In Byzantine times, there were at least three monasteries on Heybeliada, then known as Halki. The most renowned of these was Hagia Triada, the Holy Trinity, whose site on Ümit Tepesi is occupied by the Greek Orthodox theological school of the same name, a direct descendant of the original Byzantine monastery. The present monastery is the most prominent monument on Heybeliada, dominating the view from an approaching ferry and from within the village itself.

The earliest reference to a monastery on Halki is in the writings of St. Theodore of Studius early in the ninth century. Theodore, abbot of Constantinople’s famous monastery of St. John of Studius, was exiled to a monastery on Halki by Leo V (r. 813-20) because of his criticism of the emperor’s iconoclastic policy. While on Halki, Theodore wrote a number of letters, theological treatises, and poems, one of which was addressed fondly to the monastic cell in which he was confined.

The monastery of the Holy Trinity was restored by the patriarch Photius I (r. 858-67, 877-86), who was twice exiled there, first between his two terms as patriarch and then in the years 887-90. Photius died in the monastery in 890 and was buried there; he was subsequently canonized and is today revered as the patron saint of the Theological School of the Holy Trinity.

The monastery was apparently destroyed at the time of the Turkish Conquest in 1453, moving one anonymous chronicler to lament the loss of what "had earlier been a place where wisdom and knowledge were studied, not only by monks but also by kings and noblemen." In 1550 the monastery was rebuilt or at least partially restored by the future patriarch Metrophanes III (r. 1565-72, 1579-80). Metrophanes also gave to the monastery some three hundred manuscripts, a priceless gift that formed the nucleus of what was to become one of the most renowned libraries in the Orthodox world after that of the Patriarchate in Istanbul.

Hagia Triada went through difficult times in the seventeenth and eighteenth centuries, but its finances, at least, improved after Peter the Great, Tsar of Russia (r. 1682-1725), issued a chrysobull giving the monastery a long-term endowment. The monastery was rebuilt and refurbished in 1773 through the efforts of its energetic abbot, Samuel the Deaf. The monastery was badly damaged in 1821, at the beginning of the Greek War of Independence, when it was attacked by a mob and set on fire. The monastery was rebuilt in 1844 by Patriarch Germanos IV, who decreed in a synod that "a theological school should be built for a purpose pleasing to God and dwelt in by theology teachers, priests who wish to learn, and future priests." Wooden buildings were erected to house the classrooms, study hall, teachers’ quarters, student dormitories, refectory, infirmary, and patriarchal apartments, while a two-storey stone structure was built for the library. Then in 1891 a three-storey wing was added to house the administrative offices and new dormitories. All of these structures were seriously damaged in the great earthquake of 1894. Thus a completely new building had to be erected for the monastery, all of the funds for which were provided by the philanthropist Pavlos Skylitsis Stephanovik. The new monastery was designed by the architect Pericles Photiades, and the building was officially dedicated on 6 October 1896, the archimandrite Germanos Gregoras presiding as Rector of the Theological School.

Theological School

The main entrance to the theological school is a combination of neo-classical and neo-Byzantine styles. Two monoliths of Proconnesian marble crowned with intricately carved Corinthian-type capitals divide the front of the porch, with smaller columns of the same type supporting the stilted arches of the tripartite window above. Four columns identical to those in the porch support the ornately painted ceiling of the entrance hall, from which a pair of marble stairways lead to the great reception hall on the main floor above. The walls of the reception hall are hung with portraits of patriarchs, rectors of the theological school, and others associated with the history of the monastery. At one end of the hall a niche contains the carved wooden iconostasis and its icons from the Byzantine church of the Virgin Kamariotissa on Heybeliada, which was taken over by the Turkish Navy in 1942. The patriarchal apartments, the administrative offices, and the rooms of the faculty are also on the main floor.

The classrooms of the school are situated on either side of the transverse corridor on the first floor, and the dormitories of the seminarians are in the north and south wings. The renowned library is also on the first floor as are the refectory, the infirmary, and service facilities such as the barber shop and tailor, while the gymnasium is to the south of the complex. The theological school was closed by the Turkish government in 1971, but political discussions are now under way which, hopefully, will lead to its reopening.

The monastery of St. Nicholas (Hagios Nikolaos) is on the eastern shore of the island, accessible by both the shore road and another road leading from the meydan below the summit of Yüce Tepe. The monastery is on or near the site of the Byzantine settlement of Karyes, which was abandoned in the seventeenth century after being devastated in a fire. The earliest mention of the monastery is by the English traveller Thomas Smith in 1680. The original katholikon of the monastery may have been built on and from the ruins of the parish church of Karyes. In 1783 the monastery temporarily housed a "School for Greek Classes," which subsequently was relocated near the Patriarchate in Istanbul as the Megale Scole, or Great School, which is still in existence.

When the Greek War of Independence began in 1821 the monastery was taken over by the Turkish Army. Later it was restored and served to accommodate Greek families from Istanbul on visits to Prinkipo. A fire in 1852 destroyed the interior of the katholikon, including the iconostasis and most of the icons. The church was rebuilt in 1860 according to the original design, a domed four-columned cross-in-square, the plan of virtually all Constantinople churches of the medieval Byzantine era. The supposition is that the original katholikon preserved the plan of the parish church of Karyes, which is believed to have dated from the Byzantine period. The attractive narthex, covered with a tiled roof, dates to 1873. Over the entrance there is a marble relief of a double-headed eagle, emblem of the Palaeologus dynasty, who ruled Byzantium during its last two centuries. On the exterior at the northwest corner there is an ancient Greek relief representing a chariot race.

The monastery of St. George Koudonas crowns Yüce Tepe, the southernmost of the island’s two hills. A path leads up to the monastery from the meydan at the waist of the island.

According to tradition, the monastery was founded in 963, during the reign of Nicephorus II Phocas (r. 963-9). The earliest reference to it is in the chrysobull of 1158 by Manuel I Comnenus mentioned earlier. The name Koudonas, which in Greek means "of the bells," comes from the story that a shepherd was grazing his flock on this hill when he heard the sound of bells coming from beneath the ground; when he dug down he found an icon of St. George, which he and other locals enshrined on the spot. This story is traditionally dated to the year 1625, and it probably represents the refounding of the monastery rather than a new foundation. Legend aside, the first abbot of record, Isaias, started building the present katholikon in 1752 and completed the main church of the Blachernitissa seven years later, also adding a number of monastic cells. Several additions were made in the following half century by the abbots Anthemios and Arsenios. Meanwhile a number of miracles were attributed to the icon of St. George, which was especially effective in curing mental ailments and in exorcizing those "driven by unclean spirits."

The present complex consists of six separate churches and chapels on three different levels, the older sanctuaries being on the lower levels. On the ground floor are the abbot’s house and the main church of St. George, both built early in the twentieth century. On the southern interior wall of the church is the original icon of Hagios Georgios Koudonas, now clad in silver. On a corner of the icon is a much later inscription, a moving appeal by a young Greek woman, who writes, "Dear St. George, help me go to Athens and study pharmacology."

A flight of steps leads to the first level below. Just beside the steps is a chapel of the Virgin Blachernitissa. Beyond that is another chapel of St. George, where iron rings set into the wall indicate that this was the place where mental patients were confined in the hope that they would be cured by the wonder-working icon of Hagios Georgios Koudonas. The room at the bottom of the stairs is a tiny shrine with an hagiasma, supposedly the place where the sacred icon of St. George was excavated. Beyond that is another chapel, dedicated to the Holy Apostles.

The feast day of St. George is celebrated on 23 April when thousands of pilgrims from around the world—including Muslim Turks and other non-Christians—make their way to the monastery, many of them walking barefoot up the hill to attend the dawn service. After the service many of the pilgrims have lunch at the little outdoor restaurant on the hilltop, celebrating the day that traditionally marks the beginning of spring according to the old calendar. The restaurant serves simple meals and snacks, as well as its own unlabled red wine. The hilltop is embowered in pines, cypresses, and other trees in a setting reminiscent of the Greek isles, particularly when the bells of the monastery are ringing in this ancient shrine.The feast day of St. George is celebrated on 23 April when thousands of pilgrims from around the world—including Muslim Turks and other non-Christians—make their way to the monastery, many of them walking barefoot up the hill to attend the dawn service. After the service many of the pilgrims have lunch at the little outdoor restaurant on the hilltop, celebrating the day that traditionally marks the beginning of spring according to the old calendar. The restaurant serves simple meals and snacks, as well as its own unlabled red wine. The hilltop is embowered in pines, cypresses, and other trees in a setting reminiscent of the Greek isles, particularly when the bells of the monastery are ringing in this ancient shrine.

The view from the summit of Yüce Tepe is superb, encompassing all of the Princes’ Isles and the Asian shore of the Sea of Marmara, a prospect duly praised by Grosvenor, although the villages that he mentions have now all been amalgamated into the urban sprawl of Istanbul:

The view from this peak is the most extensive which Constantinople affords. From the height of six hundred and seventy feet the eye sweeps over the sea and comprehends the eastern shores of the Marmora. Northwest, beyond the island group, the fairy outline of Stamboul and Kadikeui fringes the sky, while the sombre point of Phanaraki advances in the foreground. North and east along the sinuous Asian coast, village presses upon village, each enriching the landscape with the tints of natural beauty or association.

According to tradition, the monastery was founded in the Byzantine era, and implicit reference to it seems to have been made in a chrysobull issued in 1158 by the emperor Manuel I Comnenus.

The monastery fell on hard times later in the Ottoman period, but it withstood these difficulties through the support of the guild of the Greek linseed oil merchants in Istanbul and an endowment from the Feneriote nobleman Pascharnikos Christodoulos Vlachoutsis. Patriarch Gregory V lived there in 1809; the former patriarch Chrysanthos moved to the monastery when he retired in 1826 and died there eight years later. Patriarch Sophronius was in residence during the years 1866-70, and through his efforts the monastery was restored and the present katholikon completed in 1869, in accordance with plans drawn by the architect Vasilis Dimitriou.

What remains of the monastery are its katholikon and an adjacent two-storey wing on its south, as well as some out-buildings on the western part of its grounds. The katholikon preserves the carved wooden iconostasis from the earlier church, gilded and decorated with floral and plant designs in both low and high relief. The doors of the Oraia Pylai are particularly notable, with eight small icons in their panels, the most remarkable being a depiction of the Annunciation, all dating from the eighteenth century. There is also a fine eighteenth-century Offertory Diptych, with Christ in the traditional Deesis representation atop the panels, flanked by the Virgin and St. John the Baptist. Set into the south exterior wall there is a replica of an ancient Greek funerary relief, dating from the second half of the nineteenth century.