In the present study, the author presents some aspects of monastic life in Palestine in the fifth and sixth centuries as reflected in the writings of Cyril of Schitopolis. There are presented both elements related to the practical and material organization of monastic establishments and communities, especially of the Great Lavra of Saint Sabbas, as well as the spiritual path of the monk from novice to hermit. Further on, both the characteristics and rigors of a novices life in the monastery are underlined. The conditions and criteria for the authentic advancement of the monk and his ascent to a higher degree of spiritual life are synthesized on the basis of the texts. The study is completed by the exposition of Cyrils vision regarding the relations between the sacramental and spiritual hierarchy.