sicily by Train