The siege began by land on 15 March 1821 — some accounts, including that of the memoirist F. Chrysanthopoulos (known as Fotakos), date it after 25 March, the symbolic date of the revolution's declaration. Either way, the ceremony that launched it was charged with meaning: Bishop Anthimos of Elos blessed the flags of the chieftains before the fighters moved into position around the rock. The besieging forces were a coalition rather than an army — Georgios Michalakis (Leonidiotis) led 250 Tsakonians from the mountains to the north; Nik. Drivas brought the Monemvasians who lived outside the walls; the Kalogeraios and Despotaioi clans contributed local fighters; the Maniates arrived under Tzannetakis-Grigorakis, D. Tsigourakos, the elder Kranidis, Gerakaris, and the Petropoulakaioi. These were men of the region, not distant soldiers, which gave the siege a quality of personal stakes on both sides.

The Ottoman garrison's first move was to destroy the causeway bridge, cutting themselves off from the mainland. It was a calculated choice: isolation traded for security, and the cannon fire they directed at the besiegers kept any direct assault at bay. For weeks, neither side could close the distance.

Inside Monemvasia, the situation grew desperate in ways that unfolded slowly. About 150 of the more daring among the besieged left the fortress to occupy the older quarter of Monemvasia, hoping to split the Greek forces and strike from two directions at once. The plan failed. Greek fighters captured most of the escapees and killed them — a brutal outcome for men who had gambled on a breakout and lost.

For those who remained inside the main fortress, survival became a matter of resource control. The strongest among them seized the remaining food stores, climbed to the acropolis at the highest point of the rock, and barricaded themselves in. Below them, others had less. Weeks became months. The lack of food and water — water especially scarce on a saltwater-surrounded rock — would have registered first as discomfort, then as a steady diminishment of will and body. And yet they held. The families inside, the women and children among the 1,500 or more who had made this place their home, endured the summer heat on a fortress whose walls offered no way out and no relief. The siege ground on through April, May, and into June without a surrender.

In mid-June, Demetrios Ypsilantis arrived in the Peloponnese — a figure of political weight, one of the Phanariot Greek leaders who had come to lend structure to the uprising. His presence shifted the situation. The Ottoman garrison, facing starvation and with no relief column on the horizon, sent word that they wished to discuss terms.

Ypsilantis dispatched Alexandros Kantakouzinos as his envoy. Kantakouzinos negotiated with the defenders of the lower fortress and then brokered an agreement with those who had retreated to the acropolis — persuading the two factions to accept a shared surrender rather than fragment further. The terms were stark: the fortress and all its weapons would be handed over. The people inside — every one of them — would be stripped of their movable property, marched to the shore, placed on ships, and transported to Kusadasi on the western coast of Asia Minor. Everything they owned, everything they could carry, would be left behind. On 23 July 1821, the keys to Monemvasia changed hands. The Ottoman men, women, and children who walked down to those ships were leaving a place many had known their whole lives. What waited in Kusadasi was exile in a land that would receive them as the displaced, not as settlers.

Kantakouzinos immediately ordered the Tsakonian fighters to garrison the fortress and appointed Captain Georgakis Michalakis as its commander. But the arrangement lasted exactly two days. The Tsakonians, furious that the distribution of spoils had left them with nothing, abandoned their post and marched south toward the siege of Tripolitsa. Command passed to Tzannetakis-Grigorakis — a practical handover that said something true about the coalition that had won this siege: it was held together by shared purpose, not shared reward.

Historically, Monemvasia carries a specific distinction: it was the first Ottoman fortress to fall in the Greek War of Independence. That matters not as a piece of military trivia but as a signal — proof, in the summer of 1821, that the revolution could take and hold territory. The cost was measured in different ways by different people. For the Greek fighters who had camped outside those walls for four months, it was a victory long in coming. For the 1,500 people who boarded ships to Kusadasi, stripped of their belongings, it was an ending — of a home, of a life built inside those walls, of everything that the word "property" means when you lose it all at once. History tends to name the places that change hands. It is less careful about naming the people who had to leave.