This paper presents and analyses traces of epistolary contacts between Serbian monastic milieus and various institutions, centres and subjects in the Polish-Lithuanian Commonwealth in the 16th–17th centuries. These contacts were closely connected with the cultural practice that dealt with travelling and collecting charitable donations for monasteries on Mount Athos (such as Hilandar) and territories under the auspices of the Patriarchate of Peć. The practice was perceived as a specific framework for intercultural relations, which are a subject of interest in this paper as well. This work tries to reconstruct the main characteristics and specificity of the contacts and relations. The main source material is taken from two 16th- and 17th-century letter writing manuals, supported and supplemented occasionally with other works.