The monastery's association with imperial exile begins with the Byzantine practice of political mutilation: rather than execute a rival, emperors would have his eyes gouged out — a practice known in Byzantine culture that rendered the victim ineligible for the throne, since an emperor was expected to be physically whole. Romanos IV Diogenes, defeated at the Battle of Manzikert in 1071 in what proved to be a pivotal moment in Byzantine history, suffered this fate and was sent to Kınalıada to live out his days at the monastery. Before him, Emperor Nikephoros III Botaneiates (who ruled from 1078 to 1081) was also exiled here after being forced to abdicate. The monastery received these men not as prisoners in chains but as monks in decline — stripped of power, given the habit, left to contemplate what had been lost from a hilltop overlooking the sea.

The Ottoman conquest of Constantinople in 1453 was catastrophic for much of the Byzantine religious infrastructure, and the Monastery of the Transfiguration was no exception. It fell into a ruinous state in the years that followed. The recovery came in 1722, more than two and a half centuries later, driven not by imperial patronage but by private wealth: a group of prosperous Greek merchants from the island of Chios, then based in Constantinople, funded a major reconstruction. The restored monastery included a new katholikon — the main church of an Orthodox monastic complex — and a side chapel dedicated to Saint Paraskevi, built above the foundations of the original Byzantine structure. This layering of new construction over ancient remains is visible in the fabric of the building itself, though the reconstruction integrated the old and new into a coherent whole.

The monastery's influence extends beyond its hilltop walls. The bay on the northern half of Kınalıada is called Manastır Bay — Monastery Bay — named after the complex that has defined the island's northern skyline for centuries. From the water, approaching by ferry from Istanbul, the hillside rises clearly above the modest rooftops of the island's small town. The monastery sits at the peak, whitewashed walls catching the Marmara light. Travelers who make the walk up the hill — steep, unpaved in sections, worth every step — find the views across the archipelago reward the effort. On a clear day the Istanbul skyline is visible to the northwest, the Anatolian hills to the east.

The Monastery of the Transfiguration continues to attract visitors and pilgrims today. It appears in travel guides, including Frommer's Turkey, as one of the more historically significant sites on the Princes' Islands. The Greek Orthodox community that has maintained the monastery across these centuries is now much smaller than it once was — Istanbul's Greek population has contracted dramatically since the mid-20th century — but the monastery endures as both a religious site and a physical record of the Byzantine world that once organized this corner of the Mediterranean. Arriving here on a quiet weekday, when the ferries have taken most visitors to Büyükada and the island below is nearly empty, the silence of the hilltop feels genuinely ancient.