Heaven, you fool? Did you ever year of any pirates going thither? Give me hell, it’s a merrier place.

Thomas Sutton

I have an obsession with pirates. I read books about them, my alma mater’s mascot was a pirate, that same college helped excavate Blackbeard’s ship, and I’m just fascinated by them. While I fully understand they lived ruthless lives, pirates have always kept me fascinated, at least the historical ones have, not the modern ones.

After having spent almost an entire year without a significant adventure, I needed to feel the wind in my sails, so pirates are my theme this week and I’m super excited to write this. We all know about some of the most famous pirate strongholds throughout history, but some of the following may surprise you. Once the travel restrictions are lifted, think about adding a swashbuckling destination to your list.

Port Royal

Location: Jamaica

Hist-arrrrr-y: The golden age of piracy (late 17th-early 18th centuries) made Port Royal a household name where pirates and smugglers were concerned. While the town had been hit by piracy as early as the 1600s, Jamaica’s governors offered Port Royal as a safe haven to pirates on the condition they protect the island from the Spanish.

Pirates used the town as a base where they could plunder Spanish ships and towns and then spend their winnings gambling, drinking and on prostitutes. Nicknamed the ‘wickedest town on earth’ Port Royal prospered, albeit in a less-than-reputable manner. Once pirates started attacking many ships in the area, not just the Spanish, Port Royal’s governors took action against these plundering seafarers. Gallows Point was established ~1720 where several notable pirates were hanged.

Today you can scuba dive with the part of the city that sits underwater, giving you an eerie step back in time. There is also an archaeological museum that will teach you the town’s full history.

St. Mary’s Island

Location: Madagascar

Hist-arrrrr-y: Most successful pirates were active in the Indian Ocean near some of the richest empires of the time. Madagascar had only one, but several pirate strongholds from which they operated their swashbuckling on European and Asian merchant ships. St. Mary’s was the most frequented location for pirates venturing to Madagascar and they used the island to restock their supplies before heading back out to sea.

Today, barely anything remains of the piracy and infamous pirates who traveled to the island. However, the only pirate cemetery in existence is located there and offers an extremely interesting, albeit morbid, attraction.

Tortuga

Location: Caribbean

Hist-arrrrr-y: In the 1600s, this island was the stronghold for pirates who (fun fact) were the originators of the term buccaneer. These pirates were mostly French pirates who preyed on Spanish ships in the area. After the pirates (originally adventurers, thieves, and escaped slaves) fled Hispaniola they decided to fortify Tortuga. In 1630, Jean le Vasseur helped engineer the 24-gun castle, Fort du Rocher.

As more and more pirates arrived, many formed the ‘Brethren of the Coast’ and established their own laws. They were particularly savage against the Spanish in the area which led to repeated attacks on Tortuga itself. Pirates here also seemed to be particularly combative amongst themselves. The violence got so bad at one point that the French governor brought 1,650 prostitutes to distract them. Sadly, there’s no evidence whether this unique solution was successful or not. By the 18th century, most pirates had left the stronghold.

Today there are several places you can visit. Several caves are open to tourists that were used for smuggling and several historical buildings still exist, including the fort.

Clew Bay

Location: Ireland

Hist-arrrrr-y: There’s nothing quite like a strong woman defying all expectations, especially during the 1500s. During a time when Ireland was controlled by chieftains, Grace O’Malley emerged as one of the most formidable lady pirates. Under her leadership, her clan controlled and plundered much of the coast with the 20 ships and hundreds of men under her control. These pirates set up their base at Rockfleet Castle and defended their territory against both government officials and other pirates.

After being jailed for months, soon after her release she was back to swashbuckling. Not only was she a leader but she was well-versed in fighting and politics. She even successfully negotiated with Queen Elizabeth I for the return of her ships and her son’s release from prison.

Want to go visit the home base of this famous pirate and see the coast her crew defended and plundered? Not much remains of Rockfleet Castle, but there is one structure still standing and very much open to visitors.

New Providence

Location: Bahamas

Hist-arrrrr-y: Nestled perfectly along trading routes, New Providence was the ideal location for pirates to find safe harbor, resupply, and make repairs. Many of the most famous pirates, including Blackbeard, made stops here frequently. Unfortunately for the pirates, the reputation of New Providence became so worrying that several British war ships were dispatched to regain control of the area. Pirates who surrendered were offered pardons, but those that resisted were hunted down.

What was once a pirate stronghold, turned into a base for anti-piracy operations in the Caribbean. Today, pirate-related attractions are limited to museums, forts constructed by the British to protect the island, pirate ship tours, and the stretches of beach where pirates would come ashore.

Barataria Bay

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Location: Louisiana

Hist-arrrrr-y: In the early 19th century, pirate Jean Lafitte established himself by attacking ships in the Gulf of Mexico. They earned their notoriety by attacking Spanish ships and smuggling the goods and slaves into New Orleans. Barataria Bay started as a small smuggler’s town and evolved into one of the busiest black market ports in North America.

At any given moment, 12 pirate ships could be found in the harbor and over 500-1,000 pirates were known to frequent the area. Lafitte temporarily stopped his pirating ways during the War of 1812 where he sided with the United States in exchange for a pardon for his past lawlessness. Piracy, it seemed, had a special hold on Lafitte as he later returned to plundering and even established another pirate haven on Galveston Island.

Today, nothing exists of the actual haven, but you can tour the landscape by boat to get a sense of its past and how it served piracy so well.