Didn’t you just do bandits? What’s the difference?

In the last entry in this series I covered bandits, which I defined as those who perform opportunistic attacks on land-based travelers far from centers of power, primarily via ambush. By contrast, pirates usually operate by large crewed vehicles and attack other such vehicles while they are traveling through a region that is not easily traversed or survived without a vehicle, such as oceans, silt seas, the sky, giant ice slicks, or vast dusty wastelands.

So, in the spirit of celebrating the new shoreline and sea adventure themed 5e book, without further ado, I give you:


Pirates, be they sea pirates, sky pirates, space pirates, or Mad Max style wasteland pirates, not only threaten the party’s wealth, but their ability to travel in relative safety as well. Due to the difficulties of moving people and materials in whatever the pirates’ domain may be, the vehicles themselves are often at least as valuable as the cargo within, and these vehicles—especially in a fantasy world—cannot often simply be carried away or towed, and thus require crews to operate them.

Reasons for Pirates to take Captives

     Recruitment. Often pirates will press any survivors of an attack into service as part of the crew, generally under careful watch and harsh discipline, but it is a better option for all parties than leaving potential recruits adrift, at least until they’ve proven to be a problem. Usually they will send the new recruits in first in boarding parties, which solves several security concerns during an attack, but those who survive are generally rewarded with a crew member’s share of earnings. Some ships will require a crew member serve until their share reaches a certain size, but after that will freely allow the individual to leave if they see fit. Furthermore, if the ship they attacked is taken, a crew must be assembled from the attacking ship’s crew to take it back to a friendly port, leaving the main vessel’s crew shorthanded. This is by far the most common reason for pirates to take captives.

     Slave Trade. Well-manned pirate vessels may prefer instead to sell their captives if there are ports amenable to slave trading in their area. This is not as common as one might think, however, as traditional pirates know they may well be taken captive themselves if a fight goes badly. As a result this is usually requires a port controlled by a nation that supports slavery, and either privateer ships loyal to that crown or free traders who keep their pirating activities quiet or far from home port.

     Prisoner Exchanges. Privateers and pirates alike may take captives from civilian or naval ships loyal to a nation in order to trade them for prisoners taken by that nation. Captains and other ship’s officers will likely be more eager to engage the enemy if they know that there is a good chance they will be freed once their allies take a ship from the enemy.

Pirate Capture Tactics

     Surrender. For the most part, pirates take their captives simply by offering quarter to the losing side once the battle is clearly won. This reduces casualties on all sides and also maximizes the chances of recovering cargo and vessels intact. If the party are not part of the command structure of the vessel, they may have no choice but to surrender simply because the crew of the ship has surrendered and the party alone cannot pilot the ship.

     Physical Restraints. In order to speed a boarding action along to the point of the losing side surrendering, using nets or other forms of restraints, such as bolas, or wands of web for well-to-do pirates, can decrease the effective fighting force of the boarded vessel.

     Magic. Well equipped vessels may be staffed with spellcasters than can put enemies to sleep or compel them to cease hostilities or become cooperative. This is especially effective if directed at the officers of a vessel.

     Kidnapping From Land. Most often, those taken from ashore are press ganged while heavily intoxicated (or drugged, or ensorceled), or otherwise subdued by covert means promptly before the vessel leaves port. If they are taken instead by force, this functions more like raiders, who I will detail in greater depth in a subsequent entry in this series.

Escaping from Pirates

     Wait. Often captives of pirates can escape simply by cooperating and surviving long enough. Pirate ships are surprisingly well organized and have a strong sense of democracy regarding anyone who has fought with the crew long enough to be deemed trustworthy. In particularly bloody seas, becoming part of the crew may rapidly result in the party achieving important positions on the ship, possibly even becoming the captain if the previous one is killed.

     Stealth. When a vessel is close enough to a location where people can survive, clever and sneaky characters might be able to slip overboard or commandeer a launch boat or the like to escape. This is tricky if the ship is docked on an island or the like, as the party may have to lie low until search parties give up, and the party might be split if not everyone can get away before the ship departs.

     Bargaining. Promise of riches go a long way when negotiating with pirates. If you have some way of ensuring a large ransom is paid if you are delivered to port (or can trick them into believing you do), they may simply keep you under watch until they can trade you for the promised reward.

     Force. Coordinating a group of captives who are covertly freed from restraints to not defeat the ship’s crew, but merely fight to take over a boat to row to shore in under cover of darkness might be feasible, but this would be a very unconventional combat in many systems, as the objective is escape rather than overcoming the foe.

     Mutiny. This option is precarious as the punishment for failed mutineers is usually something comparable to summary execution, and it requires a great deal of discontent by the original crew as well, in order to have sufficient force to take control. Failed mutineers may be shown clemency by being stranded on an uninhabited island rather than being thrown overboard at sea or the like, which may provide an opportunity to introduce a party of sailors to an ancient dungeon or the like, however.

What’s in it for the Party?

     Riches. Simply abiding as part of a successful crew will eventually net the party a measure of wealth when they finally have the opportunity to go ashore and leave the crew. If they simply sneak ashore, they could potentially pocket whatever they can carry with them as well. If they take control of the ship itself, they will have whatever is contained within its holds.

     A Ship. If the party can take control of the vessel itself, they will have obtained one of the most valuable possessions in any area where travel by vessel is necessary.

     Loyalty. Whether by earning a place of authority on the ship, succeeding in mutiny, or leading a group to escape, the party can easily earn dedicated loyalty and no end of small favors from those who now trust them or owe them their lives. In addition to simple crew members, this may also include a strange old man who knows important secrets, a cleric of a sea deity who can grant boons or blessings, or other such notable npcs.

     Exotic treasures. Especially in a fantasy world, some of the most valuable items on a pirate ship are not the barrels of salted meat or rum in the holds, but smaller special items. These might be enchanted weapons, crystal arrays that influence the weather, a magical compass or map to a lost treasure, gems that summon elementals.

     Bounties. If the ship can be taken by force, there are likely to be large bounties on the heads of notorious pirates among the crew that the party can cash in on if they know what port to travel to to claim them.

Leave a Reply

Your email address will not be published. Required fields are marked *