Abstract: The problem of cross-cultural contacts is one of the most relevant topics in the research field of culturology. This article turns to the question of cross-cultural interaction on the example of medieval colonization of the maritime republics of the Apennine Peninsula. The object of this research is the economic and cultural processes of Italian expansion in the XIII–XV centuries. The subject is the commercial practices of the merchants, specifically from the republics Amalfi, Genoa, Venice, Pisa, and Florence. The goal of this article consists in the analysis of operations and practices introduced into the European economy from the culturological perspective. The leading methodological vector relies on the theory of cultural transfer developed by the French researcher Michel Espagne. It is established that that a range of economic and cultural phenomena is the product of cultural transfer. The application of M. Espagne’s theory of cultural transfer to the analysis of the phenomenon of Italian colonization is carried out for the first time, which defines the novelty of this work. The research results lies in the analysis of establishment of the economic and cultural phenomena, determination of cooperation of the republics of the Apennine Peninsula within the region and other European states and Arab culture, as well as the consideration of the republics of the Apennine Peninsula as trade partners, rather than competing countries alone. The provided materials can me valuable in the sphere of Mediterranean studies, for the development of cross-disciplinary scientific projects in the area of culturology and economics, as well as for profound research of Italian culture and the phenomenon of expansion of the republics of the Apennine Peninsula in the Middle Ages.