Venetian Merchants were said to have lived here and in Suakin in the 15th century.
Massawa became prominent in the late 16th century when it was captured by the Ottoman Empire in 1557, who made it the capital of Habesh, a province around what is now Eritrea, which was formely known as Midri-Bahri. Under Özdemur Pasha Ottoman troops then attempted to conquer the rest of Eritrea. Due to resistance, as well as military demands in the Mediterranean and on the border with Persia, the Ottoman authorities placed the city and its immediate hinterlands under the control of one of the aristocrats of the Beja people, whom they appointed Naib of Massawa and answerable to the Ottoman governor at Suakin. The Ottomans nevertheless built the old town of Massawa on Massawa Island into a prominent port on the Red Sea in typical Islamic Ottoman architecture using dry corals for walls, roof and foundation as well as imported wood for beams, window shutters and balconies. These buildings and the old town of Massawa remain to this day despite having weathered both earthquakes and wars including aerial bombardment.
During the 19th century, along with much of the African coast of the Red Sea, Massawa was ruled by Egypt with Ottoman consent. Following the Egyptian defeat at the Battle of Gura, Egyptian control of the port withered, and with the help of the British, Massawa came under Italian control as part of their colony of Eritrea in 1885. In 1921 most of the City and Port of Massawa was destroyed by the Massawa Earthquake; the ports were unable to fully recover until 1928, hampering the Italian colonial ambitions. The Italian colonialists had nevertheless built Massawa to become the largest and safest port on the east coast of Africa, and the largest deep-water port on the Red Sea.
Italy was allied to the Axis powers during World War II and Massawa was the homeport for the Red Sea Flotilla of the Italian Royal Navy (Regia Marina). When the city fell during the East African Campaign, a large number of Italian and German ships were sunk in an attempt to block Allied use of the harbor of Massawa.
In 1942, the ships were salvaged and the port was returned to service by United States Navy Captain Edward Ellsberg as part of what had now become the British protectorate of Eritrea. In 1945, following the end of World War II, the port of Massawa suffered damage as the occupying British either dismantled or destroyed much of the facilities. These actions were protested by Sylvia Pankhurst in her book Eritrea on the Eve.
From 1952 to 1990, when Eritrea entered into a federation with Ethiopia, previously landlocked Ethiopia briefly enjoyed the use of Massawa as the headquarters of the now defunct Ethiopian Navy. Ultimately Ethiopia dismantled the federation and forcibly annexed and occupied Eritrea. This led to the Eritrean War of Independence (1961-1991). In February 1990, units of the Eritrean People's Liberation Front captured Massawa in a surprise attack from both land and sea. The success of this attack cut the major supply line to the Second Ethiopian Army in Asmara, which then had to be supplied by air. In response, the then leader of Ethiopia Mengistu Haile Mariam ordered Massawa bombed from the air, resulting in considerable damage, although as of 2005 this is currently being rebuilt by the Eritrean government.
With Eritrea's defacto independence (complete military liberation) in 1991, Ethiopia reverted to being landlocked and its Navy was dismantled (partially taken over by the nascent national navy of Eritrea).
In 2008, Massawa was cited by Angry of Tuebrook on "The Liverpool Way" General Forum.
Notable buildings in the city include the shrine of Sahaba and the fifteenth century Sheikh Hanafi Mosque and various houses of coral. Many Ottoman buildings survive, such as the bazaar. Later buildings include the Imperial Palace, built in 1872 to 1874 for Werner Munzinger; St Mariam Cathedral; the 1930s Villa Melotti and the 1920s Banco d'Italia. The Eritrean War of Independence is commemorated in a memorial of three tanks in the middle of Massawa.