[1] After the fall of the Western Roman Empire, Taormina continued to rank as one of the more important towns of the island, following the history of Sicily in being ruled by successive foreign monarchs.
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.
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.
[6] Tyndarion was one of those who concurred in inviting Pyrrhus into Sicily (278 BC), and when that monarch landed with his army at Tauromenium, joined him with all his forces, and supported him in his march upon Syracuse.
[8] Tauromenium continued to form a part of the kingdom of Syracuse until 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.
[10] The city, however, suffered severe calamities during the Servile War in Sicily (134–132 BC), 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 Publius 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.
[11] Tauromenium again played a conspicuous part during the Sicilian wars of Sextus Pompeius, son of Pompey the Great, and, from its strength as a fortress, was one of the principal points of the position which he took up in 36 BC, for defence against Octavian (later Imperator Caesar Augustus).
[12] The victor selected Tauromenium 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.
The troops sacked the town destroying the top part of the Middle Tower that divides Taormina between the ancient Greco-Roman section and the later medieval southern zone.
Under the Bourbon dynasty of the Kingdom of Two Sicilies, which lasted until 1860, Taormina did not have a relevant role; however, it obtained an easier access when the Catrabico promontory was partially cut and a seaside road connecting it to Messina and Catania was created.
Travellers, usually well-off northern European men on a sort of Grand Tour, brought Taormina, and especially the ruins of the Ancient Greek theatre, to international attention.
Edward Chaney, an expert on the evolution of the Grand Tour and of Anglo-Italian cultural relations, described the town as attracting "male refugees from more repressive climates";[22] the Labouchere Amendment, under which Oscar Wilde had in 1895 been sentenced to two years' hard labour, made Britain particularly risky to live in.
Richard Wagner and his wife Cosima spent the 1881-1882 winter and early spring in Sicily, and on a day trip to Taormina, the composer expressed the wish that "we should have fled there in 1858 and spared ourselves many torments.
Arthur Rubinstein reported the difference in Szymanowski: "Karol had changed; I had already begun to be aware of it before the war when a wealthy friend and admirer of his invited him twice to visit Sicily.
Just after the turn of the century, Douglas Sladen published Sicily: A New Winter Resort, and by 1904 Taormina had seven hotels, whereas a generation before there had been only one, according to Bernard Berenson, an American art historian.
[22] The experienced journalist Elizabeth Bisland, who had raced around the world in competition with Nellie Bly, arrived in Taormina for a more leisurely stay in early 1908; somehow her hotel booking had gone astray, and she describes in Seekers in Sicily traipsing up and down the town, seeking a room for the night.
[46] Ethel Smyth, the English composer, travelling in 1920 with the Irish novelist Edith Somerville, found Taormina full of "colonies of Oscar Wilde-men".
Icelandic writer Halldór Laxness, who won the Nobel Prize in Literature in 1955, wrote most of his first novel, Vefarinn mikli frá Kasmír ("The Great Weaver from Kashmir"), in Taormina during the summer of 1925; he praised the town highly in his book of autobiographical essays, Skáldatími ("The Time of the Poet", 1963).
As they were holidaying on the royal yacht nearby, they sent a message to their former courtier, Alec Hood, and he welcomed them to La Falconara, where a plaque in the garden commemorates their visit.
On 9 July 1943, the feast of the patron saint Pancrazio, two separate Allied bombardments killed over 100 civilians and caused considerable destruction in parts of the southern end around Porta Catania.
After the war, Acton was visiting Taormina with Evelyn Waugh and, coming upon a board advertising "Ye Olde English Teas” he sighed and commented that the town 'was now quite as boring as Bournemouth'.
She intended to sell, but ended up staying, running the place as a pensione for half a century, with guests such as Bertrand Russell, Roald Dahl, Henry Faulkner, and Tennessee Williams.