Entertainment in Sicily is older than most countries' theatres. The Greeks built amphitheatres here in the fifth century BC and they are still in use. The Sicilian puppet theatre kept entire towns entertained for two centuries before screens existed. The modern island still treats a night out as something to dress for. The entertainment category in Sicily gathers opera and concerts at the Teatro Massimo in Palermo, classical performances in the Greek theatre of Taormina, puppet shows in Catania and Palermo, jazz festivals across the coast, summer feast days in every village, and rooftop bars in the old quarters. The best entertainment experiences in Sicily turn an evening into something you remember.

The tradition runs deep. The Greek theatre of Syracuse still hosts a classical drama festival every spring, performing Aeschylus and Euripides on stone seats over two thousand years old. The Teatro Massimo, opened in 1897, is the largest opera house in Italy and one of the most acoustically respected in Europe. The Opera dei Pupi, the traditional Sicilian puppet theatre, was inscribed on UNESCO's list of intangible cultural heritage in 2008. Summer feast days, from Saint Rosalia in Palermo to Saint Agatha in Catania, still bring entire cities into the streets for days at a time. Entertainment tours in Sicily draw on this inheritance.

For the visitor, entertainment in Sicily depends on the season and the city. Opera at the Teatro Massimo in winter. Greek drama at Syracuse in May. Puppet theatre in Palermo on a quiet Tuesday. A village feast day under fireworks in August. Search opera tickets in Sicily for the classics, live music in Palermo and Catania for the modern scene, or summer festivals in Sicily when the calendar opens up. Among the more memorable things to do in Sicily is to spend an evening the way the island wants you to. Dress well. Stay late. The night is the point.