Tips And Tricks For Running Pirates In DND

Pirates have always been a thrilling addition to Dungeons & Dragons campaigns, offering a blend of high-seas adventure, swashbuckling action, and moral ambiguity. Whether you’re crafting a tale of treasure hunts, naval battles, or political intrigue on the open ocean, pirates can add dynamic challenges and rich role-playing opportunities to any setting.

Running a pirate-themed campaign requires balancing nautical mechanics with compelling storytelling, from managing ship-to-ship combat to developing memorable pirate NPCs. Whether your players are fearsome buccaneers or brave heroes chasing down scallywags, here’s how to bring pirate adventures to life in your D&D game.

7

Make The Pirates Particularly Charming

It Is In Their Nature

All pirate variants in the 2024 Monster Manual have the ability to charm their opponents for a turn, and in combat, that mostly translates to not being able to harm the pirate directly. While that can make for a functionally diverse fight, it can be hard to understand for players why they are charmed if you don’t present the pirate correctly.

Consider removing the ability for certain basic pirates if players are facing too many of them, so the ones that can charm are even more special.

The idea is that the pirate’s opponents are too awestruck to even think about harming the pirate, so that aspect of the pirate should be present in every single interaction. Each one of their attacks should have a flourish, and even in conversation they should be the most alluring person in the room.

6

Have Pirates Explore The Multiverse

The Astral Sea Is A Sea After All

Pirates as NPCs can appear at any moment in a campaign, being friends, foes, or simply a means to an end. Since ships in Dungeons & Dragons can traverse the seas, air and even the barriers between universes, a friendly pirate crew can be how a party gets from one place to another.

In essence, if you want to include pirates in your campaign, don’t let that limit you; they can appear anywhere. This helps to use the highest CR pirate, the Pirate Admiral, since with a CR of 12 the party might be outside the Material Plane already.

5

Get Your Pistol Rules In Order

Players Will Want A Multi-Attack Pistol

Both the Pirate Captain and the Pirate Admiral carry a pistol, and they are able to deal multiple attacks per turn with it. This isn’t normally possible with pistols, something certain rule-savvy players might pick up on and either ask you about it or wish to loot the pistol off of the pirate’s corpse.

Now, just because a creature can do something doesn’t mean a player can, but that might not suffice to appease everyone at the table. The most elegant solution, assuming you allow feats from all books, is to say that the pirates have the Gunner feat from Tasha’s Cauldron of Everything, letting them ignore the loading property of firearms.

4

Make Pirates Outlaws, Not Evil

They Are Closer To Chaotic Neutral

The pirates from your campaign can be anything you want them to be: good-aligned freedom fighters, evil treasure hunters, whatever you might need. But in general terms, they aren’t either of those things. They just want to live freely outside of society’s norms.

This can make them more complex than simple enemies at the end of a dungeon, with an outlook that can be in line with how the players see the world. After all, most parties want to explore the world and see what treasure they can find at the end of the road.

3

Have Greed Be A Pirate’s Main Flaw

This Works When They Are Allies Or Foes

Pirates like to plunder, that much is just in their nature. This can make them a great source of knowledge regarding ancient treasures, but it can also make them careless when it comes to acquiring them, throwing caution to the wind and landing head first in innumerable traps.

Knowing this about pirates can help you define how they approach most situations, no matter their attitude towards the party. It can even help the players make plans against pirates, either outsmarting them with the promise of fake treasure or beating them in a race to get it.

2

Have Pirates Be Loyal To Their Crew

Mutinies Should Be An Event, Not The Norm

Pirates might seem selfish and greedy individuals, and while that is generally true, they are loyal to their crew and captain; otherwise, they would just be lonely mercenaries. This means that, even when successfully intimidating a pirate, they might still be reluctant to betray their captain.

The Pirate Admiral’s Rally ability is a perfect way to aid the players without meddling too much in combat, giving up to three target advantage in D20 tests for a turn.

This can also be a good way to have characters like the classic lawful-good paladin interact with pirates. If the party spares the life of a pirate, then down the road they might be unexpectedly aided by its captain, looking to settle a debt.

1

Give Pirates Allies Other Than Other Pirates

They Should Be Good At Making Allies

Pirates should be good at making contacts, but the nature of said contacts would depend on what sea they call home. Those traversing the watery expanse of the Material Plane might have uneasy alliances with a group of Sahuagin, while pirates of the Astral Sea might have trade routes that deal with the Githyanki.

Pirates can be of any humanoid species; try to make them more varied than just humans.

This will let you have more diverse encounters, since fans of pirate stories can struggle with only three pirate stat blocks. Still, as stated before, remember that pirates are only loyal to their crew, and won’t hesitate to backstab other allies for the sake of treasure or survival.