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Black Flags Over Florida: Pirates, Privateers, and Raids on the Spanish Coast
Paperback
Colonial Period (1600-1775)Naval History
Publisher: Independently Published
Published: Jul 4 2026
Pages: 262
Weight: 0.78
Height: 0.55 Width: 6.00 Depth: 9.00
Language: English
Spanish Florida was never safe when a strange sail appeared on the horizon.
For more than two centuries, Florida's coast was a place where empire, violence, storm, and ambition met. Spain claimed the peninsula as a shield for its Caribbean world, but the same geography that made Florida valuable also made it dangerously exposed. St. Augustine stood as a poor but vital foothold, watching waters crossed by treasure fleets, privateers, smugglers, raiders, soldiers, missionaries, and men whose names changed with the flag above them.
Black Flags Over Florida follows the dangerous coast from the struggle between Fort Caroline and St. Augustine to Francis Drake's burning of the town, Robert Searle's buccaneer raid, Carolina attacks on the mission frontier, the building of the Castillo de San Marcos, the wrecks of the 1715 and 1733 treasure fleets, and the legends of Black Caesar and Gasparilla. It also traces the later borderland world of William Augustus Bowles, Gregor MacGregor, Luis Aury, Amelia Island, and the last unstable years of Spanish rule.
This is not a simple tale of buried treasure and pirate romance. It is a story of exposed settlements, contested law, Indigenous homelands, enslaved and free Black lives, imperial rivalry, hurricanes, smuggling, and memory. Before Florida's pirates became legend, they belonged to a real and dangerous coast, where the sea could bring ruin without warning to shore.
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