| Catanzaro | Cosenza | Crotone |
| Reggio Calabria | Vibo Valentia |

Calabria was first settled by Italic Oscan-speaking tribes. Two of these tribes included the Oenotri (roughly translated into the 'vine-cultivators') and the Itali. Greek contact with the latter resulted in the entire peninsula (modern Italy) taking the name of the tribe.
Greeks settled heavily along the coast at an early date and several of their settlements, including the first Italian city called Rhegion (Reggio Calabria), and the next ones Sybaris, Kroton (Crotone), and Locri, were numbered among the leading cities of Magna Graecia during the 6th and 5th centuries BC. Conquered by the Romans in the 3rd century BC, the region never regained its former prosperity.
The Greeks were conquered by the 3rd century BC by roving Oscan tribes from the north, including a branch of the Samnites called the Lucanians and an offshoot of the Lucanians called the Bruttii. The Bruttii established the main cities of Calabria, including the modern capital, Cosenza (then called Consentia).
After the fall of the Roman Empire the inhabitants were in large part driven inland by the spread of malaria and, from the early Middle Ages until the XVII century, by pirate raids. Calabria was devastated during the Gothic War before it came under the rule of a local dux for the Byzantine Empire. In the 9th and 10th centuries, Calabria, which had been the rich breadbasket of Rome before Egypt was conquered, was the borderland between Byzantine rule and the Arab emirs in Sicily, subject to raids and skirmishes, depopulated and demoralized, with vibrant Greek monasteries providing fortresses of culture. In the 1060s, Normans under the leadership of Robert Guiscard's brother Roger established a presence in this borderland, and organized a government along Byzantine lines that was run by the local Greek magnates of Calabria. In 1098, Pope Urban II named Roger the equivalence of an apostolic legate.