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Okaloosa County has a rich history spanning many centuries and four Countries; it is no wonder that Okaloosa Island, Fort Walton, Destin, and Mary Esther abound with ghost stories

a group of people rowing a boat in a body of water

Santa Rosa Sound, directly across from Mary Esther, is home to one of the most haunted sites, Pirates Cove. The cove is rumored to have been used as a pirate base, the perfect place to hide bounty stolen from merchant ships. Others believe it was only used as shelter during bad storms.  

Pirates Cove is a historical treasure and an important, beautiful ecological system. The cove is only accessible by water as it is owned by the Air Force base, and trespassing on the land, including the 50-foot-tall dunes, is prohibited.  However, this type of protection provides the perfect rookery for many ground and tree-nesting birds and a fish hatchery for the local fish species.  Making major contributions to the health of the ecosystem.  

This area’s rich history includes buried treasure from pirate attacks, a headless maiden in white forever walking the sands, and centuries-old headless oarsman’s hauntings.

The Lady’s Walk

The Ghostly Apparitions, called the Lady’s Walk, dates back 207 years and is rooted in events of 1816 or 1817. There are multiple legends about what happened to the young maiden in white and why she is forever tied to walk this haunting, beautiful place. The two haunting tales handed down over time include the capture of the Spanish Galeon with a Princess on board or a Spanish maiden living on the Island but mistakenly killed by her lover. 

a sunset over a body of water

The Spanish Galeon Legend

This area was still under Spanish control and had not yet been turned over to the United States. So, the legend and facts line up with the type of ships that would have been using these waterways in the early 1800s. The Golden Age of Piracy peaked in 1720 when thousands of pirate ships were active worldwide.  The golden age came to an end in the early 1800s.  The unnamed hurricane of 1917 unearthed Spanish gold coins supporting the buried treasure rumors. Again, the timeframe of a Lady Walking matches history. 

Any ship approaching your vessel with the “Jolly Roger” skull and crossbones flag struck terror for all aboard. Imagine being a young Princess on a Spanish Galeon and seeing this flag on an advancing boat.  

The Mistaken Embrace 

The second legend states that a seaman fell madly in love with a Spanish madien who lived on the Island.   The young couple made plans to flee. Her father found out and locked her away, for he had committed her to marry a rich old don with high standings.  Her lover walked the shoreline for weeks, waiting for his love to join him.  One night, she escaped and ran to their meeting place, where her father’s suitor accosted her.  The young man was on the shore waiting for her when he saw what he thought was an embrace instead of a struggle. She was frantically trying to reach him, not willingly accepting the embrace of another man. He was so enraged he drew his sword and killed them both. 

Which story do you think rings true? 

The timelines for the second story does not match as closely to the history of this area; the last Spanish settlement on the island was in 1762. If the story timeline is correct, around 1816, then we are 54 years late.  However, this is the story most often shared by the second generation of settlers to Mary Esther.

a body of water

Right of Passage

Visiting this area at night is a right of passage.  Most long-term local residents started venturing to Pirates Cove at ten years of age. Recently, a local committeeman shared that he saw something on a full moon many years ago.  To this day, he can’t say what he saw but insists that there were drag marks in the sand the next day, which could have been left by a long gown and someone pacing. 

Four Headless Oarsmen: Another haunting tale centers around a small boat called a Pinnace; it is a low, flat vessel propelled by oars and used to move items from a larger ship to shore.  There are reports dating back a hundred years of a Pinnace floating aimlessly through the water or moving in sporadic bursts, which is uncommon for well-trained sailors.   Each report has a faint glow of light as if from an old oil lamp.  People are drawn in closer and closer to see if the boaters need help.  However, their curiosity soon turns to terror when all four men turn in unison, and you realize they are headless. The reports include testimonials from respected citizens during the early 20’s.    After the encounter, one man never went on the water again; one turned bowlegged due to his legs knocking together, and the third moved and never spoke about the incident.

a body of water with a city in the dark

Hauntings? Imagination? You decide!

Our night-time Glow Tours is the perfect way to experience Pirates Cove at night.  This tour is not for the faint of heart as we adventure in the dark with the glow lights from our clear kayaks leading the way.  We can’t guarantee a ghostly encounter, but we can guarantee a unique glowing experience! Book today!