Finding Pirates in the Caribbean

During the golden age of piracy in the 17th and 18th centuries, port towns on the islands of Jamaica, New Providence and Tortuga became ideal havens for such buccaneers and privateers as Blackbeard, Calico Jack and Henry Morgan. They were all keen to intercept loot being shipped from the Americas back to Europe.

Many Caribbean islands play up their possible links to pirate history. You can find references to piratical heritage on almost every island from Aruba to Trinidad, and trinket vendors at many cruise-ship ports are happy to sell you a Jolly Roger magnet, mug or T-shirt.

But was Edward Teach, aka Blackbeard, ever really there? It’s hard to verify. Caribbean pirates were not easy to pin down and spent most of their time at sea. So how does a landlubbing-pirate-treasure-seeking tourist sort out what’s real and what’s not? We’ve rounded up a few of the best places in the Caribbean to find authentic pirate experiences.


Nassau, Bahamas
Nassau on the island of New Providence was an ideal base of operations for the nefarious denizens that flocked there. The harbor waters were too shallow for large man-of-war ships, but were deep enough for the fast, shallow-draft vessels preferred by pirates. The many islands, coves and hidey-holes nearby were also ideal for hiding misbegotten loot. Such pirate rock stars as Charles Vane, Calico Jack Rackham and Teach, as well as women pirates Anne Bonny and Mary Read, were known to drop in on occasion.

Nassau proudly displays its (mostly) real pirate history, and you’ll find plenty of historic walking tours, boat cruises and bars to carouse in. Highlights include Pirates of Nassau, a playful interactive museum that re-creates the bawdy heyday of piratical lore, and Blackbeard’s Tower, which may or may not have been built as a lookout by Teach himself.

Port Royal, Jamaica
The Jamaican town of Port Royal was once the pirate capital of the Caribbean and it was the hub of Britain’s naval operations in the West Indies for more than 200 years. Fabled pirates such as Henry Morgan, Teach and Christopher Myngs are said to have spent time there.

Several earthquakes since the 17th century knocked major portions of the city into the sea. There are plans to redevelop what is mostly a ramshackle fishing settlement for tourism, but little has materialized. Nonetheless, real pirate history buffs consider Port Royal a must-see. Visitors should make a beeline for the Maritime Museum and Fort Charles (circa 1655), the only of the town’s original 6 forts still standing.

Tortuga Island, Hispaniola
Tortuga, a tiny island off the northwest coast of Haiti, became one of the most notorious pirate settlements in the Caribbean when French and Spanish buccaneers set up shop in the mid-17th century. Serious pirate historians put the island high on their travel to-do lists. Intrepid visitors should find the northern coastal town of Port de Paix. From its primitive airport, take a ferry for 6 miles to the 25-mile long, turtle-shaped atoll. A handful of budget lodging options are available across the rocky island. Visitors will find pristine beaches, caves to explore and the remains of a couple of forts.

Cruise on a Tall Ship
You can’t understand a pirate until you’ve sailed a mile on his boat. So why not try a tall ship cruise on a large, traditionally rigged sailing vessel? The brigantine, schooner and frigate were pirate favorites. Many Caribbean islands offer day and sunset cruises on tall ships, some even with pirate themes. Such companies as Windjammer and Star Clipper offer multi-day tall ship cruises through the Caribbean with stops at famous pirate haunts like Nassau and Dominica, where much of the Pirates of the Caribbean films were shot.

Cayman Islands, Pirates Week Festival
Here’s where you can don an eye patch, down some rum and yell “Ahoy, me hearties!” at passersby. The Cayman Islands’ Pirates Week Festival has been a hit every fall for 33 years. Eleven days in November are filled with music, street dances, treasure hunts, food, parades, sports events, Heritage Days, costume competitions, even a “surprise” mock pirate invasion at George Town harbor.


Travel writer Trisha Creekmore has traveled to more than a dozen Caribbean islands. While she has yet to discover real pirate treasure, she has slept in several cities where Blackbeard has also supposedly slept.