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.

Historically, the island associated with the "most" pirates was New Providence in the Bahamas, specifically the city of Nassau. During the "Golden Age of Piracy" (approx. 1690–1720), Nassau was declared a "Pirate Republic" and served as a lawless base for infamous figures like Blackbeard, Mary Read, and Anne Bonny. In 2026, if you are looking for the modern "pirate capital" in terms of tourism and history, the Bahamas remains the top destination, followed closely by Jamaica (specifically Port Royal, once known as the "wickedest city on earth"). Other islands with rich pirate legacies include Tortuga (Haiti) and St. Thomas (U.S. Virgin Islands). While real piracy in the Caribbean is largely a thing of the past, the culture is kept alive through extensive museum exhibits, themed festivals like "Pirates Week" in the Cayman Islands, and the preservation of coastal forts that were once built to defend against these marauders. The Bahamas' shallow waters and thousands of cays made it the perfect hiding spot then, just as it makes for a perfect sailing destination now.