Between the late 1600s and mid-1700s, the Atlantic was a hotbed of pirates and privateers, and it wasn’t always easy to tell the difference between the two. Bermuda was a perfect base for high-seas adventurers, with pirate ships sailing off into the sunset, plundering treasure-laden vessels from across the seas.
Pirates or Privateers? Privateers were technically “legal” pirates, licensed by the Crown to loot enemy ships. It was all very official (on paper, anyway). But let’s be honest, the line between “pirate” and “privateer” was about as clear as a foggy morning on the ocean.
Bermuda’s ships were like the sports cars of the sea—fast, nimble, and handled by some of the best sailors around. No wonder Governor William Browne boasted about their superiority. These vessels, ranging from tiny 18-ton boats to sturdy 100-ton ships, were built for action and could outrun almost anything that dared cross their path.
One of the most infamous pirates with ties to Bermuda was Nathaniel North—a swashbuckler whose adventures rivaled the likes of Captain Kidd and Henry Morgan. North started out learning from some of the most feared pirates of the time and soon made a name for himself in the Indian Ocean.
Another Bermudian scallywag, Nicholas Trott, earned himself the dubious title of “the greatest pirate-broker in America” according to the Governor of New York. Other names like John Dickinson, William Outerbridge, Richard Gilbert, and Robert Tucker also sailed Bermuda’s seas in search of treasure and glory. These pirates and privateers have left their mark not only on Bermuda’s history but also in the local names and places you can still find today.
Add these fun pirate-inspired activities to your itinerary:
Climb Abroad Calico Jacks Pirate Bar
We all know the pirates enjoyed their rum so for a lively libation don’t miss Dockyard's floating slice of pirate paradise. Located right on the water, this seasonally operated lively bar offers a swashbuckling good time with incredible ocean views, cold drinks, and a fun, laid-back atmosphere.
Whether you’re in the mood for a famous Bermuda Rum Swizzle, island music, or simply soaking in the island vibe, Calico Jack’s is the perfect spot to kick back after a day of exploring. Climb aboard, enjoy a drink with fellow travellers, and don’t forget to snap a selfie with the pirate ship backdrop!