William Shakespeare is one of the world’s best known playwrights and quite a few of his plays are somehow connected to Italy and its culture. This research paper takes a closer look at these connections between the Bard and Italy, focusing mainly on two of his plays, The Merchant of Venice and Romeo and Juliet. The analysis of the Italian novellas by authors Matteo Bandello, Masuccio Salernitano, Luigi Da Porto and Giovanni Fiorentino underlines the similarities and differences between them and the plays and provides new findings on this topic. The first part is of theoretical nature and its function is to explain the conditions in England during the Elizabethan period and compare them to the state of the Apennine peninsula during the period of the Italian city-states. The theoretical part functions as the basis for understanding political, religious and cultural aspects of the two diverse societies and additionally explains the aspect of intertextuality and the representation of cities in literature. The analytical part uses the theoretical information provided at the beginning of the paper and, by means of detailed textual analysis, connects the Italian sources to Shakespeare’s plays.