Experience the magic of a weekend in Sicily, complete with ancient ruins, indulging in Sicilian cuisine, and immersing yourself in the island's rich history... the largest island in the Mediterranean!
Imagine turning a corner in a quaint town to face a cobblestone alley, each stone having watched passersby for centuries. Now, imagine standing under a crescent moon, witnessing ancient ruins bathed in a warm, ethereal glow. Now, an old church clock tower that puts on a mechanical show not just with the minutes ticking by, but also with each day, month, and liturgical season. This is what you can expect from a weekend in Sicily.
Sicily, the largest island in the Mediterranean, is a treasure trove of cultural wonders and natural beauty. A part of Italy, it’s just a short ferry ride away from Calabria (not far from the beautiful town of Reggio Calabria). In just two short days of a whirlwind trip to this enchanting island, I was left wanting to come back again and again, proving why a quick jaunt to Sicily deserves a top spot on your travel bucket list.
A Weekend in Sicily: From Calabria to Cannoli
Our adventure began early Saturday morning, departing from Calabria at 6:30 AM. The journey itself was a treat, as we drove aboard a ferry crossing the Messina Strait and were able to explore during the short half-hour ride (yes, the same Messina Strait I talked about in my post about the myths of the town of Scilla, including the story of Scylla and Charybdis and the legend of the Strait). Here, I had my first taste of a true Sicilian cannoli—crispy on the outside, creamy on the inside, and just the right touch of sweetness. I think it surprised me how much I enjoyed it, with my cousin remarking that it was “just a ferry cannolo,” not a real, good pastry from a proper bakery. Nonetheless, it was an indulgent welcome to Sicilian soil and—comparing it to Canadian cannoli—it was an undeniable upgrade.
As we docked in Messina, the excitement was palpable, and I was excited to get back into the car, drive onto the island, and officially start our weekend in Sicily.
Taormina’s Historic Sites, Labyrinthine Alleys, and Culinary Delights
Our first stop was in Taormina, less than an hour’s drive from Messina. We left the car in a car park and took a free shuttle bus into town, where it left us by the main front gates. The town's allure was immediate; I was entranced by the quaint shops, friendly shopkeepers, and charm of the old streets, my eyes roving all over the place as I drank in the atmosphere.
Our first official stop was the Teatro Antico di Taormina, an ancient Greco-Roman theatre that offers not just historical significance, but also panoramic views of the azure waters surrounding it. Strolling around an ancient Greek theatre in the present day transports you to a bygone era when amphitheatres were the place to see and be seen. After all, nothing says “epic drama” quite like an active volcano looming in the distance, right?
From here, we continued to walk through the old town, enchanted by the maze of narrow alleys, each turn revealing charming boutiques and inviting cafés. Our exploration led us to Parco Florence Trevelyan, a serene garden with an abundance of beautiful blooms and trees that seemed as ancient as the theatre we had just visited. It was a verdant escape that contrasted beautifully with the bustling town streets just outside of its iron gates.
Hunger (and the need to not spend all my money in the shops) eventually guided us to Re di Bastoni Pub, where we ordered panini and cold Fantas to tide us over until our next stop on our Sicilian road trip.
Agrigento (and Ancient Ruins) Under the Stars
Our journey continued to Agrigento, though not without its hitches—delays and navigating through tight streets laden with the echo of history (and people…and cars) had other plans for us. However, the real magic still happened as night fell over the Valley of the Temples. The ruins, spectacular under the moon's spotlight and artificial lighting, transported us back thousands of years.
There’s something so magical about ancient sites like these, and I really can’t get enough of them. You could bring me to ancient site after ancient site, day after day, and I would be like a kid in a candy shop. I will never say “no” to a history field trip. For this particular UNESCO World Heritage Site, you will feel like a mortal walking among the gods—and it’s the coolest feeling ever.
After a few hours admiring the temples that span 1,300 hectares (over 3,200 acres), we were once again famished. Thus, our culinary needs eventually pulled us back to the present, leading to a late-night hunt for food. We settled on a cozy eatery serving traditional Sicilian dishes, where I revelled in a plate of pasta sprinkled with pistachios and cherry tomatoes; it was absolutely a meal worth every second of the search.
Spiritual Mornings and Historical Revelations
The following morning in Agrigento was quieter, and despite it being a Sunday morning, a visit to the Cathedral of Saint Gerland offered a peaceful moment to admire the majestic architecture and artwork inside, as it was not bustling with people attending mass.
Soon after, we were on our way back to Messina, where my cousin Vittoria shared tales of the city’s storied past, from ancient Greek settlers to the Sicilian Vespers. This was about the revolt against the French-born king Charles I of Anjou, who had controlled the Kingdom of Sicily since 1266. During Easter of 1282, the Sicilian Vespers began and, in particular, there was a surprise attack on the city on August 8th during the night. Charles's army attempted to storm the city from the hills, but on the wall, two women were keeping watch: Dina and Clarenza. They made every effort to fend off the onslaught as soon as they spotted the adversaries; Clarenza rang the bells in the Duomo's campanile (bell tower), waking the entire city, while Dina continuously tossed boulder-like rocks at the invading soldiers. Because of them, Messina was saved.
To bring this story full circle, we visited the astronomical clock in the Duomo’s bell tower at the Cathedral of Messina. A marvel of engineering and artistry that celebrates both history and myth, the bells at the top of the tower depict Dina and Clarenza, who ring them every 15 minutes, beginning a mechanical procession that begins a chain of events at every level below, each with its own mechanical carousel.
The carousel of the days of the week brings ancient deities to life, each represented by a classical figure in a chariot drawn by a distinct animal, marking the passage of time. This changes, as you can expect, once a day. Alongside, the carousel of the ages of life features statues representing the stages of human life—child, young man, warrior, and old man—each appearing in succession before the grim figure of Death, who brandishes a scythe. This moves every 15 minutes, with the next figure in the ‘life’ taking centre stage, with the child at the hour and Death at the last quarter of the hour. At midday, a spectacular scene unfolds as a dove circles and the Sanctuary of the Madonna at Montalto rises, commemorating its historical foundation.
Biblical scenes change with the liturgical season, enriching the spiritual narrative of the church it was built for. The poignant moment when an angel delivers the Madonna of the Letter to the patron saint of Messina, observed by St. Paul and ambassadors, completes this tableau, making the astronomical clock not just a keeper of time, but a storyteller of the city’s legends.
Messina: A Culinary Farewell to a Weekend in Sicily
Before we returned to the ferry docks, we indulged one last time in Sicilian cuisine at Rosticceria Fratelli Famulari, an eatery my cousin had been telling me about since she first came to visit us in Toronto in 2019. Even though we had to wait in a line that went out the door, it was so worth it, and I could not recommend this place more. The savoury pastries and arancini were a fitting end to our culinary adventure, each bite a mosaic of flavours that encapsulated the spirit of Sicily (there was even a vegan arancino, which was so delicious!).
We devoured these in a small piazza a few blocks away, sitting on a park bench under the shade of a gigantic tree as we watched the pigeons and church bells provided us with a lunchtime soundtrack.
All in All
A weekend in Sicily, with its rich history, vibrant culture, and mouthwatering cuisine, offers an escape from the everyday and into the extraordinary. Even a short trip can unfold in a tapestry of experiences, but if you can stay longer, don’t limit yourself. This island seems to be a culture all on its own, a part of Italy, but also distinctly wonderful in so many ways.
Trust me, the stories you’ll bring back will be ones you’ll talk about and share for years to come.
Exploring Sicily sounds like a dream! This guide provides a perfect mix of cultural and natural experiences, making it an ideal getaway for adventure lovers and relaxation seekers alike.
I have always heard such great things about Sicily. It sounds wonderful and I love your photos!
This post captures the essence of Sicily wonderfully. The mix of history, culture, and stunning landscapes makes it a top travel destination.
A weekend in Sicily sounds like an amazing adventure! Exploring the largest island in the Mediterranean offers a perfect blend of history, culture, and stunning landscapes. I'm part Italian and I would love to someday get to visit there.