Boone's tale of the pirate and privateer raids that repeatedly burned and sacked St. Augustine — Sir Francis Drake in 1586 and the pirate Robert Searles in 1668.
You're walking this sweet peaceful street, friend — so let me ruin it for you a minute, and tell you about the days it ran with fire and blood. Ranger Merrick again. Because for its first century or so, this little Spanish town was just about the unluckiest place on the whole coast, and the reason was two words that put ice in a Spaniard's spine: English raiders.
Start with the most famous sea-dog of them all — Sir Francis Drake. To the English, a hero and an admiral. To the Spanish, the devil himself, a pirate with a queen's blessing. In fifteen eighty-six, Drake came sailing up this coast fresh from robbing Spanish towns in the Caribbean, and he spotted the little watchtower here. He landed a small army, and the outnumbered Spanish took one look and fled inland with what they could carry. Drake's men looted the town clean, took everything of value, and then burned St. Augustine to the ground — every house, the church, the fort of the day, all of it, ash. The city was barely twenty years old, and it had already been wiped off the map once.
They rebuilt. Of course they did — that's the whole story of this town, they always rebuild. But then came sixteen sixty-eight, and a genuine pirate this time, an Englishman named Robert Searles. Searles slipped into the bay at night, quiet as a cat, some say flying false Spanish colors to fool the harbor watch. And his pirates fell on the sleeping town in the dark. They sacked it, they plundered it, and they killed some sixty townsfolk in their homes before the night was through. Men, women — it didn't matter to Searles.
And it was that horror — that night of the pirate in the dark — that finally lit a fire under the Spanish crown. Enough, they said. No more wooden forts that burn, no more towns left naked to any cutthroat with a ship. And within a few years, they began building the great coquina Castillo you just laid your hand on — the fort that would never fall — precisely so that a Drake, or a Searles, could never do this to St. Augustine again.
So walk on, friend — but walk on knowing. Keep heading south down Saint George Street; there's plenty more of this old lane ahead.
Photo: Jodocus Hondius I · Public domain
