The article focuses on how the method of participant observation can be applied in such an understudied and hard-to-access field as monastic communities. Monastic studies generate interest in academic circles but rarely become subjects of methodological reflection. The article fills the gap and analyzes the specifics of this method, its strengths and limitations as applied to monastic environment. The article discusses the ways of formulating a legend and two methods of gaining access to field: through official channels and church administration, “top-down,” and unofficial routes and gatekeepers, direct contacts, “bottom-up.” Predominantly referring to the research in Christian monasteries, the author examines four roles of a researcher depending on the degree of participation, they are: a guest, a pilgrim (or trudnik), a potential monk and a monk. Special attention is paid to professional identity conflicts that are solved with the help of “research bargains.” Such compromises as observing body discipline, mastering self-control skills, physical work and sometimes even participation in liturgical activities of a monastery are mentioned. Some aspects of reciprocal relations between a researcher and an informant and the ways to sustain them are examined. The paper covers several limitations of the method of participant observation in relation to the monastic environment, among them are: seasonality of rural monastic life, unsystematic nature of observation, researcher’s subjectivity, lack of access to certain areas of monastic life. In conclusion, the author draws attention to the selection of observation units, in particular, the difference in observation in small and large monasteries. The author gives first-person examples of empirical research in various monasteries which can be used as recommendations in conducting similar fieldwork. The article draws on the author’s fieldwork in Russian Orthodox monasteries since 2011, as well as the experience of Russian and foreign colleagues who study monastic communities.