This paper was conceived to investigate some central issues related to the upheaval of current energy scenarios in Sicily. New power connection lines that are about to be built in the Mediterranean area, planned with a view to a constantly increasing renewable generation, encourage the carrying out of analyses on how the Sicilian electric power system will be able to make itself ready to support large power injections, especially due to new renewables plants that will be established in the region soon. This study, carried out in close collaboration with the Italian TSO Terna S.p.A and the University of Palermo, defines what the impacts of new renewable power plants will be on the Sicilian power transmission grid under intact and non-intact grid conditions. This study consists of steady-state simulations carried out using WinCreso® software version 7.62.1-3 in two energy scenarios estimated for the years 2024 and 2027, based on real connection requests by producers to Terna, and allows one to go beyond the studies conducted so far on a 2030 basis through the precise identification of network nodes or lines in difficulty. Finally, as well as presenting an interesting case study due to Sicily’s strategic position in the Mediterranean Sea, this article proposes a methodological approach that can easily be adopted in other contexts and by other TSOs to analyze similar situations.