Founded by Sicels in the fourth century B.C.E., Taormina was ruled by many including the Greeks, Romans, Byzantines, Arab-Normans, Swabians, Angevins, Aragoneses, Habsburgs, and Bourbons. This long series of dominations finally ended with the unification of Italy in 1860. Taormina’s tumultuous history left a legacy of fine architecture that merits attention. This tour offers an insight into Taormina’s outstanding historical, architectural, and cultural heritage, which made it a compulsory stop on the Grand Tour.

The itinerary starts at Porta Messina and ends at Porta Catania, the town’s two main gates. We begin at the Greek-Roman part of town, visit the impressive theatre, with its magnificent view of the Ionian Sea and the often snow-capped Etna in the background, the remains of the Odeon, and the so-called Naumachia. There is a beautiful park founded by an eccentric Englishwoman, Mrs. Trevelyan, nearby.

Making our way down narrow and winding alleys and staircases, we arrive at the central square Piazza IX Aprile which offers a breathtaking view of the bay of Naxos.

Walking along Corso Umberto, we stop to admire Palazzi with their original blend of Arabic, Gothic, and Spanish architectural styles. Other stops include Piazza Duomo with its emblematic fountain and its thirteenth century basilica. We finish our tour with medieval town fortifications, a Jewish ghetto, and the amazing medieval palazzo Santo-Stefano and its charming garden.

To continue your explorations of the city with Context, we recommend our Palermo Street Food Tour.

Our private tours are limited exclusively to travelers in your party. They are designed to provide a learning experience that is completely tailored to you and your traveling companions. Private tours give you some ability to tailor your itinerary (we'll work to match the itinerary to the interests and dynamics of your group), and more personalized time with your guide.

We meet at Porta Catania. Your route may differ according to your guide. Your confirmation email will have the exact meeting point details along with a map.

Tours operate rain or shine, but in the case of inclement weather, your expert will modify the tour so more time is spent indoors. It never hurts to be prepared; we encourage keeping an eye on the weather and bringing along an umbrella, sunscreen, water, or a hat as needed.

We do cover quite a bit of ground on this tour and therefore we recommend contacting us with any mobility questions; we will be happy to advise if the itinerary will be appropriate for you or propose modifications where necessary. Please feel free to contact us.