Pirates & Pineapples – History of Elliott Key

Located entirely within Biscayne National Park, Elliott Key has an intriguing history of pirate lore and pineapple pioneers. The stories range from pure legend to historical fact, with many lines blurring in between. 

Elliott Key is the largest island in the park at about 7 miles long and 2,500 feet at its widest point. It was previously named Ledbury Key, getting the name the same way many Keys islands do: from a shipwreck. 

The two-masted square-rigged sailing ship, known as a snow, ran aground in 1769. Three years later, cartographer William de Brahm described the shipwreck in his 1772 Atlantic Pilot: “The vessel bilged in shallow water, but an anchor was thrown out, and the next day the vessel was found to have grounded on Elliott’s Kay, with its anchor among the trees.”

Elliott Key is now an uninhabited retreat for campers, hikers, and fishermen, but it was once home to Native Americans, Bahamian pioneers, and the “greatest pirate that never lived.” 

For millennia, the Tequesta Indians used the island on a transient basis. In more recent history, it was inhabited by Bahamian transplants that turned the island into a planting community. 

After moving from the Bahamas to Key West, Asa Sweeting and his two sons sailed north, looking for suitable farmland and finding it on Elliot Key. In 1882, the family claimed just over 154 acres under the Homestead Act of 1862 and later purchased an additional 85 acres.

The Sweetings quickly developed 30 acres of farmland, producing pineapples, tomatoes, and key limes. They constructed multiple houses and buildings as their family and farm expanded, including a storm shelter at the center of the island.

The storm shelter proved useful in 1906 when a Category 3 hurricane hit and left the island’s inhabitants marooned for 3 days. Though the family survived, their crops were destroyed, and worse, the now salt-laden earth became infertile for pineapple farming. 

Though key lime trees continued to flourish, they were not enough to sustain the Sweeting family. Within two decades, all of the Sweetings abandoned the island. 

Around that time, a man named Charles M. Brookfield purchased 20 acres on Elliott Key and built a fishing lodge. Brookfield was a historian, treasure hunter, and writer who was perhaps seeking the infamous Black Ceasar Treasure.

Many legends of Elliott Key claim it was once a refuge for escaped slaves and pirates. The most famous legend of the island involves a slave-turned-pirate called Black Ceasar. Though there are several varying accounts of Black Ceasar’s origins and his escapades, most versions of the tale describe him as a huge man with immense strength. 

Though details differ, the overriding story is of a black man who escaped enslavement and gained riches through piracy. Elliott Key and the surrounding islands are believed to have been his base, with millions of dollars worth of his treasure buried in its sands. Unfortunately, little evidence of such treasure, or even Black Ceasar himself, has been uncovered.


The stretch of land that was once worked hard for farming and purportedly used as a refuge is now snuggled in a marine national park. Biscayne National Park protects waters, islands, and reefs and has become a top destination for boating, fishing, and diving. 

Elliot Key is uninhabited but is open to campers on a first-come-first-serve basis. The island is only accessible by boat, and its 7-mile “Spite Highway” trail is the longest hiking trail in the park. Understandably, the term “hiking” is used loosely in this marine national park.

The hiking may not be rigorous, but who knows, you might stumble upon buried pirate treasure! Or, at the very least, you can find a comfy spot to relax where groves of pineapples once grew.

*References: upperkeys1.com/elliot-key/; nps.gov/bisc; nps.gov/parkhistory; floridarambler.com/historic-florida-getaways/pirate-black-caesar-florida-keys/
*Photo Credit: Florida Keys History & Discovery Center

–Jerrica Mah is a writer, Army wife, and freelance book editor, who loves to travel with her family.

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