Tales of the Caribbean Sea, Part I
- Jim Watson
- Oct 24
- 6 min read
Updated: Oct 25

An afternoon thunderstorm, no doubt a spin-off from Hurricane Melissa currently threatening the island of Jamaica, rolls across the city of San Juan, Puerto Rico. Here in the barrio of Santurce where I have my rental unit, life comes to a standstill due to the ensuing deluge. Shop owners linger in their doorways, construction workers lounge under convenient overhangs and laundry set out to dry is hurriedly taken in.
I’m here for the next five weeks in that region of the Caribbean known as the Greater Antilles archipelago to search for storytales, folklore, legends and anything else I deem bizarre, unexplainable or simply interesting. It's all part of my research for the upcoming books Mysterious Island: Puerto Rico and Mysterious Island: Virgin Islands, both coming next year.
But the pleasant family neighborhood of Santurce isn’t where the action is in that regard. For that, one needs to head over to Viejo San Juan, the Old San Juan.
THE GHOSTS OF OLD SAN JUAN
Old San Juan, the original settlement of Puerto Rico’s largest city, straddles the Island of San Juan in the western reaches of the city and has since its founding in 1521. A lot happened in the Caribbean in the decades following Christopher Columbus' first voyage to the New World in 1492 and by that year the Spanish Crown had spread its tentacles across the scattered islands inhabited by the Arawak-speaking Taino peoples and their brethren. The founding of San Juan was one of those things.
As a legacy of this founding, a trio of iron and stone fortresses still stand over the old city like silent sentinels, guarding a violent history and five centuries of deeds and misdeeds. Chief among these fortalezas is the Castillo San Felipe del Morro.
Constructed between the 16th and 18th centuries to guard San Juan Bay, it is part of the UNESCO-listed San Juan National Historic Site and is administered by the U.S. National Park Service. Its massive walls, strategic cannons, and iconic lighthouse withstood attacks from English and Dutch forces, among others. Designed for defense against pirates and invaders, it features six levels of batteries and tunnels.

More than a million visitors come to see the Castillo San Felipe each year, but more than ten times that amount visit a very well-known replica of this same fortress and most don’t even realize it. In Disney’s popular Pirates of the Caribbean ride, the fortress we see that’s under siege from a square-rigged pirate ship is supposed to be Castillo San Felipe and the village that the pirates plunder throughout the rest of the ride represents Old San Juan. Bet you didn’t know that.
Unlike the version in the ride, however, the real Castillo San Felipe was no pushover. The fortress was a formidable obstacle to anyone who had ideas about sacking San Juan and many were the souls who tried and failed.

There were some successes. Sir Francis Drake (who was at the center of a wonderful buried-treasure story on Catalina Island) briefly held both the fort and the town itself before being forced to retreat in the face of Spanish reinforcements and illness among his crew. A ferocious Dutch attempt to take the city also had a limited amount of success and resulted in the deaths of untold hundreds of Spanish and Dutch troops.
Naturally, all that gory glory can’t help but leave a legacy of dark folklore and legends.
THE GHOST PART
Normally I’m not one to go on guided tours, but sometimes such things are the best way to learn the local folklore and legends of a place. I chose San Juan Ghost Tours for a one-hour jaunt mostly through the western portion of the island.
The mysteries started literally under our feet in the underground parking garage when our guide, Mylene, told us that pottery shards and ritual artifacts had been discovered there during the construction, indicating the presence of a significant Taino Native American site. People passing through the parking structure, said Mylene, tell of hearing voices whispering when no one else is around. The few words they can make out are unknown to them and, according to Mylene, when people have looked the words up online they turn out to be words from the Taino language, a tongue that only a handful of Taino speak today.
But Taino isn’t the only language whispered in the dark to unsuspecting tourists and residents. In 1555, a group of French pirates managed to sneak under the guns of the fortress, probably owing to their use of small, swift corsairs rather than lumbering brigantines or carracks.
The French looted homes, churches, and warehouses, stealing gold, silver, and sundry supplies. They set fire to much of the city, including Governor Juan de Guevara’s residence, destroying about two-thirds of the structures in the town. Around 200 Spanish defenders were killed or captured.
But fate took a humiliating turn for the French rogues after their ships ran aground while trying to flee San Juan Bay for the open sea with all their loot. It all went downhill from there and many of de Sores' men were killed and their ships sank with all their treasure aboard. Visitors to the city’s last remaining gate, the Puerta de San Juan, will occasionally report the sound of voices whispering and speaking in French when no one is there. “The French pirates are still trying to get their gold from their sunken ships,” said Mylene.

Nor are these experiences limited to auditory ones. According to Mylene, the devastating attack by Dutch troops in 1625 has resulted in the occasional modern-day visitor mysteriously being overcome by the smell of burning flesh. Additionally, more than one nighttime visitor to the park has seen the translucent forms of Spanish sentries pacing on the upper decks of the fort.
Yet another ghostly tale revolves around none other than Ponce de Leon, the Spanish explorer, conquistador and three-time governor of Puerto Rico. Best known for his lifelong pursuit of the fabled Fountain of Youth, de Leon lived with his family in a house in Old San Juan known as the Casa Blanca.

De Leon met his end while leading a shore party of Spanish soldiers at what was probably today’s Caloosahatchee River in Florida, when his party was attacked by the local Native Americans. For his part, de Leon was wounded in the thigh, a wound which festered until he died in Havana a number of days later.
Within days of his death, his family members and others living in the Casa Blanca began to hear the unmistakable sound of heavy boots pacing on an upstairs balcony, something that the living de Leon did as a matter of habit. The paranormal activity eventually became so distressing to the residents of the house that they all eventually moved to different quarters. The house was abandoned and left to deteriorate until it was essentially gone. In time, a new Casa Blanca was built to replace the old one, a structure that still stands to this day on Calle San Sebastian.
NEXT WEEK: For the Halloween instalment, we’ll break from Tales of the Caribbean Sea and enjoy some ghostly experiences on Catalina Island as related by some of our island locals, including Yours Truly.
NEXT CARIBBEAN POST: On November 7, we’ll return to our multi-part Caribbean adventures, including:
· Ghostly screams from the forest
· The Dreadful Secret of Coffin Island
· The REAL Fountain of Youth?
· And more!








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