Pirate Roleplay Prompts

Twenty original pirate roleplay prompts: mutinies, treasure maps, naval hunters, sea legends and the strange freedom of a life with no flag. Each has a hook and a first message ready to paste. All ships, crews and islands here are invented.

Pirate stories are perfect for roleplay because a ship is a small world with big stakes: a crew that has to trust each other, a captain who might be overthrown, and an ocean that doesn't care who wins.

Set your sails

Decide a few things before the first message:

• Historical or fantastical? Real-world age of sail, or sea monsters and cursed gold?
• Your persona's role? Captain, new recruit, navigator, prisoner, naval officer, stowaway?
• What does the crew want? Treasure, revenge, freedom, survival, a pardon?

Joining the crew

1. The pressed recruit. You were knocked out in a tavern and woke up aboard a pirate ship, already signed onto the crew.

The quartermaster drops a mop at my feet. "Your mark's on the articles. Welcome aboard. Deck's filthy."

2. The navigator for hire. A pirate captain needs a navigator who can read an ancient star chart. You're the only one in port who can.

She unrolls the chart on the tavern table. "Read this, and you're crew. Lie to me, and you're ballast."

3. The cabin boy who isn't. The ship's quiet cabin boy has just been revealed as the runaway daughter of the admiral hunting you.

I stand between her and the furious crew. "Before anyone does anything stupid, she's the reason we've avoided the fleet for three weeks."

4. The stowaway cook. You stowed away on a pirate ship to escape your old life. You've been discovered in the galley, cooking.

The captain tastes the stew, then looks at me for a long moment. "…You can stay. But you're cooking every night."

Treasure

5. The map in pieces. A legendary treasure map was torn in four. You have one piece. So does a rival captain.

We lay our pieces side by side on the barrel. "Partnership," I say. "Until we find it." "And then?" "And then we see who's faster."

6. The cursed gold. The crew finally found the treasure. Since then, every man who touched it has started hearing whispers.

The bosun grabs my arm. "You heard it too, didn't you? Last night. Saying your name."

7. The island that moves. The treasure island on your map was charted in the same place three times, by three captains. It's never been there twice.

I lower the spyglass. "It's gone. Again. Captain, I think the island's moving."

8. The treasure that's a person. You've reached the X on the map. Instead of a chest, there's someone chained in a cave who's been waiting a very long time.

The prisoner looks up. "Finally. You're late. By about forty years."

Mutiny and loyalty

9. The mutiny. The crew is planning a mutiny against the captain tonight. They want you to join. The captain saved your life.

The first mate presses a pistol into my hand under the table. "Midnight. Are you in?"

10. The captain's secret. You've discovered the captain has been secretly paying off a naval officer to let the ship pass.

I close the captain's cabin door behind me and set the letter on his desk. "How long?"

11. The new captain. The captain is dead and the crew has voted. To everyone's shock, including yours, they chose you.

Forty faces stare at me from the deck. "Right. First order: nobody panic. Second order: does anyone actually know how to sail?"

12. The marooned. You were marooned on an island by your own crew. Today, a ship appears on the horizon, flying your old flag.

I stand on the beach as the longboat rows ashore. The first mate who marooned me is at the oars. "We need you back."

The navy and the law

13. The officer and the pirate. You're a naval officer who has just captured the most wanted pirate on the seas. They're surprisingly good company.

The pirate leans back in the brig, utterly relaxed. "You know they'll hang me in port. So we've got eleven days to become friends."

14. The pardon. The crown is offering pirates a full pardon, for one last job.

The governor slides the pardon across the desk. "Sign this, and you're free. All you have to do is betray your former captain."

15. The double agent. You've been sent undercover aboard a pirate ship by the navy. You're starting to like the crew more than your orders.

The captain hands me a share of the take. "You've earned it. Never seen a landlubber learn the ropes so fast." I take it, and feel sick.

16. The blockade. A naval blockade has trapped your ship in harbour. You have one night to slip out.

I look at the line of warships across the harbour mouth. "Kill the lanterns. We go at moonset. Nobody breathes loud."

Sea legends

17. The siren's bargain. A siren has stopped your ship in a dead calm. She'll let you go, for a story she's never heard.

She rests her arms on the rail, water dripping. "Every sailor tells me the same stories. Tell me something new, and I'll give you wind."

18. The ghost ship. A ship with tattered sails and no crew has drifted alongside yours. Its log ends with your ship's name.

I hold the log up to the lantern. "'We sighted the Ember Gull at dawn.' That's us. That's today."

19. The sea witch. The ship's been cursed with endless storms. Only the sea witch can lift it, and she wants something specific from you.

She stirs a bowl of black water. "I don't want gold, sailor. I want your name. Your real one."

20. The edge of the map. Your captain wants to sail past the edge of every known chart. The crew thinks it's madness.

The captain taps the blank part of the map. "Everyone says there's nothing there. Aren't you curious who decided that?"

Making pirate stories work

• The crew is a character. Name a few: the grumpy cook, the superstitious lookout, the quartermaster who runs everything.
• Freedom has a cost. Pirates are free, and hunted.
• Use the sea. Weather, calm, storms and tides are plot devices.

A crew becomes found family almost by default. For a navy-and-pirate romance, try enemies to lovers. For more adventure on the wrong side of the law, see the heist prompts and Wild West prompts.

Adventurers on Minkplay

Captain Roger of the Voidfarer is essentially a pirate captain among the stars. Smuggler, starship commander, and a man who recruited a stowaway instead of throwing them out. Axel the junk raider scavenges wrecks in the asteroid belt. Both are listed below.