Dungeons and Dragons and Pirates! What could possibly go better together? It's like peanut butter and chocolate right? Well, as scores of failed supplements have shown, it's actually a trickier mashup then you would think. While the spirit and style of the pirating in the age of sail is a natural and additive match to Dungeons and Dragons genre, there are a number of complications that can easily wreck or divert such a campaign. Unless you as a dungeon master are aware and proactive in your world building and scenario generation, you are likely to miss the mark of your expectations.

The purpose of this series of three posts is to share some of the learning from running such a campaign (now entering it's second year of continuous play) and provide a basic storytelling framework and toolkit for navigating the choices and trade offs presented.

First I will decompose what a pirate adventure IS into its core themes, what kind of gaming style and campaign world best suits it, and why it's not a slam dunk to just bolt pirating onto a run of the mill D&D campaign

In the second post of the series I'll dig into solutions, both for the world building and game mechanics shortfalls identified.

In the third and final section I will present a sample, playable campaign setting that implements the solutions and avoids the pitfalls.

Worldbuilding - Consistency and why it matters

In order to Pirate you have to have a world to Pirate in. Your options are to either build it yourself, adopt an "official pirate setting" (spoiler they are all mostly pretty bad) or extend an existing non piratey fantasy setting like Forgotten Realms or Greyhawk or whatever Magic the Gathering Inspired trash WotC is peddling these days.

The first step in making that decision, is to figure out how much internal consistency do you need in your world? I use the word "consistency" as a general adjective for "how much do you need your fantasy world to have rules of operation that make sense?"

"Rules of operation" can be anything from physics making sense to economics to culture to warfare.

The amount of consistency needed depends a lot on the playstyle your group prefers. In the following section I'll lay some groundwork for different playstyles and then talk about where Pirate Adventures fit best.

Internal Consistency is a continuum

D&D can easily run a gamete from "virtually no consistency we just want to fireball some goblins man" to "I am like Tolkien and I have the grammar for the actual languages in my world worked out in a notebook including multiple dialectics of elvish"

The reality is any place on that continuum can work well and generate a fun game, but several things are important to consider

It's important players and DM be aligned on how much consistency there is.
Certain levels of consistency are required for certain campaign structures. We will talk more about this later in the article but the tl;dr is the more you want to run a sandbox style game with a lot of player agency the more you want consistency, and conversely the more you are happy with adventures that are more or less on rails, with limited player choices, the less you need.
Consistency takes work. The more consistency you include the more work on both the part of the player and the DM is required. Also a corollary, DM's are often more invested in this effort then players, since lets face it you are love with your world and they are in love with their characters.

Running on Rails

Examples: About 90% of dungeon and dragons adventures (and fantasy novels) have the following general flow.

Bad Thing / Person is happening Out There
Adventures must undertake a set of heroic quests to find/rescue/discover/assemble the McGuffin of Salvation.
Adventures then use the McGuffin in the Final Showdown to defeat the Bad Thing

This is what I call an adventure that is "on rails". While players may be presented with cosmetic choices, they are not presented with choices that are meaningful to the outcome of the story. The outcome is essentially pre determined and the story unfolds in a linear fashion. Unless they get killed of course. To TPK, or not is basically the only choice.

This kind of adventure is the simplest to create and run (which is probably why WotC keeps cranking them out over and over again). It's an excellent choice for a casual group because it has clearly defined expectations and requires limited time investment from the players. You can just show up and play it. Time requirements for the DM are also light, generally world building requirements are extremely limited, mostly around stats for dramatis persona and the superficial elements of locations. "The Big Bad Guy lives in a huge black fortress up north surrounded by lava and here are his stats"

The principle downside is that after you've gone through a dozen or so such adventures it becomes very predictable and a trifle boring. It also tends to limit role playing, players that are roleplayed well will want to go "off script" which basically means going off the rails, which the DM is unprepared for.

Branching Narratives

This is the next step up in sophistication, and probably the place where most longer term homebrew campaigns and the better packaged adventures and video games operate. The adventure is about 70% "on rails" but throughout the course, the PC's are presented with choices and challenges. Depending on what happens they will fork down a path that has different outcomes from other potential paths. Usually these forks are pre-ordained, but there is nothing stopping a DM from allowing them on the fly as well. This method is a good compromise, doesn't require a huge investment from the players or the DM (though significantly more then the rails example), allows greater latitude for roleplaying and is far less predictable then the rails example.

Example: Whisperleaf decides to keep his appointment with the Mages guild even though he knows he is a wanted man. He picks up that something is off when talking to the gate warden (successfully perception role) at the library, and thus doesn't go in and get captured. The "rescue Whisperleaf from the mages guild" fork has been avoided. However he choose to go straight home to the Inn where the party is staying. He and Marius both fail their perception roles and don't realize they are being followed. They fail again later in the day as the soldiers get into position to arrest them. The "attack on the inn" fork has been activated.

However it still has some downsides, the most important being that it still operates in the role of the Dungeon Master as the principle storyteller and the players as mostly actors in the story. It provides some opportunity for player agency, but that agency is still limited to what is essentially a multiple choice test of "which ending do you want to get".

Sandbox Games and Player Driven Stories

To me, this is the pinnacle of TTRPG's and what really set them apart from books, video games and all the other competitors. The goal of a sandbox is to provide a group of players with an environment in which they can collaboratively tell their own story. The DM cedes his role of "Principle Storyteller" and instead facilitates the player created plotlines by presenting seeds to potential stories and representing the simulation of the rest of the world, the world-engine they are interacting with in and the various entities in that world.

The DM runs the world and the players figure out what they want to do and attempt to poke the simulation in various ways in order to get various things to happen.

This doesn't mean the DM doesn't have stories in their head that they are playing out. Things are happening in that world after all, there are other actors with other agendas in addition to the players, and those agendas will play off against eachother in various ways, even with no PC involvement. What it does mean is the DM has no firm plan for what the players will be doing or what the eventual outcome might be or even what kind of game this is going to be.

This type of story requires the highest level of engagement from the PC's and the DM, and also requires a lot of upfront world building work on the DM's side. It helps to have an experienced group of players, that are comfortable with the expectation that they drive the story rather then are driven. And it's a lot of work for the DM. Since you are essentially modeling an entire world in your head, with all the principle actors and events, the world building needs to be extensive.

However the principle advantage is that stories created this way tend to be far richer, much less predictable and can drive a far higher level of player engagement and emotional involvement.

At this point I am sure the reader will notice that the dividing line between "Branching narratives" and "Sandboxes" is far from absolute. Sandboxes can contain branching narrative storylines within them. Play Sessions can easily flip back and forth between more and less structure. A common occurrence for instance is for the players inside the sandbox to agree on a certain course of action, and set a goal for the story which then become more structured until that goal is either achieved or not.

Example: One of the things that is occurring in the background is the current country the players are living in is involved in a brutal civil war. The PC's are free to ignore this entirely if they choose, there are plenty of other things to do. But one of the PC's has chosen a background with a vested interest in supporting one side vs the other and manages to convince the party to intervene in some way. After some research, they brainstorm that the best way for a small group to have an impact on a large war is through a series of selective assassinations of key military and political leaders on the other side. Now the story becomes more of a branching style narrative, as the party selects their targets and moves toward execution of their plan. The DM says "huh I guess we are assassins' now" and plans accordingly. In an alternate timeline maybe the PC's decide that all those dead soldiers could be a huge asset and become necromancers attempting to keep the war going...

Which brings us back to our point about consistency in world building. That third type of sandbox story ONLY works if the world engine that the GM is running operates on internally consistent rules. The first two styles of play can operate primarily on Dungeon Master fiat, the DM can state what is happening, state the choices and their outcomes, the players at most have to choose a fork.

However once the DM cedes the principle narration role, the players need a way to plot and plan how their actions are likely to effect the simulation they are living in. The more they are able to understand how that simulation works, the more their plans will be successful. The more effort they invest in trying to understand how that simulation works, the more they will spot inconsistencies or exploits in the world-engine, and the more the DM will have to intervene vi fiat that "that won't work because" or alternatively the more the world-engine will get disrupted by the exploits.

Example: A DM designs a world where trade makes copious use of lighter then air airships, with the aspirations of cool steampunk style broadside actions between them. One of the players points out that battle between such airships would quickly devolve to attempt to puncture the gas bag of the enemy and hey, he knows fireball and is a sorcerer with the ability to massively increase the range of his spells. He is essentially unbeatable in airship combat and don't need no stinking cannon. The DM doesn't like this outcome so he invents a magical material that airship gasbags are made of that makes them impervious to fire. The party's fighter wraps himself in that material and suggests the other party members do the same. One player asks how the ship can even turn given it has no propulsion or keel resistance. The DM buries his head in his hands as his dream of pirate airships collapses under the assault of rationale thought and necessary consequences..

So what is the real problem here? Not the party following the simulation rules to their logical conclusion. The problem is the DM inventing an outcome he wanted (magical airships broadsiding each other) clumsily explaining that outcome by bolting on a set of rules (airships, broadsides, magical fire retardant cloth) that aren't internally consistent and frankly don't make sense in the broader context. In the event that a civilization had access to the underlying ability to create such things, they probably would not end up with pirate style airships. Pirate style doesn't fit.

Note this can be an issue even with rails style campaigns, a party suddenly sniffing out an exploit and going off the rails (why can't the magic eagles just fly us to Mordor) is always a risk. But it becomes much worse the more agency the players expect and become use to.

Which finally gets us to our conclusion, which is if you

Want a campaign with a pirate style
Want to include D&D classes and powers with all those ramifications
You probably have a problem

For one thing ships are made of wood and one of the principle ways they were destroyed was via fire. If you work around this by introducing ways that ships don't actually burn when hit by a fireball you need to do so carefully or now you have two problems.

And that's just one place where things go off the rails there are many. And this is one of the main reason why D&D pirate supplements fail.

Now it could be that at this point you have decided "my players are just not that sophisticated and this isn't going to be a problem and if it is I will DM fiat my way out it". And honestly that is fine, just be aware you are paying a price for that and the price it that in my opinion you will block access to the most fun and rewarding style of table top gaming.

But fear not, me hearties, there are better solutions available. The key is to make Pirating an EMERGENT property of the world (arises naturally) not a clumsily bolted on one, and low and behold we have a pretty good example from the real world to work with there...

Sandbox Games and Pirating

Connecting it all back to the main theme of this post, Pirate Adventures are uniquely and amazingly conducive to sandbox play styles. You have a ship that can sail a wide sea. You can go anywhere. You can do anything. The main impediment however is do pirates even make sense in the world you are playing in? As we dig in more to what make a pirate adventure a pirate adventure, this impediment becomes even more obvious.

The standard issue D&D fantasy world just doesn’t lend itself well to pirating on the high seas.

The fundamental qualities of a pirate adventure

So the next step in our world building adventures is "what does Pirating mean anyway?" What are the emergent properties of our world building that we want to see, that define success? And what kind of consistency do we need in order to get that thing in an emergent way?

Pirating has pirates

Kind of goes without saying but you need pirates. More specifically a pirate crew and a pirate captain who are free to do piracy. This means we need a world where

Piracy can be a sustainable thing that isn't instantly squashed by some government, god, or all powerful magical entity
The freedom of the pirate captain and crew must be maintained, i.e. they can't be swallowed up in some big criminal enterprise, or become so successful they become rulers or kings
Piracy that is too successful extincts its prey. Plus that's boring. So there must be obstacles to piracy.

This requires a balancing of forces, the pirates must accrue and maintain enough power and agency to survive, but not too much to become dominant.

Pirating has pirate ships

The Ship, along with the Captain and The Crew are the three principle characters of a pirate narrative. The ship must

Exist and take part in most of the narrative.
Be maintainable over time by only the crew (and possibly the occasional sojourn in a pirate port)
Be combat effective
Be fast enough to catch prey.
Sail on a Sea

Pirate ships must be properly piraty (this is more of an art call then a narrative call, but you know a pirate ship when you see it, and it's not an oil tanker or a jet fighter). They should generally have a crew in the dozens or even hundreds but not thousands or millions.

Pirating takes place on the Sea

In pirate stories the sea itself often plays the role of a major antagonist. And sometimes an ally. It doesn't necessarily need to be made of water but it needs to be

Large (travel over it should take significant time)
Dangerous, in and of itself (not just based on creatures and npc's you encounter)
Unpredictable (tides, currents, winds, storms)
Beautiful
Hard but not impossible to locate a ship in
Heavily used for commerce
Unexplored (at least partially)
Diverse, the gateway to exotic locales

Ships fight eachother with things that go "boom"

Some kind of cannon doing something like a broadside is essential to the genre. It needs to be loud and explodey
Ships without loud explodey cannon, we have a name for them and it's 'troop transport' not "pirate ship"
Ships do not die because they run out of hitpoints. They die because they are shot to pieces by something loud and explodey or because they catch fire and explode. They are not monsters but buildings that happen to float.
Boarding actions also need to be a thing, since the goal of a pirate is generally to capture his target not destroy it.

Pirates need to be morally ambiguous anti-heroes

Generally people that kill other people and take their stuff are not a fun persona for most people to play. We call those people "murderers" not "heroes". Also, buried deeply in the pirate genre is the idea that pirates are often not bad, or at least not entirely bad. This was actually surprisingly true for at least the first generation of pirates (16-17th century Caribbean) so you need something to set pirates apart from just "common thieves and murderers on boats".

A somewhat morally sound reason why they are pirates
A code by which they operate
A Pirate Society in which they exist, a brotherhood of pirates that govern how they interact with eachother

Pirates mean Freedom

The final point that defines the genre is pirates don't work for anyone but themselves and are governed by nothing but their own will. As soon as you make them part of some hierarchy and start giving them orders that they must obey, they are no longer pirates.

It also helps to have counter force that the pirates are rebelling against. A society or culture that represents anti-freedom in some way, that can become a contrast and foil.

The generic D&D fantasy world and why it doesn't work well for pirates

Most D&D settings are based on the high medieval period with dashes of Middle Earth. However despite the existence of plate mail and clever dwarven smiths they mysteriously don't have cannon or firearms. In addition to not making much sense in and of themselves, there are a number of reasons why such a time period has difficulty delivering the our fundamental pirate traits.

Guns, Cannon and pirate ships oh my

Most D&D settings don't have guns and cannons. Cannons especially are historically a BIG DEAL. They completely changed the way warfare and fortifications worked and basically killed feudalism. Gunpowder sidearms had almost as much influence, they obsoleted armor for instance. Just blanket adding guns and cannons onto a fantasy world is a recipe for disaster and will wreck what internal consistency most of them have (which honestly ain't much to begin with). Most notably, once you have cannon forget about castles. "Boom" go the cannons, "crash" go your curtain walls. They'd do a number on most large monsters too. Hello Mr Dragon let me introduce you to a little thing I call "massed musket fire".

Similarly tacking on Age of Sail Tall Ships into a medieval setting will also wreck things in more subtle ways. Economics, trade, warfare, communications all becomes sea based very quickly. Floating cannon platforms are powerful. Rapid changes to the balance of power would result. There is a reason why the Dutch of all people became a superpower during that timeframe in the real world.

Finally trade and ocean travel just isn't the focus of most D&D settings, they typically treat the oceans as big blue blobs that you travel over to get to the elf homelands in the west. Where ships are even mentioned, its mostly a way to get from one place to another place, but not a focus in and of itself. Except when a sea monsters attacks you on the way to the elf homelands in the west and you, I don't know, beat it up with swords or something.

So you don't gain much from using an established setting anyway and you actually create a ton of work for yourself even trying.

Attempting to fast forward the technology of a standard fantasy world (like Forgotten Realms or Greyhawk) to allow the pirate traits we need to be emergent rather then just bolt-on, well you are essentially going to have to rewrite the entire thing so why bother?

However it IS perfectly possible to use a standard D&D fantasy settings as a "jumping off" place for a pirate campaign that happens somewhere else. Some place far away where the world-engine is designed from the ground up to be conducive to the kind of adventure you are trying to run, that's entirely feasible.

Almost all fantasy worlds contain The Sea in some way or shape or form. Having the players travel far over the sea to get to the Pirate Lands allows you to introduce the things you want to introduce in a controlled setting without disrupting your fantasy land dynamics.

D&D Rules and where they don't work for Pirating

Levels are not your friend

The three primary characters in a pirate saga are the Ship, The Captain, and the Crew. Pirate crews need to be larger than the party and contain NPC's in order to make lots of cannon go boom. Plus you need the flavor of a pirate gang, it can't be just you and the npc cleric and the grump tiefling warlock. Enemy pirate ships need to be a threat. Player characters need to be powerful enough to overcome small groups of enemy crew but not powerful enough to be able to slaughter an entire ship worth of crew single handedly.

This gives you as a storyteller two choices.

Start with player characters of relatively low level
Make all the bad pirates high level

My personally experience here is that the sweet spot for a pirate campaign is generally PC's starting at around level 5 and capping out at around level 11. This allows you to run relatively veteran Crews at a range of 2-5 (which gives a nice set of class abilities while still constraining power levels and allowing the PC's to outshine them noticeable). It avoids most of the really powerful gimmicky unbalanced spells early while still letting you wow the enemy with a fireball or two.

Magic is not your friend

Ships. Are made of wood. And cloth. And rope.. All that stuff burns. Magic in D&D makes lots of fire relatively easily.

Ships sail on the water and have trouble in storms. Magic in D&D can whip up some storms and lightning relatively easily.

It's even easier for magic to create food and water pretty much endlessly, which has the effect of giving sailing ships essentially unlimited range.

Even relatively lowly 3rd level spells will quickly dominate ship on ship combat. Higher level spellcasters will eat ships of the line for breakfast and ask for seconds.

Unless you want your ship combat to derail quickly into "magical platforms for spellcasters to lob fireballs at eachother" you, as a DM need to do something about this.

Making anyone higher the lvl 3-5 uncommon helps here, but what helps even more is making spellcasters very uncommon. Especially high level ones.

In general, pirating campaigns work a LOT better as low magic rather then high magic campaigns. Letting the PCs have magic is fine, but I highly recommend civilized spellcasters < 3rd level being extremely rare.

Which brings us to...

Ship combat does not translate well into Dungeons and Dragons

Tall Ships in the Age of Sail, evenly relatively lowly frigates, often had scores of crew. If the ship was a warship it would have hundreds and would literally be packed to the gills with fighting men. This went double for pirate ships Two reasons for this

Cannon take a lot of people to operate effectively
Boarding actions meant having more crew meant winning the boarding action

Dungeons and Dragons does not work well in combats with even twenty people on each side. You can easily have 200 on each ship.

In addition the hitpoint system that a lot of expansions extend to cover ships is abysmal at delivering the feel of two tall ships slugging it out on the seas. It has no concept of incremental damage, and is generally a "you are fine until you are dead" combat system.

Various supplements try to work around this in various ways, but the reality is the D&D system is garbage for this so don't use it for ship combat at all.

There happens to be a much better system that is easy to bolt on to D&D that we will talk about in the next post.

Conclusion

So we've presented what success looks like in a pirate campaign and some of the obstacles that we need to overcome to do a good job of it.

In the next post we will

Present a template for world building that actually works and fosters the emergent properties we want (spoiler, start with the real world, mix well and add magic)
Present some counters to limit magic in a way that doesn't destroy a campaign
Talk about using alternate systems to D&D for ship combat.

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D&D and Pirating - Part 1 - What is a Pirate Adventure?