This essay explores Italian mercantile perceptions of the non-western Mediterranean world during the late Middle Ages. In particular, it analyzes the corpus of merchant manuals known as "pratiche della mercatura" and argues that the intercultural and cross-confessional material included in these handbooks were vital components that helped facilitate trade across ethno-religious frontiers in the Arab-Turkic regions. This paper opens with an examination of the "traditional" manual genre, with particular emphasis on Francesco Pegolotti's "Libro di divisamenti di paesi" (c. 1310-40). Pegolotti and other "pratiche" compilers proffered practical counsel on linguistic exchange, local folklore and customs, and resourceful intermediaries (dragomans) that could accommodate cultural assimilation for the trader abroad. The remainder of the essay builds on the fruitful historiographical shifts of recent years and identifies two additional manuals: Leonardo Frescobaldi's "Viaggio in Egitto" (c. 1390) and Goro Dati's "Sfera" (c. 1435). These texts, cascaded to a wide merchant audience, include striking language on the common theological underpinnings of Islam, Judaism, and Christianity. These two authors, and specifically Dati, also highlight the complex character of the Italian merchant and reveal that economic self-interest helped construct common ground across major barriers of faith in the medieval Mediterranean.