Pulse News Mexico photo/Rich Grant


More than 100 years before the U.S. Civil War, the first underground railroad to freedom for escaped slaves didn’t go from the South to the North – it went the other way, from Georgia and the Carolinas to Florida. And ironically, the escape route often ended in the one place blacks could be free from recapture – Cuba!

Fort Mose was one of the first places in the United States where Blacks were protected from slavery. Pulse News Mexico photo/Rich Grant

That’s because in 1738, more than a quarter century before the so-called “Declaration of Independence” was written in Philadelphia, down in St. Augustine, Florida, they had Fort Mose — a fort and town of run-away former slaves who had been granted freedom by Spain. Amazingly, they had been granted freedom for doing the exact same thing the people in Philadelphia were trying to do in 1776 – fighting the British.

The tale begins in St. Augustine, which in 2015 did something that no other town in the United States has ever done. It celebrated its 450th birthday. But surviving as America’s oldest city hasn’t been easy. St. Augustine has been sacked and burned to the ground. Three times! It has been fought over in so many wars that the Spanish, French, British, Confederate and pirate flags you see flying around town are not just for decoration – they actually represent countries (or criminals) that at one time or another controlled it.

Fort Mose is a place of incredible charm and beauty, as well as a important site for Black history. Pulse News Mexico photo/Rich Grant

One of the least-known stories is that St. Augustine offers a glimpse at Black history that few people know existed. It’s also a great little vacation town. Ironically, after surviving centuries of hurricanes and bloody warfare, this small settlement, originally located in the middle of nowhere on the edge of swamps filled with mosquitos, rattlesnakes and alligators, has grown into one of the most lovely and beautiful cities in the New World.

It is a place of incredible charm with cobblestone pedestrian streets lined with quiet plazas and outdoor cafes shaded by palm trees. There is a European feel, which is highlighted by something very rare in the United States – a great stone citadel that sits squarely in the center of the town.  There are cute little shops and art galleries.  Spanish moss hangs from the trees, while a full-size Spanish galleon brimming with canons floats in the harbor. Of course, being in Florida, it has beautiful beaches, but rare for Florida, there are also dozens and dozens of 100- and 200-year-old buildings that have been repurposed into museums, antique stores, pubs with jazz and live music, and candlelit restaurants.  But don’t forget, this is St. Augustine.  Which means even the oldest buildings can only date back to 1702.  That’s the last time pirates sacked the city and burned it to the ground.

Pirates, Privateers and Privations

In 1565, Spain had a problem. Hernán Cortés had conquered and looted Mexico, filling huge treasure ships with gold and silver bound for Europe. However, for the treasure ships to get to the Gulf Stream that would carry them across the Atlantic, they first had to sail up the treacherous coast of Florida, and as the maps at the time said, “here there be pirates.” Full-blown pirates (outright criminals) and privateers (essentially, pirates who had a letter stating they were fighting for one of Spain’s enemies, like England or France) would wait and capture the slow moving treasure ships, or run them up on reefs and salvage the wreckage.

Fort Mose has been fought over by the Spanish, French, British, Confederate and pirates, and the flags you see flying around town actually represent countries (or criminals) that at one time controlled it. Pulse News Mexico photo/Rich Grant

In 1565, the French went so far as to build a fort in Florida to aid their pirates. Spain had to act. So it sent an expedition of 800 men and women under Don Pedro Menéndez de Aviles to protect and settle the Florida coast. The French were soon dispatched (a nice historical way of saying they were murdered and buried) and, with the coast secure, the Spanish laid out the first European grid-style town in the continental United States.

This was a real city, with streets and plazas and impressive government buildings – and no food. Florida was then a hot, humid, bug- and snake-infested swamp, filled with disease and with little solid ground to grow crops. The early years here were incredibly difficult.

And then there were the pirates. Nine wood forts were built, and destroyed by pirates. The infamous Sir Francis Drake burned the town in 1586, 34 years before the pilgrims landed at Plymouth Rock.

In 1672, Spain had enough of the pirates and began building the Castillo de San Marcos – the oldest and best-preserved stone fort in the continental United States. Pulse News Mexico photo/Rich Grant

Finally, in 1672, Spain had enough and construction started on the Castillo de San Marcos – the oldest and best-preserved stone fort in the continental United States. Today, the huge diamond-shaped fortress is a National Monument. You can walk the ramparts along the top of the towering, 28-foot-tall walls, defend the drawbridge, climb out on the bastions for a view of the harbor, and watch cannons being fired by re-enactors in Spanish uniforms. The fort was built of coquina, a soft local stone made of compressed shells. When the British attacked in 1702, the soft stone absorbed the cannonballs without crumbling, and the fort held out for 50 days. Of course, the frustrated British had to settle for capturing the town, which they burned to the ground before sailing off. But the fort survived that battle and another brutal British bombardment in 1740. It was never captured.

Among the people who built the Castillo were many African Americans. Spain allowed slavery, and there had been African American slaves in the first expedition to Florida in 1565. But slavery in Spain was different from other European countries and had nothing to do with race. Both Blacks and whites could be free or they could be slaves, and if slaves, they could earn their freedom by becoming Catholics and by serving in the military. Children born of freed slaves would be free. Spanish slave codes dated to the 13th century, and when Spain came to the New World, the same laws applied, which were called Siete Partidas. This doctrine held that slavery was against natural law, for God had created man to be free. But to be free, the person had to accept the Catholic Church.

The city’s multiethnic roots are reflected in its picturesque architecture. Pulse News Mexico photo/Rich Grant

This was a completely different system than what the British employed in the 13 colonies to the north, where slavery was eternal. For the mass numbers of enslaved Africans taken to the British colonies (an estimated 12.5 million), not only were they slaves for life, but so were their children and grandchildren and on and on without end.

It’s no wonder that the slaves held captive in the nearby British Carolinas and Georgia would seek the freedom to be found in Spanish Florida. But escape was not easy. Runaway slaves stole horses and boats, or walked through swamps, in a desperate attempt to reach freedom, traveling along this first underground railway, which actually ran from north to south. The first escaped slaves arrived in St. Augustine in 1687. When the British demanded their return, the Spanish Governor Diego de Quiroga refused, establishing a fugitive slave policy for Florida. The newly freed slaves adopted Spanish names and customs, but with an African flair.

By 1738, a community of 100 former slaves were living in an area two miles north of St. Augustine called García Real de Santa Teresa de Mose, or Fort Mose for short (pronounced moe-say). It was the first legally sanctioned Black community in North America, and was an earthen-walled fort with Indian-style thatched huts.

The European history of the town in reflected in its décor today. Pulse News Mexico photo/Rich Grant

The fort was under the leadership of Captain Francisco Menéndez, a remarkable African-born Mandingo and escaped slave, who had already fought the British in Georgia. In 1740, a British naval force attacked and destroyed Fort Mose, forcing the inhabitants to retreat to St. Augustine, which the British then placed under siege.  For weeks, the English bombarded the Spanish fort, but then, in a daring pre-dawn raid, Menéndez and the black militia, along with 300 Spanish soldiers, launched a surprise attack on the British camp that left 68 redcoats dead. The English had enough and retreated to Georgia. Menéndez was a hero … to the Spanish. To the British? Well, of course, they considered him a pirate!

A year later, in July 1741, Menéndez was sailing on a Spanish ship to Havana to be rewarded for his bravery when the ship was captured by the British. At first, the British wanted to castrate him and he was tied to a gun to await punishment, but many of the white Spanish crew members came to his defense. In the end, the British gave him 200 lashes and “pickled” him, that is, they ran salt and vinegar onto his back to increase the pain. He was brought to the Bahamas, and sold as a slave.

When Florida was ceded to the English, slavery was restored for the inhabitants of Fort Mose. Pulse News Mexico photo/Rich Grant

No one knows exactly what happened to him for the next 11 years, but he obviously escaped and showed up again back in St. Augustine in 1752, where he rebuilt Fort Mose. A second Black community was established here and thrived until 1763, when, in a treaty approved to settle European wars, Florida was ceded from the Spanish to the English. This meant a return to slavery for the inhabitants of Fort Mose, so instead (in one of the great ironies of history), they fled to Cuba, where they could still be free.

Fort Mose was abandoned and slowly faded back into the swamp. In 1821, Florida became a territory of the United States, and a slave state. A public slave market was built in the center of St. Augustine in 1824, where slaves could be sold. This became a focal point of demonstrations during the Civil Rights movement in the 1960s. In 1964, the marsh where Fort Mose had stood was declared a National Historic Landmark, and today there is a wonderful museum there telling the story of the fort and the free people who lived in it.

In 1964, the marsh where Fort Mose had stood was declared a National Historic Landmark. Pulse News Mexico photo/Rich Grant

After you’ve toured Fort Mose, head two miles into town to see the incredibly large Castillo with its 60 cannon that was built to fight pirates. Then it’s time to leave the fortress, cross the moat and then cross the street to continue the story from the other point of view at the St. Augustine Pirate & Treasure Museum.

This is the largest and most authentic collection of pirate artifacts ever displayed under one roof. Of course, there are not a lot pirate artifacts. Most of the pirates were hung or killed in battle (Blackbeard went down with five bullet holes and 20 sword cuts, and then they sliced off his head for good measure).

So there’s not a lot of genuine artifacts, but you can see Blackbeard’s blunderbuss, one of the three remaining “Jolly Roger” pirate flags, the world’s oldest wanted poster and Captain Thomas Tew’s original treasure chest – the only known authentic pirate chest in existence. The museum does a fun job of detailing the lives of the most outrageous of the scallywags, and kids can fire a cannon, see a Disney-produced special-effects show on Blackbeard’s last battle, and stare at the actual sword used by Captain Jack Sparrow in the movie Pirates of the Caribbean. The sword spins in a special case with dramatic lighting as if it were a priceless relic, and maybe it is.

Most interesting are the exhibits of real treasure, including pieces of gold, gold bars, pearls and silver, recovered from pirate shipwrecks. Pulse News Mexico photo/Rich Grant

Most interesting are the exhibits of real treasure, including pieces of gold, gold bars, pearls and silver, recovered from pirate shipwrecks, including Blackbeard’s own flagship, the “Queen Anne’s Revenge.”  Pirates had no color barrier, and Blacks and whites served equally side-by-side on pirate ships, sharing in the booty, and in the punishments. One of Blackbeard’s chief lieutenants was Black Caesar, a gigantic African chief who was enslaved and later became a pirate. He was captured during Blackbeard’s last battle and hung in Williamsburg, Virginia.

This museum is just one of a half dozen pirate adventures in St. Augustine. This is deep pirate country, and if you doubt it, there are not one, but two stores that sell nothing but pirate costumes, from tri-corner hats to boots, swords and pistols. Up to a dozen fully outfitted pirates stroll around town posing for pictures, and there are pirate shows, a pirate sailing tour of the harbor on the Black Raven, and pirate, ghost and graveyard walking tours.

All of which seems quite natural. St. George Street, the cobblestone, car-free main road of St. Augustine, looks like the setting of every pirate movie, with colonial buildings, pubs with wood signs, swaying palm trees, balconies and rustic old lanterns. Yes, it’s a bit touristy, but much of it is authentic, and it’s certainly beautiful at night, with the lanterns glowing and candles flickering in many of the windows.

St. Augustine is also the North American port of El Galeón, a replica of a typical Spanish galleon. Pulse News Mexico photo/Rich Grant

St. Augustine is also the North American port of El Galeón, a replica of a typical Spanish galleon. The 170-foot-long, 495-ton El Galeón sails from New York to Puerto Rico, telling the stories of these heavily armed cargo ships that were like full cities under sail. The ship is frequently in dock in its main port, St. Augustine. The El Galeón is similar to the San Pelayo, the flagship that first carried Menéndez to Florida in 1565. That ship carried 77 crew, 18 gunners, 317 soldiers and 26 families, as well as provisions, including cattle.

Among the crew were several African American sailors, who came to America as slaves, but died as free men in the New World.

If you go, be sure to check out the city’s website.


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