The area around Taormina was inhabited by the Siculi even before the Greeks arrived on the Sicilian coast in 734 BC to found a town called Naxos. The theory that Tauromenion was founded by colonists from Naxos is confirmed by Strabo and other ancient writers.
The new settlement seems to have risen rapidly to prosperity, and was apparently already a considerable town at the time of Timoleon's expedition in 345 BC. It was the first place in Sicily where that leader landed, having eluded the vigilance of the Carthaginians, who were guarding the Straits of Messina, and crossed direct from Rhegium (modern Reggio di Calabria) to Tauromenium. The city was at that time still under the government of Andromachus, whose mild and equitable administration is said to have presented a strong contrast with that of the despots and tyrants of the other Sicilian cities. He welcomed Timoleon with open arms, and afforded him a secure resting place until he was enabled to carry out his plans in other parts of Sicily. Andromachus was not deprived of his position of power when all the other tyrants were expelled by Timoleon, but was permitted to retain it undisturbed till his death.