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*Each of the Bombing of Livorno raids were done by up to 100 Boeing B-17 Flying Fortress bombers at the same time!

Units in the Mediterranean Theater of Operations (MTO) were the second-largest user of the Boeing B-17 Flying Fortress during World War II. There were a total of six combat groups (twenty-four squadrons) equipped with the bomber assigned to the Theater.

This original and heavily marked B-17 mission raid map was used during the famous. The Bombing of Livorno were raid mission conducted on the the Italian port city of Livorno. Livorno was repeatedly bombed by the Allied air forces, suffering about a hundred raids altogether, which resulted in it being among the most war-damaged cities in Italy.

Livorno, the main port of Tuscany, was considered by the Allies to be of strategic importance owing to its harbour facilities (the harbour of Livorno was one of the main ports of the Italian Tyrrhenian coast north of Rome), its marshalling yards, its shipyard (which built destroyers and corvettes for the Italian Navy), its oil refinery and other factories engaged in war production, such as the Motofides torpedo factory.

The first raid on Livorno by the USAAF took place on 28 May 1943, when a hundred Boeing B-17 Flying Fortress bombers of the 12th Air Force took off from bases in North Africa and attacked the harbour, the oil refinery and the marshalling yard. The objectives were hit (the maritime station was destroyed), but a large part of the bombs (roughly 180 tons) fell on the city, causing widespread damage, especially in the city centre and the Venezia Nuova district; 170 buildings were destroyed, including the cathedral, the Synagogue, the market hall and the Verdi and Rossini theatres, 300 were badly damaged and 1,300 lightly damaged, with the death of 249 civilians (other sources claim that the dead were about three hundred, with a thousand wounded). A bomb hit Villa Baciocchi, used as an orphanage for little girls, killing forty little girls and nuns; dozens of people were killed when the improvised air raid shelters created in the cellars of the Livornese Rowing Association were hit and collapsed. Several ships were sunk in the harbour, including the torpedo boats Angelo Bassini and Antares, the corvette FR 52, the steamer Tiziano and the auxiliary cruiser Caralis, which was loaded with ammunition and blew up, causing further damage to the harbour and to other ships.^[16] Some 20,000 people abandoned the city in the following days; the town of Rosignano, for instance, was swarmed with 8,000 refugees in one day, forcing local authorities to requisition the schools and every vacant building to house them.

A second, identical raid by 97 B-17 bombers of the 12th Air Force, targeting the same objectives, took place exactly a month later, and had identical results; about 250 tons of bombs were dropped, hitting both the objectives (the industrial area and the central station were badly damaged) and the city, causing widespread destruction and killing another 252 people. Eighty-six people died in an air raid shelter, hit by a bomb. The old light cruiser Bari was sunk in the harbour.

These two raids were the most devastating attacks suffered by Livorno during the entire war.