The Monastery of Agios Nikolaos (St. Nicholas) Anapausas lies on a hill a short distance from the village of Kastraki, and is built on one hundred and forty-three stepped levels.

Visitors enter the monastery complex after climbing eighty-five rock-cut steps. Space limitations on the flat summit meant that the monastery had to be built upwards rather than outwards. Access to the main living area is gained via the small narthex in the catholicon ; to the right of this, after ascending successive flights of steps, visitors see the refectory, the cells and other areas before reaching the rock plateau at the top, which commands a stunning view.

Both the origin of the name, Anapausas, and the date of first habitation on the rock remain unclear. The name is at times attributed to the etymology of the word, from the verb “to rest”, and at times linked in an unsubstantiated way to the name of an original founder. The monastery is believed to have been founded in the 14th century, when the first catholicon was built. Scholars see it as contemporary with the Chapel of Agios Antonios (St. Anthony), where wall paintings dating to the same century still survive.

The catholicon as it now stands was built in the early 16th century. It is an irregularly shaped building, tailored to fit the rock plateau: a compacted cross-in square church, with a dome supported by shallow pointed vaults. On the east side of the building is an irregular Bema with a low conch , and on the west a timber-roofed lite with a small niche. According to the inscription painted on the eastern wall of the lite, above the door leading to the nave, the paintings in St. Nicholas Anapafsas were commissioned in 1527 on the initiative of a deacon named Cyprianus, and are attributed to Brother Theophanes Strelitzas Bathas, a Cretan monk. The paintings in Agios Nikolaos are his first large-scale composition, and display consummate skill in dividing up what is a lavish iconographic programme on numerous themes, with individual scenes the size of portable icons. The artist’s gifts are evident in this monument, which further exhibits influences from Palaeologan art: a firm and confident hand; harmonious, balanced scenes free of anecdotal elements; an emphasis on doctrinal content; clarity of composition; soft colors in harmonious combinations; detailed rendition of faces deep in thought, with a profound humanism. The themes are mainly drawn from the Christological cycle, although some subjects previously unknown to monumental art are shown, such as the scene of Adam naming the animals. The paintings in the small church at St. Nicholas Anapafsas not only mark the inception of Theophanes’ career as an artist in mainland Greece, but also stand as the forerunner of the Cretan School, the formal artistic expression of the Orthodox Church during the Ottoman period.