The Mediterranean is a “hot spot” for the genesis of different types of severe weather events, including potentially damaging wind phenomena like downbursts, whose occurrence and evolution in this geographical region have not been documented in the literature. This paper is part of an interdisciplinary collaboration between atmospheric scientists and wind engineers with the objective of conducting a comprehensive analysis of the field measurements and weather scenarios related to nonsynoptic wind systems in this area. The downburst that struck the Livorno coast of Italy at about 1310 local time 1 October 2012 is investigated as a relevant test case for such severe wind events. The wind velocity records detected by ultrasonic anemometers, part of a monitoring network created for the European “Wind and Ports” and “Wind, Ports and Sea” projects, are analyzed and decomposed in order to inspect the main statistical features of this transient event. The analysis of the meteorological precursors to this event is carried out making use of model analyses, standard in situ measurements, remote sensing techniques, proxy data, and direct observations. The results obtained bring new insights into a downburst’s onset and detection in the Mediterranean, its evolution at the local scale, and possible connections to specific synoptic-scale weather conditions like secondary cyclogenesis in the lee of the Alps.