All ancient writers agree in representing Naxos as the most ancient of all the Greek colonies in Sicily; it was founded the year before Syracusae, or 735 BC, by a body of colonists from Chalcis in Euboea, with whom there was mingled, according to Ephorus, a certain number of Ionians. The same writer represented Theocles, or Thucles, the leader of the colony and founder of the city, as an Athenian by birth; but Thucydides takes no notice of this, and describes the city as a purely Chalcidic colony; and it seems certain that in later times it was generally so regarded. The memory of Naxos as the earliest of all the Greek settlements in Sicily was preserved by the dedication of an altar outside the town to Apollo Archegetes, the divine patron under whose authority the colony had sailed; and it was a custom (still retained long after the destruction of Naxos itself) that all Theori or envoys proceeding on sacred missions to Greece, or returning from thence to Sicily, should offer sacrifice on this altar. It is singular that none of the writers above cited allude to the origin of the name of Naxos; but there can be little doubt that this was derived, as stated by Hellanicus, from the presence among the original settlers of a body of colonists from the island of that name.
The new colony must have been speedily joined by fresh settlers from Greece, as within six years after its first establishment the Chalcidians at Naxos were able to send out a fresh colony, which founded the city of Leontini (modern Lentini), 730 BC; and this was speedily followed by that of Catana. Theocles himself became the Oekist, or recognised founder, of the former, and Euarchus, probably a Chalcidic citizen, of the latter. Strabo and Scymnus Chius both represent Zancle (modern Messina) also as a colony from Naxos, but no allusion to this is found in Thucydides. But, as it was certainly a Chalcidic colony, it is probable that some settlers from Naxos joined those from the parent country. Callipolis also, a city of uncertain site, and which ceased to exist at an early period, was a colony of Naxos. But notwithstanding these evidences of its early prosperity, we have very little information as to the early history of Naxos; and the first facts transmitted to us concerning it relate to disasters that it sustained. Thus Herodotus tells us that it was one of the cities which was besieged and taken by Hippocrates, despot of Gela, about 498-91 BC; and his expressions would lead us to infer that it was reduced by him under permanent subjection. It appears to have afterwards successively passed under the authority of Gelon of Syracuse, and his brother Hieron, as we find it subject to the latter in 476 BC. At that time Hieron, with a view to strengthen his own power, removed the inhabitants of Naxos at the same time with those of Catana, and settled them together at Leontini, while he repeopled the two cities with fresh colonists from other quarters. The name of Naxos is not specifically mentioned during the revolutions that ensued in Sicily after the death of Hieron; but there seems no doubt that the city was restored to the old Chalcidic citizens at the same time as these were reinstated at Catana, 461 BC; and hence we find, during the ensuing period, the three Chalcidic cities, Naxos, Leontini, and Catana, generally united by the bonds of amity, and maintaining a close alliance, as opposed to Syracuse and the other Doric cities of Sicily Thus, in 427 BC, when the Leontini were hard pressed by their neighbours of Syracuse, their Chalcidic brethren afforded them all the assistance in their power; and when the first Athenian expedition arrived in Sicily under Laches and Charoeades, the Naxians immediately joined their alliance. With them, as well as with the Rhegians on the opposite side of the straits, it is probable that enmity to their neighbours at Messana was a strong motive in inducing them to join the Athenians; and during the hostilities that ensued, the Messanians having on one occasion, in 425 BC, made a sudden attack upon Naxos both by land and sea, the Naxians vigorously repulsed them, and in their turn inflicted heavy loss on the assailants.
On occasion of the great Athenian expedition to Sicily (415 BC), the Naxians from the first espoused their alliance, even while their kindred cities of Rhegium (modern Reggio di Calabria) and Catana held aloof; and not only furnished them with supplies, but received them freely into their city. Hence it was at Naxos that the Athenian fleet first touched after crossing the straits; and at a later period the Naxians and Catanaeans are enumerated by Thucydides as the only Greek cities in Sicily which sided with the Athenians. After the failure of this expedition the Chalcidic cities were naturally involved for a time in hostilities with Syracuse; but these were suspended in 409 BC, by the danger which seemed to threaten all the Greek cities alike from the Carthaginians. Their position on this occasion preserved the Naxians from the fate which befell Agrigentum (modern Agrigento), Gela, and Camarina; but they did not long enjoy this immunity. In 403 BC, Dionysius of Syracuse, deeming himself secure from the power of Carthage as well as from domestic sedition, determined to turn his arms against the Chalcidic cities of Sicily; and having made himself master of Naxos by the treachery of their general Procles, he sold all the inhabitants as slaves and destroyed both the walls and buildings of the city, while he bestowed its territory upon the neighbouring Siculi.
It is certain that Naxos never recovered this blow, nor rose again to be a place of any consideration: but it is not easy to trace precisely the events which followed. It appears, however, that the Siculi, to whom the Naxian territory was assigned, soon after formed a new settlement on the hill called Mount Taurus, which rises immediately above the site of Naxos, and that this gradually grew up into a considerable town, which assumed the name of Tauromenium. This took place about 396 BC; and we find the Siculi still in possession of this stronghold some years later. Meanwhile, the exiled and fugitive inhabitants of Naxos and Catana formed, as usual in such cases, a considerable body, who as far as possible kept together. An attempt was made in 394 BC by the Rhegians to settle them again in a body at Mylae (modern Milazzo), but without success; for they were speedily expelled by the Messanians, and from this time appear to have been dispersed in various parts of Sicily. At length, in 358 BC, Andromachus, the father of the historian Timaeus, is said to have collected together again the Naxian exiles from all parts of the island, and established them on the hill of Tauromenium, which thus rose to be a Greek city, and became the successor of the ancient Naxos. Hence Pliny the Elder speaks of Tauromenium as having been formerly called Naxos, an expression which is not strictly correct. The fortunes of the new city quickly rose to be a place of importance. The site of Naxos itself seems to have been never again inhabited in antiquity; but the altar and shrine of Apollo Archegetes continued to mark the spot where it had stood, and are mentioned in the war between Octavian and Sextus Pompey in Sicily, 36 BC.
The site of the city falls into the territory of the comune of Giardini Naxos. There are no remains of the ancient city now extant, but the site is clearly marked. It occupied a low but rocky headland, now called Cape Schisò, formed by an ancient stream of lava, immediately to the north of the Alcantara, one of the most considerable streams in this part of Sicily. A small bay to the north affords good anchorage, and separates it from the foot of the bold and lofty hill, still occupied by the town of Taormina; but the situation was not one which enjoyed any peculiar natural advantages.
The coins of Naxos, which are of fine workmanship, may almost all be referred to the period from 460 BC to 403 BC, which was probably the most flourishing in the history of the city.