ONE: TAORMINA & CASTELMOLA
Taormina is iconic for good reason and is one of those places worth braving the crowds. Down in Taormina Mare, the coastline puts Isola Bella on display as if an artist had envisioned the perfect ornament for the coast. Then ride the funicular or drive up the hill and the town itself unfolds: alleys that feel like discoveries, terraces that surprise at every turn, a piazza that is essentially a sublime balcony over the Ionian, and above all, the Greek Theatre. One of the most fabulous concert halls in the world, with its stage opening onto Etna’s smoking peak and the endless coastline, it is the perfect place to be for an opera.
Above Taormina, Castelmola crowns the hill like our big little secret. The village is tiny, its alleys winding between stone houses and sudden openings onto endless views. From here, Etna and the Ionian are both in sight, vast and close at once. Sit in the main square with a glass of almond wine and you will understand why I made you climb up here: Castelmola is our pause after Taormina’s spectacle, a smaller stage with no less drama.
TWO: SYRACUSE
Syracuse is a city of two islands, where dramatic geology meets millennia of human story. Start at the Neapolis Archaeological Park: see the Greek Theatre, still hosting open-air concerts, the Roman Amphitheatre, and the Ear of Dionysius, the famous limestone cave that carries sound like a natural amplifier. Whisper, sing, or speak – your echo returns like an eerie boomerang. The playground continues at the nearby Latomie: massive stone quarries carved in ancient times, once used as prisons, now raw, cathedral-like spaces for us to dance in.
Cross the bridge to Ortigia, the island cradle of Syracuse and its oldest settlement. You can walk it through and around in two hours, and those may very well be the most beautiful two hours in Sicily. Piazza Duomo is the beating heart, dominated by the extraordinary Cathedral, actually built within a Greek temple – you can see the Doric columns – a fabulous marriage of classical and Baroque.
Wander serene streets, breathe at Fonte Aretusa, and stroll along Lungomare Alfeo, where balconies, cafés, and the Ionian breeze create cinematic moments at every turn. Ortigia in the late afternoon is simply perfection, with golden light and the contrast of the bluest sea turning everything into a living stage set.
THREE: THE BAROQUE TOWNS – Noto, Modica, Ragusa Ibla, Scicli
Sicily’s Baroque towns are true open-air museums. Rebuilt after the devastating 1693 earthquake under the patronage of wealthy aristocrats inspired by the height of the Baroque age, they radiate a dazzling, almost unreal beauty, where light seems to be directed by genius cinematography. Buildings twist and curve, façades erupt with cherubs and masks, and balconies are intricate works of decoration.
Noto is the essential Baroque city. The main street, Corso Vittorio Emanuele, is lined with golden palaces, churches, and ornate doorways. Side streets hide carved balconies, quiet squares, and tiny cafés. Sunset is the perfect time—the honey-colored stone takes on a glow no AI filter can add.
Modica goes for the chocolate. The town is famous for its grainy, aromatic chocolate, made with centuries-old methods brought by the Spanish from the Americas. Wonder at the twin grand churches, wander narrow alleys, and discover hidden cafés and peaceful piazzas.
Ragusa Ibla – what.a.find. It is a labyrinth of elegant buildings, stairways, and small gardens, with intimate squares creating unexpected views, all inviting slow exploration and slower aperitivo breaks.
Scicli is the smallest of the group, with compact streets and subtle flourishes. Perfect for a relaxed afternoon stroll or finding a local trattoria off the main drag.
FOUR: THE GULF OF CALSTELLAMMARE
Half an hour west of hectic Palermo and you are in for a treat: the immense, tame, brilliant Gulf of Castellammare offers wide beaches, shallow waters, quaint villages, and wild nature.
In Castellammare del Golfo the harbor is quiet, streets are cobbled, and trattorias are authentic. There is even a castle, and the beach is one of the best in Sicily. Deeper into the secretive coastline, Scopello hides its magical Tonnara, set beneath the towering Faraglioni.
On the westernmost side of the bay, San Vito lo Capo is a paradise for surfers and kite enthusiasts, like me: soft sand, turquoise waters, an ever-present breeze, and a lively summer scene. Trails from town lead into the Zingaro Nature Reserve, where cliffs, hidden coves, and panoramic viewpoints reward even a lazy hike.
Riserva dello Zingaro is the place to run away from the madding crowd: rugged cliffs, fragrant wild herbs, and secluded beaches make it sooo easy to lose track of time.
FIVE: ETNA
Etna, Europe’s highest active volcano, is the god of Sicily, the maker and breaker of landscape and life. Sicily owes everything to Etna: the black lava fields that nourish green vineyards and orchards, the black basalt that built Catania’s palaces, the dangerous allure of frequent eruptions, the fame, the fragility, the suspense.
As you drive up the slopes, you’ll be in for dramatic views: crater rims, rugged volcanic terrain, and on a clear day, the Ionian coastline stretching to the horizon. The drive stops at Rifugio Sapienza, but you can go further up by funicular and 4×4 buses to almost 3000m. If you time it right, a walk to the craters at sunset will reveal glowing lava fields and long shadows – the mountain is always alive. Over the past years, statistics show that we can expect an eruption every three months.
Etna’s generosity is unique. In Zafferana Etnea and Castiglione di Sicilia, vineyards produce Nerello Mascalese and Carricante, wines that owe their sumptuousness to the volcanic soil. You’d better try a tasting of two at a family-run winery.
SIX: AGRIGENTO & SCALA DEI TURCHI
Agrigento is worth the drive. Nowhere on Earth will you find a whole boulevard of Greek temples to walk in. Here, in the Valley of the Temples, Doric columns have stood in this sacred area for 2,500 years, and there are no less than seven temples and hundreds of old olive trees to create awe.
When in the area, you must head to Realmonte to see the Scala dei Turchi, the brilliant white cliffs that drop into turquoise waters. This is that perfect spot for the happy few: singular, fantasist, awe-inspiring. Here, unlike other white shores you’ve seen, the rocks are terraced, forming stairs or armchairs for you to linger like on a gigantic meditative lounge over the sea. Maybe follow it with a seaside lunch in Realmonte, where fresh pasta or seafood comes with a direct view of the cliffs meeting the sea.
SEVEN: AEOLIAN ISLANDS
The Aeolian Islands are alter-egos of Sicily : volcanic, wild, and quietly elegant. The archipelago is a UNESCO site. Ferries connect the islands multiple times a day from Milazzo or Messina, so hopping between them is easy, but a private boat tour is best.
Stromboli is famous for frequent eruptions. You can hike partway up with a guide or watch from the sea on a regular ferry – seeing the fiery bursts, especially against the night sky is unforgettable.
Panarea is tiny, exclusive, car-free and hell expensive. Early mornings are best for wandering its alleys before the day-trippers arrive. Black sandy beaches and peaceful harbor views make the island charming and quiet, but in fact it’s just sleeping. At night, the yachts arrive and Panarea becomes Rihanna’s dance floor.
Lipari and Vulcano – Lipari is a mix of colorful harbor life, volcanic rock formations, and quiet streets perfect for wandering. Don’t miss the chance to climb to the old castle for panoramic views of the island and the neighboring volcanic craters. Vulcano is famous for its sulfuric mud baths and fumaroles, but the real joy is sailing or taking a boat trip around the island, discovering hidden coves, black sand beaches, and quiet anchorages that are otherwise unreachable.
