Sicily was one of the top destinations for 2025, even listed abroad as a “must-see,” and it was certainly visited by many tourists in the summer. But if you want to experience the island in a more relaxed way, with fewer crowds and a less hot climate, it will be the ideal choice also for your September holidays. Think ahead, especially when booking a safe transfer with our vehicles, which will meet you at any Sicilian airport. For the itinerary we recommend, the reference airport is Catania Fontanarossa Airport (CTA)… although it is also possible to cover the same route by landing at Palermo Airport (PMO).
The Itinerary
The itinerary we suggest should be covered over several days. Not only because of the difficult roads, often old and winding, but also because each place deserves at least a one-day “stop” to truly admire it. Sicily is a whole universe; you can’t just “take a look” at it! Ready to experience September emotions by traveling from Taormina to Enna? Or vice versa, from Enna to Taormina?
Taormina in September
Taormina is the pearl of Sicilian tourism. Perhaps it’s become too overrated and crowded. In summer, parking lots are always full and there are many inconveniences… but in September, you can really feel the peace. Landing in Catania, you can reach the town via the A18 motorway heading to Messina, with a direct exit.
Taormina’s strong point is the views of the coast, especially the Bay of Naxos, but it’s also worth strolling along its medieval streets, the narrow alleys, and admiring the flower-filled balconies that suddenly appear around every corner. The Palazzo Corvaja, the Ancient Roman Theater, the Odeon, the Naumachie (Greek pools for naval battle games), and the splendid churches (the cathedral, San Giuseppe, Santa Caterina) complete its beauty. The panoramic IX April square is the beating heart of the city, as is the lush “Villa” – the public park.
A cable car service takes you down to valley, to the Mazzarò quarter, where you can admire and visit Isola Bella… a splendid verdant rocky islet connected to the shore by a gravel path. Not far from the center of Taormina, a few kilometers further upstream, you can visit the charming village of Castelmola.
The Alcantara Gorges
From Taormina, just a forty-minute drive along State Road 185 takes you to the Alcantara River Gorges, in the Motta Camastra area. Of course, a visit to the gorges will depend on the weather—which can be very rainy in September. In case of rain, hiking to the bottom of the gorges is not recommended, but you can admire the river from above, along a recently opened nature trail.
Climbing up to Mount Etna…
From the Alcantara Gorges, a journey of just over twenty minutes takes you up towards Mount Etna. The first interesting stop is undoubtedly the medieval village of Castiglione di Sicilia.
Famous for its churches, including the Byzantine temples of San Nicola and Cuba Santa Domenica, the town has for centuries gathered around the large castle, which offers spectacular views of Mount Etna on one side and the Alcantara Valley on the other. Outside the town stands U Cannizzu, with the remains of a 12th-century tower. The centrally located Church of Sant’Antonio was used by the famous Italian singer Lucio Dalla as the backdrop for his music video “Siciliano.”
Not far from Castiglione rises the town of Linguaglossa. This town also boasts many ancient churches, but has recently become an attraction for the colorful folk and agricultural-themed murals that decorate its squares. In the Linguaglossa area, there is a splendid centuries-old pine forest, where hiking trails lead to the summit of the volcano. Driving along Mareneve Road, from the center of Linguaglossa, climb up to the Brunek Refuge (1,450 meters) and further up to Piano Provenzana or the panoramic Citelli Refuge, with its marvelous views of Etna’s summit craters. Descending the volcano back down the valley, along the same Mareneve road and then the SS284, you will head west to continue the tour.
From Bronte to Troìna
In an hour’s drive, you can easily descend from Etna to Bronte. The city of high quality pistachios also boasts a beautiful historic area, definitely worth a visit: the baroque churches and squares, the monasteries, the famous Maniace Abbey—also known as Nelson’s Duchy (located outside the town), are worth a visit, as are the natural wonders the area offers: the Simeto River gorges, and the Centorbi Forest.
Another one-hour drive from Bronte will take you up to Troìna and you’re already in the district of Enna. This large medieval town is rich in religious architecture, but the Basilian Monastery of San Michele stands out above all else; it is now in ruins and surrounded by pastures, like a spectacular cathedral in the desert! The view from the panoramic terraces scattered throughout the city is unique! These views and streets became famous thanks to Robert Capa’s war photographs, taken during the Allied advance in World War 2. A museum in the city is now dedicated to the famous photographer.
And finally, Enna
Enna is divided into two areas, the upper town and the lower town. The heart of its historic beauty is undoubtedly the upper areas, clustered around the Lombardia Castle. In addition to the perfectly preserved castle, Palazzo Pollicarini, the Octagonal Tower, the Cathedral, and the Rock of Cerere are also worth visiting. In September, Enna has a wonderful weather, sunny and breezy but not hot at all. It is the highest district capital in Italy – and when the fog rolls in, making it even more romantic, you can take exceptional photos, both in the city and from the balconies overlooking the view of Mount Etna.
If you’re coming from Palermo airport, driving along the A19 motorway and exiting directly at Enna, you can follow this same itinerary… in reverse! (photo by Grazia Musumeci)
