Most settlement was on the small bays on the east side of the island which formed natural harbours. Settlement archaeological work was done quickly and thus did not find definitive evidence of grape cultivation on the island during this period. However, grape cultivation was common on neighboring islands and the nearby mainland during this time.

According to a reconstruction, based on the myth of Tenes, Walter Leaf stated that the first inhabitants of the island could be Pelasgians, who were driven out of the Anatolian mainland by the Phrygians. According to the same author, there are possible traces of Minoan and Mycenaean Greek influence in the island.

In the antiquity the island was known as Leukophrys and in Greek mythology it was Tenedos. It was mentioned in Homer’s Iliad.

In the medieval age it was a Byzantine possession. Towards the end of the medieval age it was left to Republic of Venice by the emperor John V Palaiologos as a ransom. In 1381 however, following Venetian Genoese War it was evacuated by the Venetians according to the Peace of Turin.

In 1455 it was annexed by the Ottoman Empire during the reign of Mehmet II. Although the Venetians tried to regain the island, in 1464 the Ottoman control was secured by Mahmut Pasha. As a result of the former evacuation, the island was uninhabited during the early years of Ottoman administration and the Ottoman Empire populated the present Bozcaada district by using tax exemption.

Ottoman Empire also restored the castle which was demolished during the Venetian-Genoese war.[6] Turks called the island Bozcaada meaning grayish island and the famous cartographer Piri Reis of the 16th century also used this name in his maps. In 1923 when the Turkish Republic was proclaimed, the island was declared a district and the only settlement in Bozcaada became the municipality and district center of Çanakkale Province.