In the old pirate movies, there would always be a point when the hero and the villain faced-off against one another with swords. They would duel with one another if you will. First, the hero would seem to be winning and then the villain, usually through some foul trick, would get the hero against the ropes. Finally, with some slick move or simply a faster blade, the hero would make the killing stroke to send the villain to his doom.
This is all complete fantasy; real fights in the age of piracy didn't happen anything at all like this. In order to learn about the true art of pirate sword fighting, we must study three things - pirate swords, pirate crewmen, and pirate techniques.
The most common type of sword associated with pirates, privateers, smugglers, and their ilk is the cutlass. The cutlass is a sword with a short, curved blade that's sharpened on one edge and at the point. It could be used as a thrusting weapon, but it was most often employed in slashing attacks. Additionally, a cutlass has a heavy blade making it excellent for chopping through dense jungle, cutting away the ropes on a broken spar, or killing troublesome foes; it was a tool as much as a weapon. While other swords of the time period, such as the rapier and the court sword, were used by some individuals, they weren't nearly as common as the cutlass.
The men who became crew members on pirate ships were tough sailors who were looking for a better life. Whether they were recruited in a shady tavern in the Caribbean, volunteered to leave a captured merchant ship's crew, or were originally victims of a press gang, pirates were usually tough men from the lower social classes. These weren't men of leisure; they worked hard to support themselves and their families. They would've had neither the time nor the money for private lessons from a sword master or to attend a school of arms. Sword fighting and practicing it were done by military men and by those of financial means who wished to pursue such skills. Certainly, there were pirate captains and perhaps officers who had seen service in the military and/or had come from wealthy families, but surely these men were more rare than common on board a pirate ship.
Pirates are people who would launch attacks and rob ships at sea. Pirates, like most other robbers, sought to take their prizes without fighting. The most common technique used by pirates was to approach a merchant ship flying a friendly flag and then when nearly upon the ship, changing to the skull and crossbones or black flag to show their true intentions. The black flag was a sign to the captain and crew of the merchant ship that everyone on board would be spared if the merchant captain lowered his sails, dropped anchor, and allowed the pirates to take what they wanted from his ship. The black flag was usually only displayed for a limited time, if the merchant captain took too long to surrender his ship (or showed defiance); then the pirates would raise a red flag indicating that when they took the ship, they would leave no survivors. Fighting on-board a ship was a messy, close-quarters affair. Punching one target in the face with the cup hilt of the cutlass while short-thrusting its point into the throat of another opponent was likely common when murderous pirates fought simple merchant sailors in those harsh times.
When you look back at a pirate’s life, it was one of many travels, fighting, and staying alive on the open seas.