Taormina's coastal location, facing Greece, between the powerful cities of Syracuse and Catana to the south, and Messana (and behind it, mainland Italy) to the north, determined much of its history. It is only about 5 km from the site of the ancient Naxos, and there is no doubt that Tauromenium did not exist as a city till after the destruction of Naxos by Dionysius I of Syracuse, 403 BCE; but the circumstances connected with its foundation are somewhat confused and uncertain.
It appears, however, from Diodorus that after the destruction of Naxos, the remaining inhabitants of that city were driven into exile, and its territory was assigned by Dionysius to the neighbouring Siculi. These, however, did not re-occupy the site of the ancient city, but established themselves on a hill to the north of it, which was called the hill of Taurus (ὁ λόφος ὁ καλούμενος Ταῦρος). Here they at first constructed only a temporary camp (in 396 BCE), but afterwards erected walls and converted it into a regular fortress or town, to which they gave the name of Tauromenium. (Diod. xiv. 58, 59.) The place was still in the hands of the Siculi in 394 BCE, and they held it against the efforts of Dionysius, who besieged the city in vain for a great part of the winter, and though he on one occasion forced his way within the walls by a nocturnal surprise, was again driven out and repulsed with heavy loss. (Id. 87, 88.) But by the peace concluded in 392 BCE, it was expressly stipulated that Tauromenium should be subject to Dionysius, who expelled the greater part of the Siculi that had settled there, and supplied their place with his own mercenaries. (Id. 96.) From this time we hear no more of Tauromenium till 358 BCE, when we are told that Andromachus, the father of the historian Timaeus, brought together all the remains of the exiled Naxians, who were still scattered about in different parts of Sicily, and established them all at Tauromenium. (Id. xvi. 7.) This is related by Diodorus as if it were a new foundation, and even as if the name had then first been applied to the city, which is in direct contradiction with his former statements. What had become of the former inhabitants we know not, but there is little doubt that the account of this resettlement of the city is substantially correct, and that Tauromenium now for the first time became a Greek city, which was considered as taking the place of Naxos, though it did not occupy the same site. (Wesseling, ad Diod. xiv. 59.) Hence Pliny's expression, that Tauromenium had formerly been called Naxos (Plin. iii. 8. s. 14) is nearly, though not strictly, correct.
The new settlement seems to have risen rapidly to prosperity, and was apparently already a considerable town at the time of the expedition of Timoleon in 345 BCE. 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. (Diod. xvi. 68; Plut. Timol. 10.) 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. (Diod. l. c.; Plut. l. c.) It is certain that Andromachus was not deprived of the chief power, when all the other tyrants were expelled by Timoleon, but was permitted to retain it undisturbed till his death. (Marcellin. Vit. Thucyd. § 27.) We hear, however, very little of Tauromenium for some time after this. It is probable that it passed under the authority of Agathocles, who drove the historian Timaeus into exile; and some time after this it was subject to a domestic despot of the name of Tyndarion, who was contemporary with Hicetas of Syracuse and Phintias of Agrigentum. (Diod. xxii. Exc. H. p. 495.) Tyndarion was one of those who concurred in inviting Pyrrhus into Sicily (278 BCE), and when that monarch landed with his army at Tauromenium, joined him with all his forces, and supported him in his march upon Syracuse. (Diod. l. c. pp. 495, 496.) A few years later we find that Tauromenium had fallen into the power of Hieron of Syracuse, and was employed by him as a stronghold in the war against the Mamertines. (Id. p. 497.) It was also one of the cities which was left under his dominion by the treaty concluded with him by the Romans in 263 BCE. (Diod. xxiii. p. 502.) This is doubtless the reason that its name is not again mentioned during the First Punic War.
Taormina as seen from the Saracen castle overlooking the town. The Greek amphitheatre is visible in the distance.
There is no doubt that Tauromenium continued to form a part of the kingdom of Syracuse till the death of Hieron, and that it only passed under the government of Rome when the whole island of Sicily was reduced to a Roman province; but we have scarcely any account of the part it took during the Second Punic War, though it would appear, from a hint in Appian (Sic. 5), that it submitted to Marcellus on favorable terms; and it is probable that it was on that occasion it obtained the peculiarly favored position it enjoyed under the Roman dominion. For we learn from Cicero that Tauromenium was one of the three cities in Sicily which enjoyed the privileges of a civitas foederata or allied city, thus retaining a nominal independence, and was not even subject, like Messana, to the obligation of furnishing ships of war when called upon. (Cic. Verr. ii. 6. 6, iii. 6, v. 19.)
But the city suffered severe calamities during the Servile War in Sicily, 134-132 BCE, having fallen into the hands of the insurgent slaves, who, on account of the great strength of its position, made it one of their chief posts, and were able for a long time to defy the arms of the consul Rupilius. They held out until they were reduced to the most fearful extremities by famine, when the citadel was at length betrayed into the hands of the consul by one of their leaders named Sarapion, and the whole of the survivors put to the sword. (Diod. xxxiv. Exc. Phot. p. 528; Oros. v. 9.) Tauromenium again bore a conspicuous part during the wars of Sextus Pompeius in Sicily, and, from its strength as a fortress, was one of the principal points of the position which he took up in 36 BCE, for defence against Octavian. It became the scene also of a sea-fight between a part of the fleet of Octavian, commanded by the triumvir in person, and that of Pompeius, which terminated in the defeat and almost total destruction of the former. (Appian, B.C. v. 103, 105, 106-11, 116; Dion Cass. xlix. 5.) In the settlement of Sicily after the defeat of Pompey, Tauromenium was one of the places selected by Augustus to receive a Roman colony, probably as a measure of precaution, on account of the strength of its situation, as we are told that he expelled the former inhabitants to make room for his new colonists. (Diod, xvi. 7.) Strabo speaks of it as one of the cities on the east coast of Sicily that was still subsisting in his time, though inferior in population both to Messana and Catana. (Strab. vi. pp. 267, 268.) Both Pliny and Ptolemy assign it the rank of a colonia (Plin. iii. 8. s. 14; Ptol. iii. 4. § 9), and it seems to have been one of the few cities of Sicily that continued under the Roman Empire to be a place of some consideration. Its territory was noted for the excellence of its wine (Plin. xiv. 6. s. 8), and produced also a kind of marble which seems to have been highly valued. (Athen. v. p. 207.) Juvenal also speaks of the sea off its rocky coast as producing the choicest mullets. (Juv. v. 93.) The Itineraries place Tauromenium 32 miles from Messana, and the same distance from Catana. (Itin. Ant. p. 90; Tab. Peut.) It continued after the fall of the Roman Empire to be one of the more considerable towns of Sicily, and from the strength of its position was one of the last places that was retained by the Greek emperors; but it was taken by the Saracens in 906 after a siege of two years, and totally destroyed.
In the late 19th century Taormina gained some prominence as the place where Wilhelm von Gloeden worked most of his life as a photographer of predominantly male nudes. Also credited for making Taormina popular was Otto Geleng, best known in his hometown of Berlin for his fine paintings, which he composed and painted in Italy but exhibited in Germany. What distinguishes Geleng, however, is his choice to depict the more southern regions where he captured the spectacular views and light of Sicily. He often painted the area's Greek colonial ruins, including Taormina.Taormina's first important tourist was Johann Wolfgang Goethe who dedicated exalting pages to the city in his book entitled "Journey to Italy," but perhaps it was Geleng’s views that made its beauty talked about throughout Europe and turned the site into a famous tourist center. The artist arrived in Sicily at the age of 20 in search of new subjects for his paintings. On his way through Taormina he was so enamoured by the landscape that he decided to stop for part of the winter. Geleng began to paint everything that Taormina offered: ruins, sea, mountains, none of which were familiar to the rest of Europe. When his paintings were later exhibited in Berlin and Paris, many critics accused Geleng of having an ‘unbridled imagination’. At that, Geleng challenged them all to go to Taormina with him, promising that he would pay everyone's expenses if he were not telling the truth.
During the early 20th century the town became a colony of expatriate artists, writers, and intellectuals. D. H. Lawrence stayed here at the Fontana Vecchia from 1920 to 1922, and wrote a number of his poems, novels, short stories, and essays, and a travel book, Sea and Sardinia. Charles Webster Leadbeater, the theosophical author, found out that Taormina had the right magnetics fields for Jiddu Krishnamurti to develop his talents, so the young Krishnamurti dwelt here from time to time. Halldór Laxness, the Icelandic author, worked here on the first modern Icelandic novel, Vefarinn mikli frá Kasmír.