Pirate Ghosts of the Emerald Coast

Headless Pirates haunt Santa Rosa Sound

by Dale Cox

Santa Rosa Sound at Fort Walton Beach, Florida.

Editor's Note: October is Monster & Mystery Month on Two Egg TV! Check back daily for new stories of monsters, mysteries, and more from Florida, Alabama, and Georgia.

Santa Rosa Sound is a beautiful natural waterway that extends east from Pensacola Bay past Mary Esther and Fort Walton Beach to Choctawhatchee Bay. It separates the sparkling white sand beaches of Santa Rosa Island and the rising condominiums and hotels of Okaloosa Island from the prehistoric Native American mounds and waterfront of Fort Walton Beach.

This stretch of water is a popular playground today, but is it also the haunt of a band of headless pirates? Legend holds that just such a crew is condemned to perpetually sail its surface on moonlit nights. The following report of an encounter with these seafaring specters appeared in Florida and Alabama newspapers in 1921:

One night Mr. Lee Jernigan’s vessel was sailing up the sound, just drifting along. As they passed Pirates’ Cove a yawl came out of the cove and was rowed alongside. Mr. Jernigan was below. There were three men on deck, and they declared that every man in the yawl was headless that they watched the boat several minutes, when all at once—just like a flash—boat and men disappeared. The three men took oath, kissed the Bible, and swore that they saw this. [1]

Santa Rosa Sound on a "ghost story" perfect winter's day.

Pirates' Cove is a shallow body of water within the limits of today's Gulf Islands National Seashore. It is directly across Santa Rosa Sound from the City of Mary Esther, Florida. Entirely surrounded by the dunes of Santa Rosa Island, it is connected to the sound by a shallow inlet. 

The vicinity achieved note in 1906 after a significant storm exposed a cache of lost treasure:

...Spanish coins have been found in the sands of Santa Rosa Island, and only a few years ago, 1906, after a great storm twenty were found on the island in the sand. This find was on Santa Rosa Island, opposite Mary Esther. They were stuck together, showing that they had been buried for a long time aggregated in value several hundred dollars. Not far away is Pirates’ Cove, a little bay in Santa Rosa Island, so named because a pirate ship was sunk there.[2]

The Face of a Real Pirate
William Augustus Bowles as painted
in London in 1790.

The ghosts of the lost pirate and his crew, of course, are said to be searching for their lost cache of coins. They are presumed to also be protecting other treasures that remain hidden on Santa Rosa Island and along the shores of Choctawhatchee Bay. 

Anyone familiar with food and fun on the Emerald Coast is familiar with Fort Walton Beach's legendary Billy Bowlegs Pirate Festival. This fun escapade has been part of the local cultural scene since 1953 and celebrates the "life" and lore of a supposed pirate named Billy Bowlegs. The founders of the festival associated their event with the adventurer and pirate William Augustus Bowles, who prowled the waters of the Gulf of Mexico in 1799-1803. (Note: The real Billy Bowlegs was an important Seminole Indian chief. William Bowles never used the name).

So far as is known, Bowles never sailed from Choctawhatchee Bay, but the best pirate stories are not always the most authentic! The festival is fun and does exactly what its founders intended by bringing tens of thousands of visitors to enjoy a weekend in Fort Walton Beach.

Long before the pirate festival came into being, though, the ghost pirates were a force to be reckoned with for those sailing in Santa Rosa Sound. Strange lights were seen on the island at night in the vicinity of Pirates' Cove, and many fishermen swore to their own encounters with the spirits:

"You may ask any sailor who has passed Pirates’ Cove at night," continued the newspaper accounts, "and he will tell you of the lights and boat and headless men and if he has not seen them his ship mates have."

One man was so frightened by his encounter with the ghosts that local residents swore and began to tremble so badly that "he became bowlegged." 

If you want to see the pirate ghosts for yourself, just enjoy a midnight boat ride west from Fort Walton Beach down Santa Rosa Sound in the direction of the Navarre Bridge. The red pin on the map below points out Pirates' Cove.

Editor's Note: The lands surrounding Pirates' Cove are part of Gulf Islands National Seashore. Treasure digging is strictly prohibited and can lead to a lengthy prison term!