Now, for most of the modern games we play, you start with a small ship. Sure, there were people who invested in Pirate and Privateers, and some rich people just decided to go on an adventure by buying or building a Pirate or Privateer Ship. But if you have that much money or have that much influence to get someone to invest in you, you should realize that there are better ways other than Piracy to obtain adventure. Most pirates were sailors of a peasant background. They didn’t have money or have the influence to get someone to invest in them. So they simply just stole a ship.
During the mid 1600s, the island of Hispaniola was infested with buccaneers. These buccaneers were quick to turn robber or pirate. The Spanish got to a point were they actually decided to try and do something about it. The Spanish made an effort to drive the buccaneers out of their land homes. It somewhat worked, but the after effect created a plague of buccaneers on the high seas as pirates. The buccaneers hated the Spanish, so they would especially target Spanish ships. But how they got their ships is a common example of how the poor obtain ships.
The first thing to happen would be that an organization would be formed. Somewhere from 15 to 75 men (or even smaller, and most of the time, they were small numbers), would get together, all agree they would engage in piracy, create a contract, agree to the contract, and elect a captain. Pirates were very democratic. These men would gather together any type of weapon they could make or steal. Tools were commonly used, like axes. Sometimes even a simple, as a club would be employed as a weapon. But more common things like knives and machetes were commonly used. The machete is sort of a brother to the cutlass, except the cutlass is designed for use at sea. On a rare occasion, someone might scrounge up a pistol or musket with shot (most likely stolen). Modern piracy’s origin comes from these men.
The next step would be to find boats. Fishermen commonly had boats, and a band of men could easily overwhelm a lonely fisherman or two. If the group of Pirates has an amount of money, they could buy a boat (or they could possible steal the money, but why waist time, just steal the boat). With these boats, the Pirates could possibly sail to other areas, and steal more things, and use them in the eventual stealing of a ship. It might take a month of a few months to find a ship vulnerable enough for them to attack. Meanwhile, they could steal more weapons, steal bigger and/or better boats, possibly add to their numbers, and maybe find out when a ship would be sailing by that they could take.
When they find a ship they can take, they will attack. The Pirates will most likely attack when the crew is at it’s least prepared time, and when they least expect it. Most likely they will attack at night, so they can row over to the ship under cover of darkness. It would also be good if when they attacked, that there were no villages, people on shore, or other vessels around, so there were no witnesses, or no one to support the crew of the vessel being attacked. So they would row quietly in the middle of the night to the ship. The more numbers a crew had, the more overwhelming the attack would be and seem like. These men when they got on deck would try to kill or capture any guards as soon and as quietly as possible. The goal was to try and kill or capture as much crew as possible before the crew could rally to repel an attack. Sometimes the crew never rallied due to the suddenness of an attack, and how quickly the Pirates would go through a ship and secure it. But more often then not, the Pirates failed, and were lucky if they escaped. Remember, the crew most likely have in their possession, pistols, muskets, cutlasses, and more actual weapons, not just tools turned to weapons like the Pirates most likely had.
If the Pirates were successful, it was their call on what to do with the crew. They could just leave them on shore, but that would still leave witnesses. They could try and maroon them. Marooning someone doesn’t mean putting someone on an island with trees, and vegetation; usually marooning would be putting someone on a sand bar at low tide, or a small parcel of sand that had no vegetation, and either they would most likely starve to death on the small sand island, or drown when high tide came along on the sand bar. This makes the odds of having living witnesses from the ship unlikely, if didn’t kill them by your own hand. Of course, if you don’t have time, you could just kill the crew yourself. Slavery was common, but can you hold on to them long enough to sell them, and have to feed them? Also, these slaves could run and be witnesses. When being a Pirate, you were always thinking of what your action’s repercussions could be later.
After the Pirates have a ship of some sorts, and disposed of the crew, what was next depended on the situation. Usually, the ship they stole was a Pink, Sloop, or some sort of ship. The ship was probably a merchant ship, because their crews aren’t exactly as good as a fighting ship’s. The ship that was stolen has a good chance not to have cannon, or even swivel guns. So the next step might be to steal another ship that has what you want for raiding out at sea. At least when attacking the next ship, they will most likely have better weapons that the last crew of the ship had. Most pirates wanted to work up to a ship that was fast, heavily armed, and at the sight of it, could seduce a merchant into surrender. From that point, a Pirate crew would start its career into becoming a thorn in the civilized world’s side.