William Whitfield joined the City of Florence as 2nd Radio Officer on November 2nd, 1939, aged 17 years and 8 months. The City of Florence was involved in landing B.E.F. equipment and stores at French ports and had a part in the B.E.F. evacuation from Brest, leaving for Falmouth 36 hours before the port's capture by the Germans. His next voyage was with convoy OB216 that lost 4 ships within 2 days and another was lost later. This voyage took him to Alexandria via Durban and the Suez Canal. City of Florence was employed moving stores in the Mediteranean before sailing back through the Canal to Aden and onto Rangoon, sailing independently in the Indian Ocean. The return was back round the Cape to Freetown and a convoy (SL73) home around the north of Scotland (Oban - Methil) passing Dunnet Head on the May 25th, 1941, and with convoy FS 502 down the East coast to Southend.