Interlude: The Colors
Once a group of sailors decides to go on the account, there are two pieces of business that must be resolved. One is to write up a set of articles, and have all the willing hands sign them; the other is to choose a pirate flag for hoisting atop the mainsail. When it comes to the latter question, there are a number of points to consider regarding what the flag means and what kind of message it conveys to friends and foes alike.
For the following descriptions, please refer to the “Jolly Roger Gallery” on Wikipedia:
The basic pirate flag usually has a black background, combined with a skull and something else. Take, for example, the flag attributed to “Black Sam” Bellamy and Edward England, the old skull and crossbones, or the skull and crossed swords of John “Calico Jack” Rackham. These ones certainly convey that the vessels flying them belong to pirates, but they're not too specific beyond that.
Other flags use more detailed and gruesome images of death. The first flag believed to have been flown by Bartholomew “Black Bart” Roberts, for instance, depicts him and a spear-carrying skeleton holding an hourglass, implying that time is short for those who defy him and his crew. The image associated with Edward “Blackbeard” Teach shows another skeleton, this one apparently having horns, that holds an hourglass in one hand and a spear, ready to shed the blood of a hear, in the other.
Some pirates have a much more specific meaning, one that makes it clear just who the pirate's enemies are. Another flag attributed to Bartholomew Roberts depicts the pirate himself standing atop two skulls, beneath which are written ABH and AMH. The letters are thought to stand for the phrases “A Barbadian's Head” and “A Martinician's Head,” making it clear that Roberts had some kind of quarrel with the people of those islands.
From this point onward, the different flags present variations on the same theme. Some used red for the background, instead of black, or added red or yellow as colors for the images. Red, it should be noted, typically implied that there would be noted quarter asked or given during a battle, and sometimes flags of this color would be run up after the start of an engagement, when a prize made it clear that it would not cooperate. A Frenchman, Captain Mission, even flew a white banner embroidered with the phrase A Deo a Libertate in Latin, meaning “For God and Liberty.”
Whatever image the PC's decide to use for their flag, this gives them a good opportunity to be creative and have a little fun. Perhaps an artistic player could sketch this jolly roger, helping to make a distinct impression for when the time comes to run up the colors.