Adventuring as Pirates: Rogues

Character creation is one of my favorite things, which might be why I prefer to DM. By managing the game I get to create hundreds of characters – some fully fleshed out re-occurring NPCs and others are simple one shot monsters. For a friend’s campaign I needed to create a PC, something which I haven’t done often in the past two years (this is my second playable PC). While I do make a lot of NPCs with the rules for standard players, as it helps me think about how the more complex enemies and allies behave.

For my character I wanted to do a few things a bit different. As most of the players are new to 5th edition and some to D&D at all I wanted to be a support caster. I decided on a Cleric. I always like Krynn’s Minotaurs so went with that. Wanting to justify my greater player knowledge I thought about going with the Knowledge Domain. But where does a ocean going minotaur fit into the Forgotten Realms as a Cleric of Knowledge. My answer was as a pirate ship’s quartermaster. As a follower of Deneir Golrian Hershmakil the Quartermaster of Estadia keeps precise records, logs and maps of the Estadia’s forays at sea and land.

Pirate Ship by Carlo Mirante

Pirate Ship by Carlo Mirante from

And then I thought, “what role would every archetype have on a pirate vessel?” This launched a ton of thoughts about a piracy campaign, which I have no time to run, but it lets me use creative processes that the current Everflow campaign does not.

Rules of the ‘Pirate All Classes’ game

  • Use third level
  • At least 50% of the concepts must have Vehicles (Water), Athletics (for swimming, climbing jumping) or Acrobatics (for working in the rigging)
  • Some may be Privateers rather than pirates, but the goal is to mostly represent those that were unsanctioned
  • Assume no gunpowder
  • Recognize that no ship will have every concept created so more than 1 can be a captain
  • Recognize that pirate life is as much about life in port as at sea
  • Don’t use stat groups, instead show the interaction between class, background and ship role.

Starting with Rogues as they are the most pirate-like by nature. The Player’s Handbook and Sword Coast Adventurers’ Guide includes the following archetypes – Thief, Assassin, Arcane Trickster, Mastermind and Swashbuckler.

Thief of the High Seas

On the ship you are a mild rigger working the sails, scrambling up and down the ropes faster than anyone else. Sure, when your boat needs to board another you are ready, swinging across either sneaking into quarters or taking out lookouts, but it’s in port where you make the real difference. Stealthily listening in on merchant captains, stealing keys or maps, or breaking into that jail to let your people free, you are the eyes, ears and rogue of the crew.

Take expertise in two of Stealth, Thieves Tools and Acrobatics. Also have Sleight of Hand, Deception or Athletics (for swimming) as well. Pick a background like Urchin or Sailor to try and get another way to get one of the key skills so you can make certain to have Perception. It’s great when you are 50+ feet above the ship and can see everything that happens, probably with Advantage.

High attributes should be in Dex and either Wisdom or Charisma depending on how much fencing (the selling kind) you do.


Most of the crew considers you the cook, and you do that. But it seems when the ship is at battle you disappear. What you are really doing is seeking out the highest value target on the opposing ship as you swim over to it and get the drop from an unexpected angle. In port you slip into parties to pick up information from the authorities, maybe slipping a little poison into a glass or two.

Take expertise in Athletics and Stealth. It’s also handy to have Insight, Persuasion, Deception and Sleight of Hand. Any background is suitable, try not to be a sailor or pirate. You don’t have sea legs. Noble and Guild Artisan (Cook) can create great cover stories for yourself. Get Gourmand as soon as you can.

Charisma is an important stat with your role on land. A high Dex and Strength can both be useful too, especially if you choose to swim a lot.

Arcane Trickster

Being at sea for days and days and days can be boring. You know what brightens a day? Illusions and parlor tricks. That’s why most of the crew has you around, but the captain and quartermaster know better. They have you around because it’s a lot easier to get a good deal selling the ship’s “merchandise” through Enchantment or Illusion. Swabbie by day isn’t a fun gig, but your Mage Hand helps make the work go quickly, just not too quickly, then they would give you more work to do.

Expertise in Deception, Insight or Persuasion are key. Sleight of Hand can be useful as well. Take the Sailor (Pirate) background so that you know Vehicles (Water).

Charisma will be your key stat, but as for all Rogues one of your top two should be Dexterity.


The crew handed over control of the ship to you a few ports ago. They understand that you understand and know command. The galleon practically leaps at your command. You can find wind where others are helpless. In port you can infiltrate parties, or go as yourself. You have a reputation. When your black flies, people tremble. Other sailors respect you for you have put in the work. They also know that when you are around you Help them.

Expertise in Intimidation, Insight or Deception are key. You are a ship’s Urchin, use the Urchin background, but modify it a bit. Rather than the Disguise Kit take Vehicles (Water) and replace Sleight of Hand with Performance. You grew up on this ship and now it is yours.

Charisma and Wisdom should be your two highest attributes. You do not get in fights, you prevent them or win them so quickly your opponent does not get to attack.


As the Master-At-Arms you lead the boarding party. With a blade in each hand you dart in and out of the battle. When not overwhelming those foolish enough to stand up to you are “training” the crew in the art of swordplay. Most of this involves you embarrassing them just enough to try harder. Most of the crew do not like you, but they respect you. You’ll never be a captain, but you will be feared and respected.

Expertise in Acrobatics and Athletics are vital for the fancy moves you do as you tumble from ship-to-ship or swing through the nets and ropes. Intimidation can be handy, and the little flourish with your blades show that you are tricky with your hands too (Sleight of Hand). Once a fancy Courtier (background from SCAG) you are now on a pirate vessel, raising funds so that someday you will have courtiers.

Dexterity and Charisma should be your highest attributes.

Above you have the start of a crew. A captain, a cook, a swabbie, a rigger and the master-at-arms may even be enough for a small sloop.

5 thoughts on “Adventuring as Pirates: Rogues

  1. Pingback: Adventuring as Pirates: Bards | Full Moon Storytelling

  2. Pingback: So, you got into ShanyTok, now what | Full Moon Storytelling

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