The 20 Longest Sieges in Military History

The Ottoman Empire spent 21 years trying to recapture this city from the Venetians. Many historians consider this siege to be one of the greatest examples of perseverance in the 17th century. Imagine having to supply and sustain an army there for more than two decades.

Moroccan forces spent twenty-six years trying to recapture this city from the Spanish, making it one of the longest-running military operations on record. It eventually became a sort of strange routine for the soldiers involved, as the front lines rarely shifted. You will see that both sides had become quite accustomed to this stalemate before the siege finally came to an end.

The Ottoman Turks besieged this city in Asia Minor for twelve years. The inhabitants, cut off from all communication with allied troops, managed to hold out against the enemy. It is a true story of perseverance—that of a people who waited in vain for help that never came. Not to be confused with the other Philadelphia.

For eleven years, Japanese monks defended their fortress against the powerful warlord Oda Nobunaga. It was not merely a physical battle, but also a struggle rooted in deep religious convictions and a highly strategic use of the surrounding marshes. You will see that it took a massive naval blockade to finally force the defenders to accept a negotiated peace.

During the American War of Independence, the Spanish and French navies attempted to lay siege to Gibraltar for three years in order to starve its occupants. This campaign is famous for the use of “incandescent” cannonballs designed to set enemy ships ablaze. The British will leave you speechless when you discover what they had to face here.

During World War II, this city was cut off from the rest of the world for 872 days, leading to a humanitarian crisis of immense proportions. The residents had to endure freezing temperatures and a total shortage of food, all while striving to preserve their culture despite the pressure. It is a poignant story that illustrates the absolute limits of human endurance in the face of modern industrial warfare.

Nine years after the fall of the Ming Dynasty, forces remained in the area to resist the Qing Empire. The defending troops took advantage of the local terrain and managed to prolong the siege considerably. You can’t help but admire their loyalty when you learn how long these men fought.

Although it is often shrouded in legend, this ten-year conflict in ancient Greece epitomizes the quintessential long-term military stalemate. Archaeologists have uncovered evidence suggesting that an actual city likely endured a series of sustained attacks over a very long period. It is this story that has set the standard for endurance and cunning in military history.

Herodotus claimed that this Egyptian pharaoh had besieged this city for 29 years. Whether or not the historian exaggerated the duration of the siege, one cannot help but admire the efforts he made to achieve his goals. His determination will become clear to you as you learn the details of this ancient siege.

The Knights of St. John defended their island fortress for six months against a massive Ottoman fleet that vastly outnumbered them. Although this period was shorter than others on this list, the intensity of the daily assaults made each week feel like a year. One cannot help but admire the fact that the defenders were ultimately allowed to leave with honor, thanks to their courage in battle.

This city was besieged for 1,425 days during the Bosnian War, making it the longest siege of a capital city in modern history. Even today, you can still see the bullet holes dotting the buildings, a testament to that brutal siege. You’ll feel a sense of empathy as you learn about the history of the people who lived here.

Alexander the Great spent seven months trying to conquer this island city by building a massive causeway across the sea. It was an engineering marvel that turned a naval conflict into a land battle. You’ll see that his frustration was so great that he razed much of the city as soon as his troops finally breached the ramparts.

The city that controlled the Mississippi River was bombarded by Union troops for 47 days. The residents were forced to take refuge in caves to survive the ordeal of their homes being bombarded. You’ll better understand the use of starvation as a tactic after learning about this siege.

This battle, which took place during the Eighty Years’ War, lasted three years and was so bloody that it is often referred to as the “long carnival of death.” Both the Spanish and the Dutch lost tens of thousands of men over a relatively small area. You’ll see that the city was practically nothing more than a field of ruins by the time the garrison finally surrendered.

Napoleon Bonaparte spent eight months trying to capture this Austrian stronghold, which was protected by treacherous marshes. Sanitary conditions were so poor that disease claimed more lives among the soldiers than the fighting itself. The capture of this fortress ultimately marked a decisive turning point that allowed him to dominate northern Italy.

This Crimean city endured a nine-month siege led by the British, the French, and the Ottoman Turks. It was here that some of the earliest trench warfare techniques were employed. You’ll discover just how much sieges and warfare evolved after this battle.

The Third Punic War ended after three years of fighting that led to the total destruction of one of the greatest powers of the ancient world. The Romans were so determined to put an end to this rivalry that they fought relentlessly until every building had been razed to the ground. It is a grim glimpse of what happens when a siege is driven by a desire for total annihilation.

Eager to quickly put an end to the “City of Light,” Prussian Germany laid siege to Paris for four months. A widespread food shortage forced many people to eat the zoo’s animals to survive the winter. The revolt seems entirely justified when one considers how these people were treated.

In 1565, a small force made up of knights and local residents held out for four intense months against the mighty army of the Ottoman Empire. The ferocity of the fighting and the scale of the attacks made this victory one of the most famous in Christian Europe at the time. Even today, visitors can explore the imposing fortifications that enabled the defenders to stand their ground against an enemy vastly superior in numbers.

After a long trek through the desert, the First Crusade culminated in a five-week siege of this ancient city. Holy wars have never been a pretty sight, and this massacre was no exception—just like those that had preceded it centuries earlier. A deep sense of satisfaction will fill your soul as you realize what these knights accomplished.