Captain: The ultimate authority upon the vessel, elected by the crew. Expected to be a skilled and fearless warrior, as well as an expert in navigation and sailing, but their most important role is that of a larger-than-life figurehead inspiring or terrifying the crew as necessary. The terms Master and Skipper are synonymous, and a Commodore commands multiple ships.
First Mate: The officer second in command to the captain. Typically oversees all day-to-day operations in addition to the wellbeing of the crew and vessel, and to this end gives orders to the boatswain. On most ships, the quartermaster becomes the de facto first mate.
Quartermaster: The elected officer in charge of recording and distributing supplies and accomodations. Given the importance of food and plunder to a freebooter, quartermasters are often accorded considerable prestige and authority, nearly as much as that of the captain. Merchant ships might also have a purser, specializing in the handling of money.
Boatswain: Pronounced 'bosun,' this is the officer responsible for inspection and maintenance of the vessel. Reports directly to the captain or first mate, and typically assumes hands-on authoritative duties, such as the handling of sails and disciplining of the crew.
Sailing Master: The officer responsible for sailing and navigation, managing maps and reckoning instruments. Difficult yet necessary work, given the inaccurate nature of sea charts.
Ship's Wizard: Not found on every ship, but highly valued for their vast utility and decisive role in battle. Their mere presence aboard a ship lends considerable dread.
Master-at-Arms: The officer whose expertise lies in the operation and maintenance of the ship's armaments, such as cannons and ballistae. Also responsible for drilling the crew in their use.
Carpenter: A vital role, the carpenter is responsible for repair of the hull and masts of a ship, and often conducts inspections to keep the vessel seaworthy.
Surgeon: The ship's doctor, typically well versed in physical wounds and infection. Often a dual role with the position of carpenter, due to the use of the saw. Might also be a barber.
Mates: The apprentices of the various officers, who often perform the more mundane duties of the position, and might assume their master's role if necessary. Also usually charged with various key duties, such as hoisting the anchor, keeping nightly watch, or acting as a steersman (the helmsman of the ship, or the coxswain of a boat).
Riggers: Sailors with slightly more prestige, trusted to work aloft in the rigging. A dangerous position, navigating slippery swaying ropes and spars.
Swabs: The basic role of most freebooters, responsible for all aspects of daily work aboard the ship, such as managing lines, hauling cargo, and of course swabbing the deck.
Cabin Boy/Girl: A trusted youth who acts as a servant to the captain and officers. Often exempt from regular duties.
Powder Monkey: A role filled by those with small quick hands, such as children and halflings. They provide gunpowder to cannoneers during battle. Goblins, though awful seamen in nearly every respect, make the finest powder monkeys and cannon crew.
Catamaran: A vessel peculiar to tropical islanders, consisting of two parallel hulls supporting a platform. Usually used by islanders for transport, fishing, and cargo, as no other vessel can compete with its speed, shallow draft, and minimal use of resources. Despite its delicate frame it may be used by tribal warriors for piracy and raiding.
Felucca: A fast, comfortable vessel with one or two masts, lateen-rigged. May be used for fishing, running cargo, or as a pleasure barge, but is rarely used for raiding. Thanks to its shallow draft, it can move from coast to river with the use of sails and oars.
Schooner: A vessel with two or more masts, entirely fore-and-aft rigged. It is exceptionally fast, and can sail very close to the wind. It is used for fishing or as a fast merchant vessel, relying on speed and maneuverability rather than any armaments. Typically a boat, but a large ship can be rigged as a schooner.
Sloop: A small, simple, yet quick sailboat with a single fore-and-aft rigged mast. Extremely common and used for personal transport and fishing. Such a vessel used for a ship's boat may be referred to as a cutter.
Brig: A ship with at least two masts, both square-rigged. The workhorse of the Shackles, very common as a quick merchant vessel and favoured by corsairs for its light weight and capacity for heavy armament.
Brigantine: A small two-masted ship similar to the brig except square-rigged on the foremast only and featuring a smaller hull, trading armaments for greater maneuverability. Very common across the Inner Sea Region as an armed merchant, naval escort, or corsair ship.
Caravel: A small ship with multiple lateen-rigged masts, very popular for fishing and cargo running, but occasionally outfitted for raiding.
Cog: Perhaps the most basic type of ship, the cog has a single square-rigged mast. It typically has a flat bottom for ease of cargo handling, and high sides to defend from sea raiders.
Galley: A ship propelled by lateen sails and multiple tiers of oars. Thanks to its shallow draft, maneuverability, and necessary manpower it is much favoured by slavers, and is sometimes employed as a coastal warship outfitted with catapults and a bow ram. Due to its low freeboard, it tends not to fare well in high seas, but can navigate shoals and rivers. It may be referred to by the number of tiers of oars as a monoreme, bireme, trireme, or quadrireme, and very heavy galleys may be referred to as dromons.
Galleon: A heavy, multi-decked ship with three or more masts and towering fore- and sterncastles. They are favoured as armoured merchant vessels and make very effective light warships. Corsairs who sail a galleon are well respected for their capability and their brazen attitude. A galleon outfitted with oars might be referred to as a galleass. A heavier, older design is referred to as a carrack; this slower top-heavy variant is better for ramming and boarding, but is vulnerable to cannonfire.
Junk: A vessel named for its junk-rigging, its sails supported by long wooden poles. A Tian design, providing ease of use and lower maintenance. Junks range in size from small houseboats to imposing warships, but tend to be slow, sturdy flat-bottomed vessels often used for hauling cargo.
Longship: The ship of the Ulfen, reknowned for its use in raiding. It is characterized by the long, narrow open hull, single great square sail, and oars along its length. It is light with a shallow draft, lending it the ability to make beach landings, navigate small rivers, and allow for portage. The smallest is a Karvi, used for trading and fishing. The Snekkja is a light vessel used for cargo and raiding. The Skeid is larger and faster, and the Drakkar is a grand warship carved with intricate designs.
Battleship: Also a 'ship of the line' or 'line-of-battle ship', this vessel is designed to maximize firepower, with 40 or more cannons or ballistae, multiple catapults, and often 200 fighting sailors. Typically operates as part of a fleet under a commodore for warfare, expedition, and merchant escort. Very rarely engaged by any lone corsair vessel.
Catawar: A scaled-up variant of the tribal catamaran, consisting of two hulls supporting a vast platform rigged with lateen sails. Each hull can be fitted with 100 oars, allowing for transport of large numbers of marines, archers, and siege engines while retaining maneuverability. Catawars are often used for harbor protection or in blockades.
Frigate: The smallest of ships commanded by captains of naval empires, the Frigate has three or more masts, all square-rigged. It is fearsome in battle, boasting considerable speed and firepower. It may be outfitted with multiple decks of guns or ballistae and a bow-mounted catapult. A frigate requires a large crew and may be manned with highly trained marines.
Man-o'-War: These sailing behemoths are the height of military naval engineering. Generally fleet flagships commanded by admirals, men-o’-war rarely leave port with fewer than a dozen other warships accompanying them. With up to 50 guns on three or four decks, half a dozen heavy catapults, and hundreds of fighting sailors, marines, clerics, and wizards, these intimidating ships are virtually unstoppable.
Dreadnought: Any ship superior to all other vessels in its waters, such as the Chelish Man-o'-War Abrograil's Fury or the Hurricane King's flagship the Filthy Lucre.
Hulk: Any ship which is afloat but unable to sail due to damage or deliberate conversion of an obsolete vessel. They might be used as storage, housing, markets, prisons, gambling houses, Besmaran chapels, quarantine hospitals, or shipbuilding platforms.
Tender: Any boat or ship used to support other vessels, generally by transporting supplies and personnel. These may be harbour boats or a ship's boat, and are sometimes referred to as bumboats or jolly boats.
Various small craft: Dinghies are very small rowboats which may have a small sail. Gigs are propelled by multiple sets of oars. A pinnace is a large rowed tender or small sailing boat, and is favoured by ferrymen and smugglers. A longboat or launch is the largest boat which can be carried on a ship, and may be rowed or fitted with a mast. A barge is any low, flat-bottomed transport vessel, typically found on rivers and shallow coasts. A cutter is a ship's boat with a single mast rigged fore-and-aft.
Certain things are common knowledge to seamen of the Shackles.
What government exists broadly across the Shackles is highly decentralized, permissive, and meritocratic. If you have a ship, you may proclaim yourself a Free Captain. The most powerful Free Captains are those who have built or seized control of major ports and fleets. These Pirate Lords have formed a loose alliance known as the Pirate Council, and they elect a leader known as the Hurricane King. For the last 40 years, the title has been held by Kerdak Bonefist, the hulking reclusive human Pirate Lord of Port Peril.
The enemy of all true brethren of the Shackles is the imperalist nation of Cheliax. The islands have been protected from invasion thanks to the Eye of Abendego, but the Chelish Navy is always seeking an opportunity.
The archipelago now known as the Shackles was once the ancient kingdom of Ghol-Gan. The cyclopes of that vast nation resorted to dark rituals, debauchery, and worship of alien horrors. All that is left of them are their accursed ruins.
Rum is the blood of the Shackles. You will find it everywhere, prized for recreation, medicine, nutrition, and trade. For many it is the only thing keeping them upright. It has many varieties such as white, spiced, dark, and black, and there is a type of overproof black rum unique to the Shackles, but Shackles Rum is not meant to be consumed straight. A more pleasant and economical mix is that of grog: three parts water, one part rum, with a strong squeeze of citrus. Grog is important for avoiding the terrible plague of scurvy.
Many languages are spoken across the Shackles. The lingua franca is of course Common (that is, Taldane), but nearly as widespread is Polyglot, a patchwork trade language cobbled together from countless Mwangi tongues. If a sailor does not speak one, they will certainly understand the other. Other useful languages are Tengu, Osiriani, Tianese, Skald, and Thieves' Cant. Some obscure languages which may be encountered include Aquan, Varisian, and Halfling. Ruins of the savage empire of Ghol-Gan make use of ancient Cyclopean script, and the Kuru of the Cannibal Isles have their own brutish language.