The first to arrive to the Mikra Aghia Anna were, in the 16th century, Saint Dionisius the Rhetor with his student Saint Mitrofanis, who came from the Stoudiou Monastery of Constantinople. In this monastic place, featuring the least vegetation due to the rocky soil, they found the complete silence and quietness they quested for.
They followed a living of strict ascetism in a cave, being faithful to their superior inner need for serenity and calmness. Saint Dionysius was particularly educated and insightful, and, thus, attracted a large number of persons, who he helped by supporting their deep faith. He was a distinguished writer and his books are found today in the Skete of Mikra Aghia Anna, as well as in Megisti Lavra and other monasteries. He inspired his student Saint Mitrofanis, who was initially a noticeable novice, and then, a spiritual father in the villages of Halkidiki. After they were deceased, new residents came to their place of residence, such as in Katounakia and in Karoulia. According to handwritten narratives and documents, in this area lived several other eminent personalities, who were distinguished as Spiritual Fathers, such as: Gregorios, Savvas, Cosmas, Daniel, Gabriel, Avimeleh, Joseph the Quiet, Gerasimos Mikragiannanitis and many others.
The 7 Caves in Mikra Aghia Anna, ranking from the top part of the Skete downwards, are the following:
- Dedicated to the Annunciation of Theotokos (Virgin Mary),
- Dedicated to the Resurrection of Christ and to the Blessed Fathers Onoufrios and Peter,
- Dedicated to the Beheading of Saint John the Prodromos,
- Dedicated to the Saint Archangels,
- Dedicated to the Assumption of Theotokos (Virgin Mary) and to the Blessed Fathers Dionisius the Rhetor and Mitrofanis,
- Dedicated to the Palpation of Saint Thomas, and
- Dedicated to the Birth of Saint John the Prodromos.
The activities of the Brotherhood of Mikra Aghia Anna Skete include arts, carpentry, chanting, and the production of incenses and perfumes.