The Great Pirate Towns of the Americas

One of the guns at old Fort Charlotte in Barbados, which now guards the swimming pool at the Hilton Barbados Resort and is the perfect place for sunsets.

Ever since there have been boats, there have been pirates. What could be easier for criminals than robbing a ship on the high seas, far from prying eyes and any type of protection? Especially when the ships at sea could be carrying treasures of gold and silver.

One of the world’s few original pirate flags, St. Augustine Pirate Museum

It’s no wonder that desperate men turned to piracy to seek their fortune.  Although most of them were hunted down, killed in battle, or hanged, they left behind a swashbuckling legacy that can still be experienced in a variety of forts, historic harbors, and museums. So, sign aboard matey, and let’s set sail to the great pirate towns of the Americas.

The guns at old Fort Charlotte in Barbados, which now guards the swimming pool at the Hilton Barbados Resort.

The Buccaneers and Brethren of the Coast

The walls of Cartagena are studded and cannons, many of which have been turned into bars and restaurants

When Spain conquered Central and South America in the 1500s-1600s, they had one problem: how to get the stolen treasures back home? They decided to assemble huge fleets at the largest port on the Atlantic, Cartagena, Columbia. Here, under the protection of a fortress, Spanish soldiers could bring the gold, silver, and emeralds they plundered and stow them on heavily armed warships for the final dash to Europe. Of course, also waiting in ships just offshore were pirates.

The romantic streets of Cartagena are lit by historic lanterns

One of them was the famous privateer, Sir Frances Drake. In 1586, he attacked and sacked Cartagena. Incredibly, the Cartagena headquarters used by the pirate El Draque is still there. With its massive iron doors and stone walls, it is a wonderful place to begin a tour of stunningly beautiful Old Town Cartagena. The UNESCO World Heritage City is surrounded by 11 km of walls, making it the largest walled city in South America. While the ramparts are brimming with cannons and towers, inside the walls, the town is filled with pleasant cobblestone streets lined with shops, hotels, and homes painted a rainbow of pastel colors. Two dozen horse-drawn carriages clatter around at night, and with old lanterns glowing under palm trees, it’s a romantic dream of a pirate haven.

You can learn about the real pirates who attacked Cartagena at the Naval Museum (exhibits in Spanish only, but English guides available) or at the massive San Felipe de Barajas Castle, the largest single fort in the Americas, built on a hill above the town.  Why build a fortress on a hill instead of in the harbor? Because that’s how Drake attacked and sacked the city.

San Felipe de Barajas Castle, the largest fortress in South America

Protecting the Caribbean

El Morro, the Bull, is the Castillo San Felipe del Morro, and one of the best interpreted fortresses in English in the world since it is now a National Park

Once the treasure fleets left Cartagena, they had to sail the treacherous waters of the Caribbean. To protect them, Spain built two incredible fortresses, El Morro – “the Bull” and Castillo San Cristobal, at the entrance to the Caribbean in San Juan, Puerto Rico. Now maintained by the National Park Service, their towering stone walls and museums present the most in-depth look at the lengths the Spanish had to go to fight these pirates. Did the defenses work? Well, our friend pirate Drake attacked San Juan in 1595 – and failed to capture the town.

National Park ranger in El Morro fortress

Today, the forts overlook the peninsula of Old San Juan that juts into the Caribbean like a thumb. Here, the sea is sparkling blue, beaches begin at the edge of the fortified stone walls, and the harbor, once filled with galleons, is now packed with a fleet of the world’s largest cruise ships. Nearly every house is covered with flowering trees, and (fittingly for a pirate town) you can tour the world’s largest rum distillery – Bacardi’s.  Even the historic streets (Adoquines) are colorful. They are made of blue bricks that were cast from furnace slag and brought over on Spanish ships as ballast. Under the light of flickering lanterns, the streets glow with color as deep blue as the sea.

Walls surround the historic shore of Old San Juan, Puerto Rico

Catching the Trade Winds

Castillo de San Marcos was built of coquina, a local soft stone that absorbed cannonballs and was able to withstand a British siege {“DeviceAngle”:-0.337625}

Next, the Spanish treasure fleets had to sail to the eastern shore of Florida to catch the favorable trade winds to Spain. It was here that they were most vulnerable to pirates, so in 1565, the oldest city in the United States, St. Augustine, FL, was built for one purpose: to fight pirates. The Spanish came to the hot, humid, bug-infested swamp that was Florida and laid out the first European grid-style town, a real city with streets and plazas. For protection, nine wood forts were built — and destroyed by pirates in just the early years. Our friend, the infamous pirate Drake, burned the town in 1586, 34 years before the Pilgrims landed at Plymouth Rock.

Entrance to the Castillo de San Marcos

By 1672, Spain had enough and construction started on the Castillo de San Marcos – the oldest and best-preserved stone fort in the United States. Today, the huge diamond-shaped fortress is a National Monument. You can walk the ramparts along the top of its 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.

Pirate Treasure Museum

It’s just a musket shot from the fort to 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 many pirate artifacts! Most of the pirates were hanged or killed (Blackbeard went down with five bullet holes and 20 sword cuts, and they sliced off his head for good measure).

St. Augustine, Florida has been burned by pirates and the British, but is now a beautiful colonial town of plazas and fountains

So, there are not a lot of genuine artifacts, but you can see Blackbeard’s blunderbuss, one of the three remaining “Jolly Roger” pirate flags, and Captain Thomas Tew’s original treasure chest – the only known authentic pirate chest in existence.

St. Augustine captures feel of a pirate town

The museum is just one of St. Augustine’s pirate attractions. On their quaint pedestrian streets lined with taverns and shops, you can’t throw a cutlass without hitting some mention of pirates.  Or even a real pirate. A half dozen people in pirate costumes continually walk the streets posing for pictures.

St. George Street looks like a setting for pirate movies

The Richest Place on Earth

The view of Bridgetown, the capital of Barbados, from the Hilton Barbados Resort

England missed out on the gold and silver of the New World, but they found another treasure.  Sugar. Britain introduced coffee in 1650, chocolate in 1657, and tea in 1660. Sugar consumption quadrupled and then doubled again. It was white gold. And then some genius discovered how to make rum out of a worthless sugar byproduct, molasses. By the late 1600s, Barbados, a little coral island off the coast of Venezuela, was found to be perfect for growing sugar and it quickly became the richest place on earth with a population of 75,000 – larger than all 13 American colonies combined. Of course, most of the population were enslaved Africans. To oversee the enslaved and fight off pirates, Barbados had to be defended. Unlike the Spanish, who built one huge fortress to protect a port, Barbados constructed 42 different forts armed with 463 cannons.  Pirates never attacked it. But its rich merchant ships stuffed with sugar, slaves, and rum became the pirate’s favorite target.

The Sentries & Corps of Drums of Barbados holds a changing of the guard ceremony on Thursday mornings

Today in Barbados, you can tour The Garrison which was the center of British defense in the Western Hemisphere for 100 years. A UNESCO World Heritage Site, it is the most authentic military garrison in the British empire with cannons, tunnels, and a fun weekly changing of the guard.  Rum was invented in Barbados and if you want to drink like a pirate, there’s no better place than on tours at Mount Gay, the oldest distillery in the world.

The Pirate Republic

Nassau maintains its colonial tropical feel and the nation’s official seal, still displayed on government buildings, is Expulsis Piratis — Restituta Commercia — Pirates Expelled, Commerce Restored

One reason Barbados was not attacked was that during the “Golden Age of Piracy” (1650-1725), the greatest conglomeration of pirates in history assembled at Nassau, the Bahamas, where the corsairs created their own country — an actual Pirate Republic that terrorized the Americas and even challenged the European powers. All the famous pirates made it to Nassau – 2,000 outlaws including Blackbeard, “Calico Jack” Rackham, the women pirates Anne Bonney and Mary Read, and Captain “Black Bart” Roberts, who said of pirating, “It was a short life and a merry one.”

Woodes Rodgers statue in the parking lot of the British Colonial Hilton Hotel, Nassau. He looks better here than he must have in real life. When he was a pirate, he got shot in the face, blowing away his jaw and many of his teeth

Today, Nassau is the pirate capital of the Americas. The Pirates of Nassau Museum is a hoot – a bit like walking (instead of floating) through Disney’s Pirates of the Caribbean ride with a reproduction of Blackbeard’s ship, the 130-foot-long, 16-gun corvette, The Revenge. The ship creaks, seagulls squawk, and water laps at the stone quay. How good the illusion is may depend on how many beers you had at the nearby Pirate Republic Brewing Company. But kids are sure to enjoy it and the museum does a fantastic job of telling the true historical story of the rouges who once ruled this town. Eventually, England tired of the pirate nuisance and sent Woodes Rodgers (a former pirate himself) to Nassau in 1718 with three warships and an ultimatum for the pirates to choose: “Death or pardon.”  In short order, Rodgers cleaned up the pirate den. He described his actions as Expulsis Piratis – Restituta Commercia, words that still adorn the official seal of the Bahamas – “Pirates Expelled – Commerce Restored.”

A life-size replica of Blackbeard’s ship
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