Massawa in the context of "Dahlak Archipelago"

Italian Eritrea (Italian: Colonia Eritrea, "Colony of Eritrea") was a colony of the Kingdom of Italy in the territory of present-day Eritrea. The first Italian establishment in the area was the purchase of Assab by the Rubattino Shipping Company in 1869, which came under government control in 1882. Occupation of Massawa in 1885 and the subsequent expansion of territory would gradually engulf the region and in 1889 the Ethiopian Empire recognized the Italian possession in the Treaty of Wuchale. In 1890 the Colony of Eritrea was officially founded.

In 1936 the region was integrated into Italian East Africa as the Eritrea Governorate. This would last until Italy's loss of the region in 1941, during the East African campaign of World War II. Italian Eritrea then came under British military administration, which in 1951 fell under United Nations supervision. In September 1952 it became an autonomous part of Ethiopia, until its independence in 1991.

Asmara (/æsˈmɑːrə/ əs-MAHR-ə), or Asmera, is the capital and most populous city of Eritrea, in the country's Central Region. It sits at an elevation of 2,325 metres (7,628 ft), making it the sixth highest capital in the world by altitude and the second highest capital in Africa. The city is located at the tip of an escarpment that is both the northwestern edge of the Eritrean Highlands and the Great Rift Valley in neighbouring Ethiopia. In 2017, the city was declared as a UNESCO World Heritage Site for its well-preserved modernist architecture. According to local traditions, the city was founded after four separate villages unified to live together peacefully after long periods of conflict. Asmara existed as a major settlement for over half a millennium and enjoyed some importance as it stood on the trade route to Massawa. Asmara first rose to prominence during the 20th century, when it became capital of Italian Eritrea. Under Italian rule the city of Asmara experienced rapid urbanization and modernization, to the point that was called Piccola Roma.

The Ottoman–Ethiopian War was a period of military conflicts lasting from 1557 to 1589 between the Ottoman Empire and its allies on one side and the Ethiopian Kingdom on the other. The war was triggered with the Ottoman Empire invading territories of the Ethiopian Kingdom starting in 1557, when Özdemir Pasha took the port city of Massawa and the adjacent city of Arqiqo, followed by Debarwa, then capital of the Bahr Negus Yeshaq. The conflict continued over the next three decades and would only end in 1589. Afterwards, like Ottoman rule in North Africa, Yemen, Bahrain, and Lahsa, the Turks had no "effective, long term control" outside of the port and island where there was a direct Ottoman presence. As a result, the Ottomans were left with domain over Massawa, Arqiqo, and some of the nearby coastal environs, which were soon transferred to the control of Beja Na'ibs (deputies).

Yeshaq sought the assistance of Emperor Gelawdewos. Upon being reinforced by a large Abyssinian army, he recaptured Debarwa, taking all the gold the invaders had piled within. After growing disillusioned with the new Emperor of Ethiopia, Menas, he revolted with Ottoman support in 1560. He then pledged his allegiance again with the crowning of Emperor Sarsa Dengel. However, not long after, Yeshaq revolted once again with Ottoman support. He was defeated by the Emperor once and for all along with his Ottoman ally, the Beylerbey of Habesh, Ahmad Pasha, at the Battle of Addi Qarro where both were killed. The Ottomans abandoned their further territorial ambitions in 1589 after a series of defeats at the hands of the Ethiopian Emperor Sarsa Dengel.

Adulis (Ge'ez: ኣዱሊስ) was an ancient city along the Red Sea in the Gulf of Zula, about 40 kilometers (25 mi) south of Massawa. Its ruins lie within the modern Eritrean city of Zula. It was the emporium considered part of the D’mt and the Kingdom of Aksum. It was close to Greece and the Byzantine Empire, with its luxury goods and trade routes. Its location can be included in the area known to the ancient Egyptians as the Land of Punt, perhaps coinciding with the locality of Wddt, recorded in the geographical list of the Eighteenth Dynasty of Egypt.