The Siege of St. Augustine, FL. 1702. Spanish Fort Unconquered. Delays British American Dominance.

Spain’s victory did more than just hold the line, it secured Florida as a critical bastion, shielding its Atlantic trade routes and standing as a barrier against the rising power of the American colonies. For decades to come, it would remain a Spanish stronghold, a thorn in the ambitions of an expanding America, a reminder that the old empire was not yet finished.

St. Augustine, FL. November 10 - December 29, 1702.
Spanish Forces: 230 Soldiers, 180 Indians and Freed African Slaves.
English Forces: 500 Soldiers, 300 Indians.

Additional Reading and Episode Research:

• National Park Service. Castillo de San Marcos.
• Arnade, Charles. The Siege of St. Augustine in 1702.

Transcript

Thanks for tuning in to this episode of History's Greatest Battles. Season 2, where we explore History's Greatest Sieges. If you know anybody that enjoys this genre of history, please share the podcast with them.

In the early 18th century, the struggle for North America was not yet decided. Spain, once the dominant power in the New World, found itself locked in an unrelenting contest with England. The Caribbean was a battleground. The eastern seaboard of North America was a frontier in dispute. The balance of power between empires was shifting, and no nation could afford to lose ground.

Spain’s hold on Florida had never been secure. Isolated from the wealth and reinforcements of Mexico, it was a vulnerable outpost in a vast, contested land. To the north, the English colonies of Carolina and Georgia were expanding, their populations growing, their ambitions unchecked. These were not simply settlers, they were frontiersmen, traders, and soldiers, men who saw Spanish Florida as an obstacle to be removed. With war raging in Europe, England’s colonial leaders seized their chance to drive Spain from the continent, striking deep into the heart of its last northern stronghold.

The siege that followed was not just a battle over a distant Spanish outpost. It was a test of endurance, of military strategy, of the sheer will to hold or to conquer. Its outcome would determine whether Spain could maintain a presence in the region or whether the English advance would continue unchecked. The consequences would stretch far beyond the battlefield. Had the fortress fallen, Spain’s grip on Florida could have been severed decades earlier. England’s hold on the Southeast could have solidified, tightening the noose around France’s Louisiana and Spanish Mexico. The American colonies, still a century from revolution, would have grown under an even stronger English hand, altering the shape of the future United States.

Instead, the fortress held. Spain remained entrenched in Florida, a thorn in England’s side, complicating British control over its southern frontier for another century. When the American Revolution came, Florida was still Spanish territory, forcing the British to fight on yet another front. And when the United States emerged, its expansion into the South was delayed, reshaped by the stubborn endurance of a Spanish stronghold that refused to fall when it mattered most.

This was more than a siege. It was a moment where the fate of a continent wavered, where the ambitions of empires collided, and where the future of North America took a path that few could have foreseen.

Let’s now experience, the Siege of St. Augustine.

When Columbus set sail in 1492, he cracked open the door to a new world, and Spain wasted no time forcing it wide open. The islands of the Caribbean became the first prizes in an empire that would soon stretch deep into the heart of the Americas. With ruthless efficiency, Spanish conquistadors carved their way through Central and South America, tearing the riches of the Aztec and Inca empires from their fallen hands. Gold, silver, and jewels poured into Spain’s treasury, fueling a kingdom that now strode the world like a colossus.

The wealth of the Spanish Empire was irresistible, and by 1522, rival European powers smelled opportunity. They would not build their own empires just yet, but they would bleed Spain dry if they could. Raiders, privateers, and outright pirates took to the seas, hunting Spanish treasure ships like wolves chasing a fattened stag. Spain struck back. The Florida peninsula became a vital chess piece in their defense of the Caribbean, a natural barrier against marauders. Anchoring their power in Havana, they planted their flag in Florida, determined to hold it against any who dared threaten their empire’s lifeline.

When the French made their move in 1564, daring to claim northern Florida, Spain reacted with unshakable resolve. They planted their own men at St. Augustine, not just to drive out the French interlopers, but to bring the land fully under Spanish dominion, its people, its resources, its soul. Nine times, the Spanish built wooden forts to hold St. Augustine. Nine times, they were reduced to splinters, shattered by enemy assaults, battered by storms, or devoured by the relentless gnawing of insects. For decades, Spain thought wood would be enough. But in 1665, as English settlers clawed southward and pirates grew bolder, it became clear, timber would no longer cut it.

The English weren’t just settling the land, they were raiding, burning, plundering. The Caribbean had become a hunting ground for British pirates, and if Spain wanted to keep its northern flank intact, it needed something more than a wooden barricade. It needed stone. The breaking point came in 1668. English attackers reduced the last wooden fort to cinders, and Spain had had enough. The monarchy answered with cold determination, St. Augustine would not fall again. They would build a fortress that could withstand cannon fire, siege, and time itself.

The answer lay in coquina, a stone found in Florida itself. Soft and damp when quarried, it hardened over time, refusing to shatter under bombardment. Cannonballs didn’t break it, they sank into it. The fortress would stand, no matter how fierce the assault. Work began in August 1671, but the fortress rose slowly, too slowly for comfort. Costs soared. Timetables stretched. By the time it was finally completed in 1695, it had cost more than double the original estimate. But what they built was no mere outpost. It was a statement: St. Augustine would never fall easily.

For twenty-four years, as stone by stone the Castillo de San Marcos rose, the frontier seethed with hostility. Spanish Florida and English Carolina stood like two predators circling each other, neither willing to back down. Skirmishes erupted in the dense wilderness, each side testing the other’s resolve. The battles weren’t just fought in the shadows of the forests. English colonists and pirates made their intentions clear, striking at St. Augustine itself. Each attack was a warning, without a true fortress, the town was vulnerable.

The fort’s walls stood defiant, thick and unyielding, but atop them, its artillery was another matter. The cannons were relics of an earlier age, barely fit for war. Governor José de Zúñiga y Cerda knew that a fortress without proper guns was a target waiting to be struck. He sent word to Spain, demanding modern firepower. But he was not the only man with plans. Governor James Moore of Carolina saw an opportunity, attack before the Spanish could arm themselves.

War had erupted in Europe, the War of the Spanish Succession, and its flames licked across the Atlantic. In Carolina, Governor Moore moved fast. He gathered 500 colonial militia and 300 Yamasee warriors, their loyalty bought with the promise of plunder. The Carolina legislature did not hesitate. Spain and England were at war. Their colonies would be too.

On October 16, 1702, Charleston’s harbor churned with war. Fourteen ships cut through the water, carrying Moore’s forces south. His plan was simple: he would strike by sea while his lieutenant, Colonel Robert Daniel, led a land force to descend upon St. Augustine from the north. The Spanish would have nowhere to run.

Daniel’s force made landfall in Spanish Guale on November 3. There would be no mercy. Villages burned, their inhabitants either slain, captured, or fleeing south in desperation. The road to St. Augustine lay open. Meanwhile, Moore’s men carved their own bloody path along the coast. By the evening of November 4, the survivors of both assaults staggered into St. Augustine, breathless and terrified. War had come.

Zúñiga wasted no time. The town’s people were ordered inside the fortress walls. Every scrap of food was seized. St. Augustine would not fall for lack of preparation. Desperate, Zúñiga sent a frigate slicing through the waves to Havana, pleading for reinforcements. Messengers rode hard to Pensacola and Mobile, carrying the same urgent call: come now, or come too late. He was not content to simply wait. A small Spanish force rode north to blunt the English advance. They fought, they bled, but they could not halt the tide.

By nightfall on November 5, the first English ships loomed on the horizon, nine miles from the town. At dawn, three of them cut south past St. Augustine, sealing the Matanzas Inlet, their grip on the city tightened. By November 8, Moore’s fleet had reached St. Augustine’s harbor. But the sea itself conspired against him, the waters were too shallow for his ships to breach the entrance. Undeterred, his men landed on the southern shore and moved inland, linking up with Daniel’s force. The siege was about to begin in full.

On November 9, Zúñiga gave his final order, every last citizen was to take refuge within the fortress. No more would be left outside the walls. By morning, his scouts brought grim news: Daniel’s men were nearly upon them. The English swarmed into St. Augustine, seizing every street, every alley, every building that lay beyond the fortress walls. Once their foothold was secured, Moore landed his own force, reinforcing the noose that was tightening around the Spanish stronghold.

Within the stone walls of the Castillo de San Marcos, Zúñiga commanded roughly 1,500 souls. Among them, just over 200 were trained soldiers, with another 400 civilians he could press into service. It wasn’t enough. His cannons were relics, his ammunition scarce, and his gunners had never faced a real siege. The fortress was strong, but its defenders were another question entirely. Captured prisoners revealed the grim truth: the English were prepared to starve St. Augustine into submission. They had supplies for three long months. Zúñiga knew his own stores wouldn’t last nearly that long. If help didn’t come from Havana, the fortress would fall.

By November 14, the English held St. Augustine itself. But Zúñiga refused to let them turn the town into a base for their siege. He ordered a daring sortie, Spanish troops surged from the gates, torches in hand, and reduced every house within musket range to charred ruins. The English would find no shelter here. Every building within 75 yards was wiped from existence. Now, nothing stood between the fortress and its enemies, only open ground, where Spanish muskets could cut down any who dared approach.

Moore’s men lacked the heavy guns to breach the walls outright. So they turned to the old method, trenches. They clawed at the earth, digging their way forward, inch by inch, determined to bring their limited artillery close enough to strike. The Spanish guns roared from the parapets, but their fire did little real damage. Still, it kept the English hunched low in their trenches, wary of exposing themselves to a well-placed shot. Moore had a plan. His men were buying time, time for heavier artillery to arrive from Jamaica. He sent Colonel Daniel south, ordering him to return with the firepower needed to bring the Castillo de San Marcos crumbling down.

The siege became a battle of patience and endurance. Zúñiga, against all odds, managed to slip messengers past the English lines. His pleas for help raced through the wilderness and across the sea, but whether they would be answered remained unknown.

On December 14, a man calling himself Juan Lorenzo appeared at the gates of the fortress. A native, accompanied by his wife, claiming to have abandoned the English. Once inside, he spun his tale, he had defected, abandoning the English out of loyalty to the Spanish cause. He came bearing what Zúñiga most wanted to hear: the English were growing desperate. Their resolve was cracking. Soon, they would break. But Lorenzo was not what he seemed. Once placed among the other natives within the walls, he whispered of rebellion.

Word of his treachery reached Zúñiga swiftly. Lorenzo was seized, dragged away, and subjected to interrogation that left no room for deception. He refused to break. But his wife did. Under pressure, she revealed the truth, Lorenzo had been sent by the English with a mission of sabotage. If he had succeeded, the fort’s powder magazine would have been destroyed in a fiery explosion.

By December 19, the English had clawed their way within 100 yards of the fortress. But it wasn’t enough. They still lacked the firepower to tear through the stone walls that stood between them and victory.

Then, on Christmas Eve, Spanish hearts sank. On the horizon, two ships appeared, and above them, the Union Jack snapped in the wind. But the ships did not bring what Moore had hoped for. No great siege guns from Jamaica. Only more men, more powder, more provisions to drag out the siege.

Zúñiga refused to let despair take hold. He ordered a Christmas celebration, handed out bonuses to his men, anything to keep their spirits from collapsing under the weight of the siege. It wasn’t enough. But two days later, salvation arrived. Four Spanish warships cut through the waters offshore, their banners flying.

The Spanish ships lingered offshore, their captains cautious, unwilling to rush into battle unprepared. For days, they held their position, while inside the fortress, Zúñiga and his men waited, desperate for action. Then, on December 29, the waiting ended. Spanish troops, 212 hardened men, disembarked just down the coast, ready to turn the tide.

Moore had seen enough. His gamble had failed. He could not storm the fortress, and now fresh Spanish troops threatened his rear. The only path left was retreat. But retreating wouldn’t be easy. The Spanish ships had cut off his escape by sea, leaving him no choice. He gave the order, his own fleet was to be burned, reduced to ashes to keep it from falling into enemy hands. His men would march north, back to Carolina, through the very wilderness they had come to conquer.

Fortune had not abandoned him entirely. Reserve ships, hidden farther up the coast, waited like lifelines. The retreating force reached them, and one by one, Moore’s battered men climbed aboard, escaping Spanish vengeance by the narrowest of margins.

As Moore’s force withdrew, they left behind a final act of destruction. St. Augustine was set ablaze, flames licking at the remnants of Spain’s northern outpost. But when Zúñiga and his men reentered the town on December 30, they moved swiftly to control the fires. The city would not be lost.

The battle was won, but victory came at a cost. St. Augustine lay in ruins. It would take years to rebuild, but rebuild they would. Moore’s campaign had left a scar. The Spanish outposts at Apalache, Timuca, and Guale were gone, wiped from the map. St. Augustine now stood alone, the last Spanish stronghold in northern Florida. Over the next two decades, they reinforced it, enclosing the town with a wall, determined that it would never again stand so vulnerable.

But the English were not done. They had failed to take St. Augustine, but they had not given up on Florida. Even after the War of the Spanish Succession officially ended in 1713, the guns never truly fell silent.

In 1728, Colonel William Palmer led yet another English force south, marching on St. Augustine. But when he saw the Castillo de San Marcos standing as defiant as ever, he hesitated. He withdrew without firing a shot. But the English were not done testing the fortress. The last great siege came in 1740, led by James Oglethorpe himself, the founder of Georgia. He aimed to break Spanish power once and for all, securing his own colony’s southern flank.

Spanish Governor Manuel de Montiano knew the key to victory: strike before the enemy could consolidate. He launched a bold sortie, hitting the English while they were still divided. The attack threw Oglethorpe’s plan into chaos. Furious but undeterred, Oglethorpe’s forces unleashed a relentless bombardment. For twenty-seven days, naval guns hammered the fortress, but the Castillo de San Marcos did not break. The walls absorbed the cannonballs, the defenders held their ground, and casualties remained light.

The siege dragged on, and then nature itself turned against the English. Hurricane season loomed, threatening to trap Oglethorpe’s men in an unwinnable fight. Faced with the impossible, he made his choice, retreat to Georgia, leaving the fortress unconquered.

The Castillo de San Marcos had proven itself. When the last cannon fell silent, it had done exactly what it was built to do: stand unbroken. Every enemy that had tried to take it had failed. Spain still ruled northern Florida.

By 1762, the Spanish made their final improvements to the fortress. But its days of war were over. No enemy would challenge its walls again. Oglethorpe had been the last. And then, in 1763, Spain’s grip on Florida slipped, not through war, but through diplomacy. As part of the treaty that ended the Seven Years’ War, they ceded Florida to the British. But the wheel of history kept turning. After the American Revolution, Spain reclaimed its lost province once more.

Spain’s second reign over Florida would not last forever. By 1819, with its empire fading, Spain sold the territory to the United States. The torch had passed.

By then, the Spanish Empire, an empire that had once bent continents to its will, that had filled its coffers with the wealth of fallen civilizations, that had ruled the seas with an iron fist, was little more than a fading echo. The banners that once flew over half the known world were now tattered relics of a past that had slipped beyond Spain’s grasp. Its armies had marched, its kings had decreed, its fleets had conquered, but time had conquered Spain in turn. And as its grip loosened, another force rose in its place. The United States was not simply inheriting the remnants of an old world, it was forging an entirely new one, a power unlike anything history had ever known. The Castillo de San Marcos still stood, its walls scarred but unbroken, a silent witness to the unrelenting cycle of empires. Stone does not weep, but if it could, it would mourn the mighty who built it, only to be forgotten. Because this is the truth carved into its very foundations: no kingdom endures forever, no empire is safe from time, and the rise of one is always the funeral toll of another.