Before I go further, I must confess a bias: My mother was born in Sicily in 1933, in Messina, just across from Reggio Calabria and the mainland.

Her father ran the local Kia Ora factory, and the family were well off for the time. They even had their own car! His death when she was 7 years old, and the war, changed all that…

And so it was that my sisters and I, whilst in our early teens, were fortunate enough to spend many summers with my great aunt in her villa, at the top of the hill in Sperone, overlooking the town, the port, and the straits of Messina.

Evenings were often spent on the patio, eating focaccia (the Messinese version doesn’t have mozzarella, just endive, anchovies, olives and a tomato base), while my parents and aunt drank iced red wine (which was delivered by tanker!) and talked.

I remember my mother often reverting to the local dialect, a language we would hear regularly on the streets whenever we ventured into the centre. After the evening meal, my sisters and I would play with the local children.

The memory of those warm, balmy evenings remains with me to this day: The lights of Reggio Calabria, twinkling across the sea; the fishing boats, with a light at the back to attract the fish, making their way out of the port – hoping to catch some Pesce Spada (swordfish), which would be sold on the dockside in the morning. And the sweet smell of jasmine wafts in on any slight breeze.

A Journey Through Time: Sicily’s Rich History

Sicily has been at the crossroads of human history in the Mediterranean for millennia. The island has welcomed Greeks, Romans, Byzantines, Arabs, Normans, and Spanish, and even the British, each leaving a lasting legacy.

Despite this, or perhaps because of it, Sicilians have always been fiercely independent. Rome is just 263 miles from Palermo by air - but in many ways, it might as well be on the other side of the planet. The flag of Sicily features a diagonal split of red and yellow, representing the cities of Palermo and Corleone, with a central triskelion (three legs) and the winged head of Medusa. Officially adopted in 2000, it symbolises the island's three capes, history of resistance, and fertility.

However, Sicilians will tell you the message of the three legs is that wherever a Sicilian lands, they'll always land on their feet.

Taormina, a cliffside jewel

What do Goethe, D.H. Lawrence, Richard Wagner, Oscar Wilde, Truman Capote, John Steinbeck, Ingmar Bergman, Francis Ford Coppola, Cary Grant, Gregory Peck, Elisabeth Taylor and Woody Allen have in common? They all took time to stay in Taormina

Perched high above the Ionian Sea, Taormina is Sicily’s postcard-perfect town, renowned for its breathtaking views and elegant charm. Its crown jewel is the Greek Roman Theatre (Teatro Antico), a 3rd-century BC marvel still hosting concerts and operas, with Mount Etna as a dramatic backdrop.

Stroll the pedestrian-friendly Corso Umberto, a lively street lined with boutique shops, gelaterias, and baroque churches - like the 17th-century Santa Caterina. Taormina’s medieval core, with narrow alleys and flower-draped balconies, exudes romance.

The town’s upscale vibe, vibrant nightlife, and proximity to Etna make it ideal for luxury travellers and culture seekers.

The summer brings crowds, so visit in spring or autumn for quieter charm.

Mount Etna: Sicily’s Majestic Volcano

Mount Etna is one of the most active volcanoes in the world. It towers over eastern Sicily, at 3,357 meters (11,014 feet), offering an unforgettable adventure for nature lovers, hikers, and thrill-seekers.

Located near Catania and easily accessible from Taormina or Syracuse, Etna combines raw natural beauty, geological wonders, and cultural significance.

Etna is not just a volcano; it’s a living, breathing force that shapes Sicily’s landscape and identity.

Its fertile slopes produce world-class wines, citrus groves, and olive orchards, while its eruptions—frequent yet rarely catastrophic—add an element of awe.

Designated a UNESCO World Heritage Site in 2013, Etna offers diverse experiences: hiking rugged trails, skiing in winter, exploring lava caves, or savouring local cuisine with views of smoking craters. Its proximity to Sicily’s cultural hubs makes it an ideal day trip or multi-day adventure.

Ortigia, Syracusa's enchanting island.

Ortigia, the historic heart of Syracuse, is a small island connected to the mainland by bridges, steeped in myth and beauty.

This baroque labyrinth captivates with its honey-coloured stone buildings and seafront promenades. The Duomo di Siracusa, a 7th-century cathedral built over a Greek temple, showcases Doric columns alongside baroque splendour.

Wander to the Fonte Aretusa, a freshwater spring tied to Greek mythology, where papyrus plants thrive. Or visit Ortigia’s market, with vendors selling spices, seafood, and almonds.

You can dine at waterfront trattorias serving pasta alle sarde (sardine pasta) or sip aperitifs in Piazza Duomo, a stunning square glowing at dusk.

Ortigia’s intimate size, historic depth, and romantic ambience make it perfect for leisurely exploration, especially at sunset.

Agrigento: Gateway to Ancient Wonders

On Sicily’s southern coast, Agrigento is synonymous with the Valley of the Temples, a UNESCO World Heritage Site and one of the world’s best-preserved Greek archaeological complexes.

This sprawling site features seven Doric temples from the 5th century BC, including the near-intact Temple of Concordia, later converted into a Christian Basilica. The Temple of Hera and Temple of Hercules offer glimpses into ancient religious life, set against almond groves and olive trees.

Various companies offer a guided tour of the park, and it's well worth taking one. The tours usually finish by early evening, and in the summer, it's worth staying on, since, as dusk turns to night, the various temples are lit, offering a mesmerising sight.

Agrigento’s modern town, perched on a hill, has a charming medieval core with winding streets and the Cathedral of San Gerlando. The streets are for pedestrians and local traffic only, and it's a steep climb to the top. But definitely worth the view!

Scala dei Turchi, Turkish Stair

On Sicily’s southern coast near Realmonte and Agrigento, is one of those places that feels almost unreal when you first see it. The name means “Stair of the Turks” and refers to the natural, staircase‑like terraces carved into brilliant white marl rock. Over centuries, wind and sea have sculpted the cliff into soft, flowing curves that tumble gently down into turquoise water. From above, the contrast between the blinding white stone and the deep blues of the Mediterranean is striking, especially in the late afternoon when the sun softens, and the colours become even more intense.

This is not just a photo stop but an experience to slow down and savour. You can walk along the shoreline, climb carefully onto the smooth steps, sit and watch the light change, or swim in the calm, clear bay below. It works beautifully combined with a visit to the Valley of the Temples in Agrigento, giving a “culture plus coast” day. 

Erice: Splendour and charm, traditions and stories of the past

Erice is one of Sicily’s most atmospheric hill towns, perched high above the western coastline and often wrapped in an ethereal mist that only adds to its charm. Reached by a winding mountain road or a scenic cable car from Trapani, it feels like stepping back in time the moment you enter through its stone gates. Narrow cobbled streets twist between ancient stone houses, little piazzas open unexpectedly, and at almost every turn there is a glimpse of the sea or the patchwork of fields and salt pans far below. With its elevated position and fortified walls, Erice has long guarded this corner of Sicily, and you can still feel that sense of watchful calm as you wander.

At the heart of Erice stands the imposing Castello di Venere, built on the site of an ancient temple dedicated to the goddess Venus. From the castle ramparts, clients are rewarded with some of the most spectacular views in Sicily: on a clear day you can see the Egadi Islands offshore, the glistening salt flats near Trapani and the curving coastline stretching away in both directions. Around it, a lacework of medieval churches and monasteries underlines Erice’s spiritual past, each with its own quiet charm. The town’s cool, often breezy climate offers a refreshing contrast to the heat on the coast below, making it a lovely daytime escape in the summer months.

Erice Locally renowned pastry shops serve traditional Sicilian sweets such as almond biscuits and genovesi, best enjoyed with an espresso or a glass of Malvasia while you pause between strolls. Artisan boutiques sell ceramics, woven textiles and local delicacies, ideal for thoughtful souvenirs. It pairs beautifully with a stay in nearby Trapani or Marsala: a day or half‑day visit to Erice gives you that romantic, storybook hill‑town experience, complete with sweeping views, evocative history and a slower, gentler pace that many remember as a highlight of their Sicilian journey.

Palermo, Sicily's Capital, is raw, hectic, but with a fascinating history.

Palermo is a city where Sicily’s many layers of history collide most vividly. Founded by the Phoenicians, shaped by the Greeks and Romans, transformed by Arab emirs and Norman kings, and later ruled by the Spanish Bourbons, it has long been a prized crossroads of the Mediterranean. You see that heritage in its architecture: Arab‑Norman churches with golden mosaics sitting beside baroque palaces, crumbling convents and elegant theatres from the 19th century. Landmarks such as the Cattedrale di Palermo, the Palazzo dei Normanni with its extraordinary Cappella Palatina, and the grand Teatro Massimo tell the story of a city that has constantly reinvented itself while keeping its soul very much intact.

What makes Palermo especially compelling for clients is that this history is not tucked away in museums; it is woven into everyday life. Narrow alleys open suddenly into sunlit piazzas; laundry flutters above faded palazzi, and religious processions might appear unexpectedly around a corner.

The old markets of Ballarò, Capo and Vucciria are like open‑air theatres: stallholders call out their wares with operatic enthusiasm, and the colours and sounds feel almost overwhelming at first. This is the Palermo that lingers in the memory: a little chaotic, unapologetically authentic and endlessly photogenic, with layers of story in every street.

Palermo is also one of Italy’s great food cities, and a must for those who love to eat their way through a destination. Its cuisine is a reflection of all those historical influences: Arab spices, Mediterranean seafood, Norman and Spanish touches, combined with the island’s own rich produce. Street food is the star here: think crisp arancini, panelle (chickpea fritters), sfincione (Palermitan pizza), crocchè (potato fritters) and, for the adventurous, pani ca meusa, a traditional spleen sandwich. In between market stalls and tiny friggitorie, you will find trattorie serving pasta con le sarde, fresh grilled fish and seasonal vegetable dishes that showcase the best of Sicilian ingredients. For clients, a guided street‑food walk or a relaxed evening tasting

Ultimately, a bucket list trip should deliver more than pretty photos. Sicily offers layered stories, generous hospitality, and the sort of sensory memories that last: the sound of church bells in Ortigia, the taste of granita on a hot morning, the glow of evening light on Noto’s facades, the crunch of ancient stone underfoot in Agrigento.

With thoughtful planning, the island lends itself beautifully to a multi‑centre journey that links Taormina, Mount Etna, Ortigia, Noto, Agrigento, Erice, Trapani, Marsala, Palermo and Cefalù into one coherent story rather than a rushed checklist.

If you would like help shaping that story, give me a call or drop me an email:

Tel: 01234 581066

Email: marco.williams@myTC.com