Pirate lore is replete with shipwrecks, buried treasure, and infamous villains who, despite formidable mischief, have been romanticized with the passing of stories and time. Such colorful characters and their accompanying exploits are responsible for writing a significant chapter in Caribbean history, including the golden age of piracy between 1690 and 1730.

Today’s adventurer or history buff will be pleased to discover that some of Tradewind Aviation’s most-visited Caribbean islands once teemed with every iteration of buccaneer, privateer, and swashbuckler. Steeped in legend and beautiful as they are fascinating, here are our favorite Leeward Islands destinations to feed the imagination and invoke your inner pirate.

Puerto Rico

Pirate ship in the Caribbean

Ensconced along Puerto Rico’s northeast coastline is the original heart of San Juan. Practically an island of its own, Old San Juan is connected to the rest of the city and the larger Puerto Rican landmass through bridges on its eastern side. Considering its status as the second oldest city in the Western Hemisphere, as well as one of the key ports to the New World, the storied citadel has experienced its share of seafaring scoundrels throughout history.

In the decades after Columbus’s landing, Puerto Rico began to boom as a vital Spanish colony, and competing European powers soon took notice. After a series of attacks from government-commissioned pirates — otherwise known as privateers — began on the port, the Spanish built a wall around the city complete with a series of cannon-studded forts to protect its harbor from seaborn enemies.

Today, the towering rock walls of Fort San Felipe del Morro still overlook the entrance to San Juan Bay, and visitors can tour the UNESCO World Heritage site’s six levels and tunneling mazes while imagining an onslaught of French, Dutch, and English invaders. Further east down the coast of Old San Juan, the sprawling Fort San Cristóbal also remains open for modern day exploration. Completed in 1783 to protect the city from the other direction, it’s known as the largest Spanish fortification built in the New World.

Fort San Felipe del Morro in Old San Juan, Puerto Rico

Take a drive from San Juan to Rincón Beach on the northwest shore of the island to pay a visit to Villa Cofresí Hotel and Restaurant — named after Roberto Cofresí, a legendary local pirate who allegedly split his loot with the island’s poor. Here, guests can sip a Pirate’s Special cocktail from a coconut-shell goblet before inspecting the beach’s cliffside caverns where Cofresí was rumored to have hidden some of his booty.

For a dose of corsair history away from Puerto Rico’s Spanish strongholds, head east to the nearby islands of Vieques and Culebras, which remained lawless outposts for pirates and other pariah for more than three centuries. Naturally abundant in crabs, fish, birds, and timber, these outlying islands provided ideal havens for ships to resupply. In a culmination of rolling hills and verdant forest rising almost 1,000 feet from the sea, the highest point of Vieques is named Monte Pirata, or “Pirate’s Mount,” from which freebooting inhabitants once glassed the surrounding blue vistas.

British Virgin Islands


A chain of more than 60 islands thoroughly riddled with cays and hideaways — and once the crossroads of a major sea-trading route — the British Virgin Islands were an attractive locale for pirates and privateers.

Just about every anchorage in this archipelago has a story from the heyday of pirate lore, including the small and desolate island of Dead Chest, where, according to legend, 15 men and at least one bottle of rum were marooned by Captain Blackbeard after his crew attempted a mutiny. As the story goes, most of the men’s bodies washed up in Deadman’s Bay, an eastern cove off nearby Peter Island, after they tried to make the treacherous swim to the larger island.

Tales of buried treasure abound from the adjacent Norman Island, which is perhaps most famous for being the inspiration behind Robert Louis Stevenson’s novel Treasure Island. According to legend, caves lining the island’s western bight served as hiding places for gold and other riches plundered from state coffers, including holdings from the Nuestra Señora de Guadalupe, a Spanish galleon whose crew mutinied off the coast of North Carolina in 1750. First a retreat for sea rovers looking to stow their loot, Norman Island soon became a hotspot for other assailants looking to steal the spoils of their competitors.

Photo: Soggy Dollar Bar

Photo: Soggy Dollar Bar

Though today’s Norman Island is privately owned and mostly uninhabited, travelers from near and far can drop an anchor in The Bight Bay and pay a visit to Pirates Bight Bar, Restaurant, and Gift Shop, known for its crispy calamari, fresh lobster, and tuna carpaccio.

Further north sits the BVI capital of Tortola, which preserves the remnants of its pirate-laden past through aptly-themed landmarks and establishments. One such attraction is Soper’s Hole Marina, the deep harbor where Blackbeard once moored and now the home to Pusser’s, a prized watering hole and purveyor of the storied British rum bearing the same title. On the beach adjoining nearby Nanny Cay, Peg Leg Landing specializes in eclectic seafood and sweeping views of the Sir Francis Drake Channel, named after the renowned English privateer who famously plied the region’s waters looking for Spanish ships in the name of the Queen.

While on Tortola, visit Smuggler’s Cove, a secluded bay harboring one of the island’s most pristine beaches. Visible from the tip of the cove, and rising from the sea on the northern horizon, is Jost van Dyke, named after the Dutch privateer and pirate who settled there and allegedly used the island’s natural tide-fed pools for his annual bath. Travelers who take the ferry northward will find plenty of ways to reminisce on the legends of yore while imbibing on Voodoo Juice from Corsairs Beach Bar & Restaurant or the celebrated Painkiller cocktail from the Soggy Dollar Bar.

Photo : Nwmangum Wikimedia Commons / CC BY

Photo: Nwmangum Wikimedia Commons / CC BY

On the topside of Beef Island just east of Tortola is Trellis Bay — the reputed lair of the famed and feared Black Sam Bellamy, also known as the Prince of Pirates. From this stronghold, Bellamy resupplied his legendary 300-ton sailing warship, the Whydah, with fresh meat from wild cattle on Beef Island before scouring the region to relieve scores of unfortunate ships from their gold, silver, jewels, and valuable navigational instruments. Bellamy’s short, albeit prolific, career ended abruptly during a northbound expedition, when the Whydah sunk, along with its treasure, in the stormy seas off of Cape Cod. (The ship and its bounty were recovered by treasure hunters in 1985.)

Of all of the BVIs, the north-lying island of Anegada perhaps provided the most opportune site for beachcombers, wreckers, and beached buccaneers of yesteryear. A coral atoll protected by one of the biggest barrier reefs on the planet, it is a graveyard of countless shipwrecks from the past several centuries. Take the ferry from Tortola to visit Pomato Point, a restaurant and museum containing collections of artifacts, including gin bottles, apothecary jars, coins, sword handles, naval buttons, and an old treasure map recovered from the wreckage.

US Virgin Islands

Photo : Mali via Wikimedia Commons / CC BY

Photo: Mali via Wikimedia Commons / CC BY

With little to no threat of being boarded, today’s seafaring travelers enjoy smooth sailing along the Sir Frances Drake Channel, which runs along Tortola’s south belly and separates the BVIs from the US Virgin Islands.

Some of the most infamous figures to establish their pirate bases in the USVIs include Bartholomew Sharp, Captain William Kidd, Anne Bonney, and Captain Edward Teach — better known as Blackbeard — who was said to instill fear in his enemies by intertwining lit candles into his beard.

In the Dutch colonial city of Charlotte Amalie on St. Thomas, standing sentinel on the highest point of Government Hill, rises the stone lookout known as Blackbeard’s Tower. Believed to be Blackbeard’s center of operations during his legacy in the early 1700s, the watchtower may have been used to plan assaults and search for passing ships. While the columned fortress is currently undergoing repairs in the wake of Hurricane Irma, visitors can still savor the panoramic views surrounding it while admiring the world’s largest collection of life-sized pirate sculptures.

Photo: Pirates Treasure Museum

Photo: Pirates Treasure Museum

During the peak of Caribbean piracy, Charlotte Amalie remained a haven for an array of questionable characters who bribed the local government in exchange for safe harbor. But to the unexpected chagrin of two legendary pirates, Jean Hamlin and Bartholomew Sharp, an English officer snuck aboard and sank both their ships, complete with a cache of silver, to the bottom of the harbor where the wreckage remains today. This legend, along with other colorful tales of shipwrecks, treasure, and debauchery, can be explored in full detail through the interactive exhibits at the Pirates Treasure Museum.

Elsewhere in the USVIs, there are a number of beaches where travelers can picture pirate life and search for gold doubloons unearthed on sandy shores. Make time for beautiful Trunk Bay on St. John, as well as Rainbow and Buccaneer beaches on St. Croix. You could be walking in the footsteps of history’s most notorious marauders, your skin made swarthy by the Caribbean sun.