Corsair Pirate Ship:
With its square-rigged foremast and fore-and-aft sails on its main mast, the brigantine was fast, easy to maneuver and had twice the cargo space of a sloop. No wonder it became the favorite vessel of pirates of the Caribbean. A typical brigantine carried as many as 100 pirates and mounted enough cannon to intimidate any possible target.

Privateers:
Piracy in the Caribbean came out of the interplay of larger international trends and the use of privateers was especially popular. The cost of maintaining a fleet to defend the colonies was beyond national governments of the 16th and 17th centuries. Private vessels would be commissioned into a 'navy', paid with a substantial share of whatever they could capture from enemy ships and settlements, the rest going to the crown. These ships would operate independently or as a fleet and if successful the rewards could be great —this substantial profit made privateering something of a regular line of business; wealthy businessmen or nobles would be quite willing to finance this legitimized piracy in return for a share. The sale of captured goods was a boost to colonial economies as well.

Buccaneers:
Specific to the Caribbean were pirates termed buccaneers which arrived in the 1630s. The original buccaneers were escapees from the colonies; forced to survive with little support, they had to be skilled at boat construction, sailing, and hunting. These skills transferred well into being a pirate. They operated with the partial support of the non-Spanish colonies and until the 1700s their activities were legal, or partially legal and there were irregular amnesties from all nations.

Traditionally buccaneers had a number of peculiarities. Their crews operated as a democracy: the captain was elected by the crew and they could vote to replace him. The captain had to be a leader and a fighter—in combat he was expected to be fighting with his men, not directing operations from a distance.

Spoils were evenly divided into shares; when the officers had a greater number of shares, it was because they took greater risks or had special skills. Often the crews would sail without wages—"on account"—and the spoils would be built up over a course of months before being divided. There was a strong esprit de corps among pirates. This allowed them to win sea battles: they typically outmanned trade vessels by a large ratio. There was also for some time a social insurance system, guaranteeing money or gold for battle wounds at a worked-out scale.

In combat they were considered ferocious and were reputed to be experts with flintlock weapons, but these were so unreliable that they were not in widespread military use before the 1670s.

The end of the classic age of Piracy:

The decline of piracy in the Caribbean paralleled the decline of mercenaries and the rise of national armies in Europe. Following the end of the Thirty Years' War national power expanded. Armies were codified and brought under Royal control and privateering was largely ended; the navies were expanded and their mission was stretched to cover combating piracy. The elimination of piracy from European waters expanded to the Caribbean in the 1700s, West Africa and North America by the 1710s and by the 1720s even the Indian Ocean was a difficult location for pirates.