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 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 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 BC, 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.)
After the fall of the Normans and of their heirs, the Hohenstaufen, Taormina followed the history of Sicily under the Angevines and then the Aragonese. In 1410 King Martin II of Sicily was elected here by the Sicilian Parliament. Later Taormina was under Spanish suzerainty, receiving the title of City in the 17th century.
In 1675 it was besieged by the French, who had occupied Messina. Under the Bourbons dynasty of the Kingdom of Two Sicilies, Taormina had not a relevant role; it anyway obtained an easiest access when part of the Catrabico promontory was partially cut and a seaside read connecting it to Messina and Catania was created. It received also a station on the second oldest railroad in the reign. Starting from the 19th century Taormina became a popular tourist resort in the whole Europe: people who spent vacation in Taormina include Oscar Wilde, Nicholas I of Russia, Johann Wolfgang von Goethe, Nietzsche (who here wrote his Also sprach Zarathustra), Richard Wagner and many others.
In the late 19th century Taormina gained further 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.
By this time Taormina had become "a polite synonym for Sodom" as Harold Acton described it. Later, however, after the Second World War Acton was visiting Taormina with Evelyn Waugh and, coming upon a board advertising “Ye Olde English Teas” he sighed and commented that Taormina 'was now quite as boring as Bournemouth'.
In March 2004, the wife of the Anglican Rector in Taormina - yes, there's a small flock there to be tended - related the following story: In 1943 the Allies bombed Taormina on San Pancrazio's Feast Day (July 9) during the celebratory procession. After that, the story goes, Pancrazio was completely discredited as the town's patron. The townfolk having concluded that his "Patronage" was obviosly ineffective.
Just south of Taormina is the Isola Bella, a nature reserve. Tours of the Capo Sant' Andrea grottos are also available. Taormina is built on an extremely hilly coast, and is approximately a forty-five minute drive away from Europe's largest active volcano, Mount Etna.
In 1927 the young Icelandic writer Halldór Laxness (born 1902) published his first major novel, Vefarinn mikli frá Kasmír (The Great Weaver of Kashmir), a panorama of social, literary, religious and sexual issues of his times. Laxness, who won the Nobel prize for literature in 1955, wrote most of his novel in Taormina which he then praised highly in his book of autobiographical essays, Skáldatími (The Time of the Poet) from 1963.
Between 1948 and 1999 the English writer Daphne Phelps lived in the Casa Cuseni designed and built by Robert Hawthorn Kitson in 1905, and entertained various friends including Bertrand Russell, Roald Dahl, and Tennessee Williams.
Many manifestations and events are organized during the summer in Taormina. The exceptional frame for pop and classical concerts, opera and important performances often recorded by television (for example, the ceremony of the Silver Ribbon Award, the Festivalbar, the Kore) is the Ancient Theatre. Since 1983, the most important performances, are realized by Taormina Arte, the cultural institution which organizes one of the most famous music, theatre and dance festivals. Inside the program of Taormina Arte there is the Taormina Film Fest, the well-known cinema festival, the heir of the Cinema Festival of Messina and Taormina, born in 1960, which for about twenty years has guessed the David of Donatello Awards with the participations of the most famous Italian film stars. During the Taormina Film Fest now are awarded the Silver Ribbons, prize created by the Italian Film Journalists.
Since 2005, in October, Taormina Arte has been organizing the Giuseppe Sinopoli Festival, a festival dedicates completely to the great conductor, died in 2001, for many years the artistic director of Taormina Arte.