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Guided tour of El Morro Castle in Old San Juan. Learn about its history with three immersive audio recreations of this fort’s most important battles: the 1595 British attack led by Francis Drake, the 1598 British attack by the Earl of Cumberland and the 1625 Dutch takeover of the city.
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Audio Guide Transcript: El Morro in Three Epic Battles
Welcome to this Free Audio Guide to El Morro. FreeAudioGuides.com delivers the best and most immersive tours of your favorite travel destinations, in a podcast format, always free, with nothing to rent and no app to download.
My name is Lara and my name is Armando, and we are your local guides. Today, we’re taking you and your family to El Morro Castle, on a trip through 500 years of history.
You can do the tour at your own pace, but we estimate that at a normal walking clip it should take you about an hour to get from site to site and enjoy the audio content we’ve prepared for each stop along the tour.
To navigate your way through this tour, please pick up the helpful free map provided by the National Park Service for the San Juan National Historic Site. It’s available right as you enter the fort past the Park Ranger’s desk. We’ll be referencing the inset map titled “Castillo San Felipe del Morro”, which has the six levels of the fort clearly labeled, and we’ll play this sound ____ whenever we suggest you pause the podcast to make your way to the next location. We’ve also included a link to the map in the episode description for this tour.
By the way, Park Rangers are super friendly and super knowledgeable, so if you have any questions, reach out to one of them.
Our podcasts are also divided into chapters. Many podcast apps, like Apple Podcasts and Overcast support this feature. Each level of the fort has its own title and chapter, allowing you to quickly browse, skip ahead and navigate directly to different sections of the guide.
Once you’re done with this tour, be sure to check out our other podcast tours, at puertorico.freeaudioguides.com for locations like San Cristobal Castle and the Puerto Rico Art Museum, and our weekly podcast, Puerto Rico Now, available on this same feed, where we’ll give you locals’ access to everything happening while you’re here visiting the island. Find out about the most exciting parties, festivals, free events, new restaurants and family-friendly gatherings going on right now, this very week, in Puerto Rico.
To help us grow, please leave us a five star review on your podcast app of choice, subscribe to the show, follow us on Twitter, Facebook and Instagram as FreeAudioGuides, and be sure to support our advertisers. If you want to go a step further, you can show us, your tour guides, some love at our virtual tip jar at puertorico.freeaudioguides.com. We’ve also placed a link to the tip jar in the show notes.
Now, let’s get started!
If you just entered the fort, you’re at one of its highest levels, labeled number five on the map. This is the Main Plaza. This tour will take us from the oldest part of the fort, which happens to be the bottommost part, back up to where we are now. As we make our way up through the fort’s different levels, we’ll be traveling forward in time and, along the way, meeting this site’s most important historical figures.
Let’s start heading down to the Water Battery. This part of the fort can sometimes be closed, so ask a Park Ranger if the Water Battery is open on the day of your visit.
If the Water Battery is open, head to the level labeled with the number one on your map. If it’s closed, head to the observation deck on level four. From there, you can look down onto the Water Battery.
As you walk to our first stop on the tour, let’s get you up to speed on a little history.
Puerto Rico had been inhabited for thousands of years by indigenous peoples. At the time of Columbus’s arrival in 1493, during his second voyage to the Americas, the local population, known to history as Taínos, called the island Boriquén, loosely translated as "the lands of the valiant and noble lords”. The modern term for Puerto Ricans, “boricua”, is a derivative of the original, “Boriquén”.
The Spanish monarchs laid claim to the island and in 1508 granted Juan Ponce de León permission to explore and colonize the territory. In the ensuing decades, the naturally well-protected bay on which El Morro is built became of strategic importance to Spanish transatlantic trade. Puerto Rico’s geographic location and access to fresh water made it the first good harbor for ships coming to the Americas from Europe after the months-long voyage. The trade winds, required to propel ships back and forth across the vast Atlantic, would naturally deposit incoming vessels in its vicinity and sailors would disembark to resupply.
This made Puerto Rico a hugely important asset in a complex network that defended the merchant fleet and its trade routes, and particularly the transportation to the Old World of gold, silver and gems extracted from Spain’s American colonies. All this treasure making its way around the Caribbean attracted… what else… pirates. Lots and lots of pirates.
The impressive fortifications you’re in now, the old walls around San Juan, San Cristobal Castle and a number of other smaller forts and batteries, were built to defend against the pirate threat and, crucially, against rival countries’ designs on the Caribbean. Late to the game, other European powers wanted to build their own New World empires, and Puerto Rico became an attractive piece in the high-stakes diplomatic - and not so diplomatic - game to control American treasure.
Let’s take a break here. Once you get to our first tour location, press play and we’ll take you back to the sixteenth century.
Welcome back. The Water Battery is the platform jutting out toward the bay from the massive fort behind you. Take a look around… let’s get oriented.
If you’re looking out toward the water, the fort is to your back. The fort itself would have been much smaller in the sixteenth century. All that existed of El Morro was the Water Battery and a round medieval tower that was eventually enclosed in later efforts to expand the fort. The interior of the tower, much in its original form, is still accessible, and we’ll spend time there in the next section of this guide.
The fort’s construction began in 1539. The site was chosen because of its naturally occurring advantages. Not only is it at the entrance to the bay but it is also a massive 120 foot cliff projecting out into it.
Throughout the centuries, the fort was built by artisans, carpenters, blacksmiths and sculptors, and also slaves and prisoners condemned to hard labor. Iron is presumed to have been imported from Spain, but much of the rest of the construction materials was sourced locally. Stones mined from island quarries were bound together with mortar made up of lime, and both beach and pit sand.
Toward the end of the sixteenth century, construction had been completed on the tower and the Water Battery, and additional improvements had been made to the fort’s defenses on the landward side.
These original fortifications were first put to the test in 1595 by the Dread Pirate Francis Drake.
Speaking of which, the term “pirate” can be misleading. Some pirates were, more precisely, corsairs or privateers. These private individuals, as the name implies, were given a commission by a state to attack and capture the ships of an enemy state. Such was the case with Francis Drake, who plied the seas under the auspices of Queen Elizabeth the first of England.
Francis Drake was, at the time of his attack on this fort, famous the world over. His enemies feared and respected him. The latinized version of his name, draco, means dragon, and added to his myth. To the British, he was a hero; the queen had awarded him a knighthood in 1581.
Drake’s primary objective was the capture of a large treasure of about 5 tons of gold and silver from a Spanish ship, the Begoña, which had suffered damage at sea as it embarked on the return voyage to Spain. The ship was in San Juan harbor for repairs and the treasure had been transferred for safekeeping to the nearby La Fortaleza, the present-day governor’s mansion.
At the behest of Queen Elizabeth, a fleet of six royal galleons and twenty-one private vessels set out late in the month of August 1595, Drake at the helm of his flagship, the Defiance. The Spanish caught wind of his plans and were able to bolster San Juan’s defenses in anticipation of his arrival. Five frigates, dispatched by King Phillip the second of Spain to retrieve his treasure, had managed to arrive in San Juan, reinforcing the local garrison with an additional 250 soldiers, and 300 sailors and gunners.
On November twenty second, 1595, Drake’s fleet was sighted and dropped anchor three miles east of where we stand now. Overconfident, Drake sat down to supper with his officers. Traveling with the famed seafarer was Thomas Maynarde, a relative of Drake’s by marriage, who wrote an account of the events that transpired.
“The enemy labored by all means to cause us to disanchor. Within an hour he had planted three or four pieces of artillery upon the shore next to us. While our generals sat at supper, a shot came amongst them, wherewith Sir Nicholas Clifford, Brute Browne, Captain Stafford, and some standers by were hurt… Sir Nicholas died that night… Brown lived 5 or 6 days after and then died.”
Some say Drake’s own stool was shot out from under him as he took a long swig from a large flagon of beer.
Meanwhile, in El Morro, defensive preparations had been completed. Twenty-seven bronze cannon were mounted on the Water Battery. Two Spanish ships, including the Begoña, were sunk at the mouth of the bay between where you stand now and Isla de Cabras, the island visible from here by looking west across the harbor. These hulks limited access to the bay to a narrow channel between El Morro and the nearest sunken ship, thereby improving the fort’s defensive capabilities and the reach of its cannons. Behind this blockage, the Spanish lined up the five frigates that had arrived from Europe.
After receiving reports on Spanish defenses, Drake concluded that trying to force his way into the bay with his larger ships, and so little room to maneuver, would be too risky a tactic. Imagine how easy it would have been for the Spanish, so close to sea level on the Water Battery, to fire their cannons into the sides of incoming English galleons.
And so, Drake planned a daring attack. He first moved his fleet just off shore Isla de Cabras - the masts of his ships bobbing up and down in the rough Atlantic waters would have been visible from here. On the night of November the twenty-third, at 10 o’clock, Drake dispatched his men in about thirty canoes under the cover of darkness. At first, the Spanish were hampered in their response. The smaller vessels were able to get so close to this fort, that the Spanish could not aim the cannons low enough to hit the nearest boats. Still, the English came under heavy fire from El Morro.
Bypassing land defenses, the canoes clustered around the Spanish frigates and from there the attackers hurled fireballs and other incendiary material into four of them. Crews onboard were able to put the fires out but, on a third attempt, the blaze took hold at the stern of a ship by the name, Magdalena, and grew out of control. The fighting continued for another hour, but what advantage the English might have had at first by attacking at night, had been squandered as the great fire lit the night.
Thomas Maynarde, who led the attack, provides us with details of the battle.
“The burnt ship gave a great light, the enemy thereby firing upon us with their ordinance and small shot as if it had been daylight out, sinking some of our boats. A man could hardly command his mariners to row, they foolishly thinking every place more dangerous than where they were.”
The result was a resounding victory for the defenders, but not without its costs. Spanish sources say eight to ten English craft were sunk and somewhere between 200 and 400 of Drake’s men, lost. According to English sources, Spanish casualties were higher still.
After a half-hearted attempt at rushing through Spanish defenses, Drake and his fleet weighed anchor and sailed away from San Juan on November twenty-fifth.
The defenses of El Morro, combined with a much smaller force of only five Spanish frigates, had been able to fend off an attack by twenty-seven English ships. The treasure was in Spanish hands and would soon be transported to Europe.
Drake would die, barely two months later, in 1596, during his last, and ultimately failed attack, on Panama. He was buried at sea, wearing his armor.
Let’s take a break here. Feel free to walk around and explore on your own in between our stops. Getting lost in this amazing historic site is half the fun.
When you’re ready to continue the tour, head to the old tower, labeled with the number two on your map. Once you’re there, press play on your podcast app.
Welcome back. You are now inside the oldest part of the fort, the old tower. As we indicated earlier, the tower was eventually enclosed by the growing fort around it, but the interior survived.
Despite the successful defense against Drake in 1595, the Spanish monarchy rightly considered San Juan vulnerable to future attacks but did little to improve the city’s defenses in the intervening years. In fact, things got worse. Low on funds, and ravaged by hunger and disease, the military garrison was down to barely 176 soldiers three years later.
Under these dire conditions, the city would again be attacked by an English expeditionary force. At the head of a powerful fleet of twenty-one vessels crossing the Atlantic in the spring of 1598, was Sir George Clifford, the third earl of Cumberland, commanding his flagship, the Scourge of Malice. Queen Elizabeth’s orders were to capture San Juan, which with its secure and defensible port, would provide the English with an excellent base of operations for privateering and for the expansion of their New World holdings. Cumberland himself, who wrote an account of his voyage in a letter to the Queen, called Puerto Rico, “the keys of all the Indies”.
Trying to avoid Drake’s mistakes in attacking the well defended mouth of the bay, on June the 16th, Cumberland landed about a thousand of his men on Condado beach and marched them to the fortified San Antonio bridge. This crossing connected, as a more modern structure does to this day, the island on which Old San Juan sits and the larger island of Puerto Rico.
After attacking a small fort that defended the bridge and that the Spanish called “Matadiablo”, or Devil Killer, as it was from there Drake’s flagship had been successfully fired upon, the English marched unopposed into San Juan. Defending soldiers had left the city proper and had holed up here, in El Morro. Initially, the Spanish governor refused to surrender and so, Cumberland began a siege of El Morro, blocking any attempt at resupplying those trapped within with food and water.
Cumberland ordered the fort be bombed. Sheltering inside this tower, the few remaining Spanish soldiers, hungry, thirsty and fearing for their lives, huddled in the dark as the English hit the fort with artillery. In a few days, the Spanish were ready to talk terms of surrender. After Cumberland assured the Spanish governor of safe passage for his soldiers, the two sides made peace over dinner. The Reverend John Layfield, chaplain of the English fleet, takes us inside the room where it happened…
“That day the Governor and his company dined with his Lordship Cumberland, and after dinner, the Governor went and brought his companies out of the Fort and delivered the keys to his lordship, who immediately brought in his own colors and placed them upon the fort.”
The siege had lasted under two weeks. By July the first, the English flag flew over El Morro. The occupation, however, would not last. Though Cumberland was intent on holding the city, dysentery afflicted his troops. In just weeks, 400 of his men would die and another 400 lay ill. His able soldiers down to 700 and knowing the Spanish were readying a fleet to retake the city, the English set sail from Puerto Rico but not without first sacking and burning much of the city. The seventeenth century would dawn with a nearly defenseless San Juan attempting to rebuild.
Before we move on, we will take a short historical detour. If you’re standing in the tower looking toward the ramp leading to the upper levels of the fort, look up and to your left. There you’ll see a projectile lodged in the wall. It was driven into the fort on May the 12th, 1898, 300 years after Cumberland’s siege of El Morro, by the United States naval fleet under the command of Admiral William T. Sampson.
On that day, Spanish and Puerto Rican soldiers fought valiantly in this fort, built to defend against galleons, bombarded now by modern battleships - two different eras clashing. Unlike the English, the Americans would eventually take Puerto Rico and hold it to this day.
Let’s move on from here. Feel free to explore the level labeled with the number three on your own. Be sure not to miss the kitchen where meals where prepared for Spanish soldiers and the forge where they did their metalwork. The walls are stained with soot from those hot fires centuries ago.
When you’re ready, head to the fourth level. You can take the stairs leading up to the main ramp or you can use the circular staircase which provided soldiers with faster access between the two levels in the heat of battle. Once you’re on the fourth level, press play on your podcast app to continue the tour.
Welcome back. This fourth level of the fort affords one of the best views of the mouth of San Juan bay from the observation deck. Be sure to check it out.
Right by the observation deck is a sentry box, or “garita” in Spanish. Soldiers would be posted here to look for enemy ships. One sentry box in particular, in San Cristobal Castle, is known to every single Puerto Rican as part of local legend, “la garita del diablo”, the devil’s sentry box. It is said this particular post was so far from the fort, that soldier’s feared being sent there on duty. One night, a soldier by the name of Sánchez, disappeared, leaving behind only his uniform and his weapon, never to be heard from again. The sentry box has had its cursed name until present day.
If you look up from here toward El Morro’s three flags, you’ll see a more modern observation post, with a smooth curved surface and three large slits. Clearly, this isn’t colonial Spanish architecture. In fact, it was built into the fort during World War II. From here, American soldiers would watch for German submarines and other warships.
A note about the flags: you’ll probably recognize the Puerto Rican flag and the American flag. Puerto Rico is a United States commonwealth or territory, and hence, The Stars and Stripes fly over public buildings here. The third flag, however, may be unfamiliar to you. It is the Burgundy Cross, the Spanish military flag during most of the colonial era.
Let’s head up to the fifth level. Here again you have two options. You can take the stairs by the main ramp or the more quaint triangular stairs. Once you’re back on the fifth level, you’ll be in the Main Plaza. Head over to the chapel, where you can sit and take a quiet break away from the sun and the crowds, and press play once you’re there.
Welcome back. One of Spain’s main goals in colonizing the Americas was taking Catholicism wherever she went. The life of a Spanish soldier included daily mass at this chapel. Before major battles, soldiers would gather here to pray for good fortune, or to confess their sins should they perish in combat. Back then, mass was in Latin. Imagine the fort’s hundreds of soldiers pouring out into the Main Plaza, enemy ships bearing down on them, the mood grim…
“Pater noster, qui es in caelis,
sanctificetur nomen tuum.
Adveniat regnum tuum.
Fiat voluntas tua,
sicut in caelo, et in terra.”
If they weren’t off to battle, after mass, soldiers would have headed back to their living quarters. You can see a recreation of these rooms, and their not so comfortable sleeping arrangements on this level. If you’re leaving the chapel, they’ll be off to your right.
You can check out the prison by crossing straight from the chapel over to the other side of the plaza, to the right of the public restrooms. A gunpowder magazine where cannonballs and other weapons were kept is to your left as you leave the chapel, near the ramp heading up to the sixth and final level.
Once you’re ready, head to the sixth level by taking that ramp next to the gunpowder magazine. Once you’re at the top of the ramp, press play on your podcast app and we’ll finish up today reliving this fort’s greatest battle, the 1625 Dutch attack on San Juan.
Welcome back. You are now standing on the Austria Bastion. By 1625, this section of the fort, and the dry moat below, had been built. Their purpose was the defense of the fort’s land side, with cannons pointing through the openings on the walls toward the large green esplanade you crossed to get to El Morro. The fort had taken on the basic shape it retains to this day. However, the rest of the city was undefended, with no walls protecting its sea and harbor sides, and the city proper vulnerable to a land attack similar to Cumberland’s in 1598.
In 1625, the Dutch would attempt just such an attack. Under the direction of the privateer Boudewijn Hendricksz, a fleet of seventeen ships and over 2,000 men, appeared on the horizon. Catching the city by surprise and woefully unprepared, Puerto Rico’s new governor, Juan de Haro, who had been on the job less than a month, made urgent defensive arrangements.
On September the 25th, with favorable winds, and betting El Morro’s cannons could inflict some harm but not keep the entire fleet out, the Dutch sailed into the harbor and dropped anchor close to where cruise ships dock in present day San Juan. Though El Morro’s cannons did fire on the invaders, the Spanish soldiers were not well-trained artillerymen and their equipment kept malfunctioning. Hendricksz’s bet had paid off. He’d taken the bay at the cost of only four of his men.
From there, the Dutch disembarked and marched into the city essentially unopposed. Governor de Haro, knowing his much smaller garrison would not be able to face off out in the open against the much larger enemy force, retreated into El Morro with about 330 soldiers and what limited provisions they’d been able to gather. Brave locals would aid the soldiers, rowing canoes past the Dutch blockade and directly to the Water Battery, where they would hand off supplies to the men inside the fort.
Hendricksz meanwhile set up his headquarters at La Fortaleza, and a foreign flag again flew over the city. From there, he wrote the Governor, and ordered him to surrender the fort or else he would take it and kill all who opposed him, even the elderly, women and children. From within El Morro, de Haro responded that he would do no such thing, and the Dutch began a siege of the fort.
To imagine the siege, look out through the openings on the fort’s walls onto the green lawn. On the far end, the Dutch began digging trenches. From there, artillerymen fired their cannons on El Morro. Dutch “sappers”, or diggers, continued building trenches that came ever closer to the fort. With each line of attack getting nearer, the Dutch continued firing with greater precision, exacting casualties and weakening Spanish defenses. The invaders would dig over 3,300 feet of trenches in this field.
However, the Spanish responded with their own cannons and with daring raids wherein soldiers would exit the fort, jump in the trenches and engage in hand to hand combat with the Dutch.
A Spanish official, Diego de Larrasa, wrote of these courageous attacks:
“At nine in the morning, our soldiers on the Austria bastion, alerted the Governor that the enemy was approaching through the trenches with a large piece of artillery, and that they were nearing our moat. The Governor ordered that his soldiers on the bastion respond with cannon fire, and they successfully destroyed the incoming enemy artillery and killed eight of their men. Encouraged, at noon he ordered captain Juan de Amézquita to lead fifty men outside of the fort and attack the enemy lines, which they did with such enthusiasm and effort that they injured and killed more than sixty men, among them a captain and a sergeant major, and we lost not a single man.”
The Dutch would lob 4,000 cannon balls at the fort, but after three weeks, were no closer to taking El Morro. With Dutch losses mounting - Spanish estimates put the number of enemy dead at over 400 - Hendrick’s sent one last ultimatum, surrender or we burn the city. De Haro again refused to budge. Good on his word, before sailing off, Hendricks ordered his men to carry off anything of value and to torch the town, reducing nearly one hundred buildings, including La Fortaleza, to ashes.
This traumatic, and yet, heroic experience would finally convince the Spanish monarchy of the need to fortify the entire city. Within 25 years, San Juan would be encircled by walls and construction would begin on San Cristobal Castle. Both were designed to prevent a repeat of the Dutch takeover of the city by land. If you're interested in this topic, we’ll continue covering it on our FreeAudioGuides.com podcast tour of San Cristobal Castle, available on this same feed.
On this sixth level, you can also see the fort’s lighthouse. You’ll notice its architecture is unlike that of the rest of the fort. El Morro has had three lighthouses. American engineers built the current structure on the foundation of an earlier Spanish lighthouse which was destroyed during Sampson’s bombardment of San Juan in 1898.
As we wrap up, look out again onto the great green expanse in front of the fort. This is a field laden with memories, individual and collective. About halfway between the fort and the rest of the city, to the right of the walking path, there is a monument erected to honor Captain Amézquita and the rest of the soldiers who defended San Juan in 1625. After the US invasion, El Morro became known as Fort Brooke, and for fifty years, was off limits to civilians. The lawn you see before you was a golf course for military officers. In 1949, El Morro was transferred to the National Park Service and in 1983, it, along with La Fortaleza, was designated a UNESCO World Heritage Site.
Today, there are likely dozens of kites flying overhead. Coming here and flying your first kite is a rite of passage for Puerto Rican children. This place, in which so many Spanish and Puerto Rican soldiers lived, fought bravely and died to defend their homes, is today a peaceful oasis, and a favorite spot to meet with friends and family. It remains, however, a powerful and vigilant bulwark in defense of Puerto Rican identity and culture.
As you leave El Morro today, watch for the stairs at the end of the bridge connecting the fort with the green field. You can take these stairs down into the moat, which, incidentally, was always a dry moat, and see how difficult it would have been to scale the fort’s walls.
You can also walk through the moat toward the ocean side of the fort and find the entrance to a trail that will take you around El Morro, outside and below its walls, back to one of the city’s original gates, la Puerta de San Juan, which would close at night to keep out unwanted visitors.
We hope you’ve loved this audio guide as much as we loved putting it together for you. Remember there’s more content on this same podcast feed: more audio guides are up now, including one for San Cristobal Castle and the Puerto Rico Art Museum and we’re putting new guides up all the time. There’s also Puerto Rico Now, updated weekly, with insider tips to what you might be interested in doing while you’re here visiting. Finally, please remember to leave us a review and subscribe to the show on your podcast app of choice or, if you’d like, to leave your friendly guides a tip at puertorico.freeaudioguides.com.
Until our next adventure together, enjoy your visit to Puerto Rico!