Two years ago, I organized with a friend of mine a roleplaying game for my birthday with 17 people set in 1929 New York, where we played different members of an Italian crime family.
This year, for Kaonashi’s birthday, I proposed to plan another one again. We settled very fast on the Pirate theme, which we both like and has a lot of potential, and I sent her on her way to come up with the guest list so I could start planning.
On the 20th of December 2025, after a few weeks of preparation, we played an 18-person costumed roleplaying game where we had lots of fun!
This roleplaying game sits somewhere between a murder mystery, an escape game, and a traditional tabletop RPG. I’m playing a lot of traditional tabletop RPG (D&D, Witcher, BlackFlag, Cops, Warhammer fantasy…), sometimes as a player, and sometimes as a Dungeon Master. These games are usually for 4 to 5 players around a table, so this was a very different beast, but still, many of the tricks I learned DMing in regular games helped me prepare for this one!
In this post, I’ll focus on how I structured the scenario: factions, goals, puzzles, and the characters. In the next post, I’ll go into details about how I made every prop from the map used in a puzzle to the daggers and gold coins shared with the players. Finally, I’ll explain how we set up everything just before the game and how I started it, and give a good recap of what happened during the game, what worked, and what didn’t.
Factions - Organization help
As soon as I had a rough estimate of the number of players, I started working on the global setting.
For the time period, I picked around 1715 without really having to think too much, the golden age of piracy, which was perfect.
The first big decision was to pick what the players would be. I had multiple options:
- A single pirate crew on their ship
- Pirates from plenty of ships meeting up
- on an island to plan something
- in a random tavern on Nassau
- Two pirate crews
- on a third ship, they just captured
- looking for the same treasure
With the pirate theme, I knew I wanted to put some “Escape game” style elements in the game, clues to follow, puzzles, maps… And I thought that maybe having everyone be part of the same crew would allow me to reduce some of the initial suspicions/tensions the players could have with pirates from other crews, so I went with the first option.
I still needed to find some factions. In a huge roleplaying game like that, I didn’t want everyone to work together, I needed to create some potential conflicts as the game went on.
I started with two factions:
- The Loyalists - Trusting the Captain, and working with him
- The Mutineers - Unhappy sailors, maybe looking to replace the current leadership
The first draft of the plot then looked like this: The crew recently found a chest, but didn’t manage to open it, the Captain is locking himself in his cabin, while some people are getting annoyed that there is no payout yet. The Loyalists need to find a way to open the chest to appease the tempers, and the Mutineers are trying to recruit enough people to ask for a vote and replace the Captain.
But with 18 persons, even accounting for ~3-5 NPCs (Non Player Characters), that created big teams and a third smaller “outsider” faction often adds a lot of fun to the interactions, so I added:
- The Curseseekers - Somewhat unaligned, they believe the chest is cursed, they want to understand more about this treasure.
Now everything started to fall in place. I had my three factions with a big goal for each of them, I just needed to flesh them out.
The Loyalists would be the “balanced” faction, half puzzle / half social interactions. The Mutineers would be the more social faction. The Curseseekers would be the puzzle-focused faction.
Three factions need three leaders, so I enrolled three buddies of mine to each lead one of those. They would act as quest giver, introduce characters to each other, nudge players towards something if the game stalled, and overall help me run the game. I also recruited a fourth helper to have another neutral character for the players to interact with if they had any doubts, and to also man the bar during the game.
I had a treasure, a curse, and a mutiny to plan.
Players background
First, I assigned a character to each player. Since they were all part of the same crew, I listed a few jobs often found on a pirate ship, and then had fun with a few others. I ended up with this:
Myself as the Quarter-master, my four helpers as the Storekeeper, the Second, the Bosun, and the Cook.
Then for the players:
- The masters making sure the ship stays afloat: master carpenter, master caulker, master sailmaker
- Regular crew to man the ship: a chief gunner, a gun captain, a rigger, a cabin boy, a mate (who deserted from the French Royal Navy)
- Somewhat specialized crew: the pilot, the helmsman, the lookout, and the surgeon
- And what I called the guests: a survivor they found on the island with the chest, and a Captain from another ship who got marooned by his crew and was on board thanks to his friendship with the Captain
The goal was for everyone to have a unique job to allow them to distinguish themselves easily and to give them something a bit unique. I suggested a few nicknames for each position to go along with and told them to pick one or come up with another before the game.
It also allowed me to plan the initial affiliations to each faction and where some items would go. Then it was time for the quests.
The Loyalists
I started with the Loyalists. This seemed logical as it was going to be the faction with the most players at the start of the game, and figuring out what they had to do to open the chest would give me hooks for the two other factions.
I decided that the NPC leading them would be the Second. The right hand of the Captain, loyal and reliable.
The first idea I had was to make a puzzle with a map. I wanted the players to fold it in a certain way to reveal something, and they needed to be able to test their solutions themselves, so I figured a lock on the chest would be great, and the folded map could reveal the combination to open it.
So I needed to make a map and a page of instructions. This is where I came up with the “Treasure of the Black Thorn”:
The Black Thorn was a pirate Captain who terrorized a part of the seas. His legend says that he buried a fabulous treasure shortly before disappearing. The truth is somewhat different, he did bury a treasure, but it was because it was cursed. He spent a long time looking for it, but as soon as he obtained it, the curse hit him. He could not escape the storms that were following him, some of his men died of sickness or fell out in the sea, and some monsters even attacked his ship. He then made the decision to bury and lock the treasure so that the curse would not propagate to another crew. He didn’t just throw it into the bottom of the ocean because he was sure there was a way to lift the curse, and if some pirate was clever enough to find the treasure, he hoped they’d be smart enough to figure out the curse as well.
The map would be a custom map with fictional islands, ports, and names. The instructions would be on the last page of the logbook of the Black Thorn. For this faction, I wanted the puzzle to be on the simpler side, so I didn’t add a lot of steps.
There would be three notes hidden in the game location:
-
The first one would be a letter to the Captain of the ship, mentioning the treasure of the Black Thorn - It’s just lore, not useful to progress on the puzzle.
-
The second one would be a note from the Captain mentioning that he found the map and where he hid it. This would lead to the map that was in the possession of the Pilot.
-
The third one would be another note from the Captain mentioning that he found half a page from the Black Thorn logbook and where he hid it. This would lead to half of the instructions, which were hidden in the Surgeon’s notebook, and the Survivor had the other half and was instructed through his backstory to only recall it once he saw the other half.
I’ll go into details about how I made the props in the next post of this series.
For each of these steps, I’ve added a few possible hints that the NPCs could give if the players were stuck too long (a hint around the location of each hidden note or some insights into who to ask if they needed to find a specific item ).
During the end-of-game reunion, if they managed to open the chest, they’ll be able to reveal to everybody that the Captain was right to pursue this treasure and share the spoils with the rest of the crew.
Once I had the main goal, I also needed to add plenty of little side quests that the Second could use to slow the players if they progressed too fast on the puzzle, to give to some players who were not busy at the moment, or just to create some fun activities.
The side quests I had in mind were:
-
Send one player as a spy in the Mutineers faction.
-
Send players to recruit more players if the two other factions are getting too big.
-
Send players to play mini-games with other NPCs to try to “lighten the mood” of the crew. I’ll talk about the mini-games in a later section.
-
Send players to ask the Storekeeper NPC for another rum ration and help him give some to everybody, tell them it’s from the Captain.
-
Send players to watch over the weapons stash to make sure other factions are not arming themselves (This one could create some fun interactions with the Mutineers).
For the side quests, I kept it really simple, giving a lot of room for improvisation to the NPC leading the faction. Most of them never got played, the idea was just to give some tools to the NPCs to help change the tempo of the game.
The Mutineers
I then worked on the Mutineers, this faction was simpler to prepare because a lot of their objectives were social ones, so it wouldn’t need tons of written props (I did 3D print a few things for them…). Their NPC leader, the bosun, wants to trigger a vote to replace the Captain and be elected in its place.
But before doing that, he needs to prepare himself. His faction only starts with a few players, not enough to win a vote.
-
The first step would be to get gold. Enough gold to buy the loyalty of some other pirates. His players will need to play a lot of the mini-games onboard to get the funds necessary.
- A pair of crooked dice would also be hidden onboard to help them win at the dice game.
-
Then, they will be able to start recruiting. They’ll need to convince people, with gold, promise of promotions, or whatever else they can come up with, that their interest will be better served by the bosun.
- Once they find someone, they’ll have to bring them to the bosun so that the arrangement can be finalized.
-
Finally, to show that they are serious, they should arm themselves with a few weapons from the weapon stash. Unfortunately, it’s locked, and the key is in the hand of the Storekeeper NPC.
- Once they manage to get their hands on the key (through some social interactions with the Storekeeper), they’ll still need to get the weapons without getting caught (which can be harder if the Loyalist sent a few people to check on the weapons).
During the end-of-game reunion, the bosun will ask for a vote, and if they managed to accomplish their quests, maybe the Captain will be overthrown. It turned out to be very difficult to play. I made a few mistakes when setting up the game that I’ll speak about more in the retex post of the series, but I think it might have been too broad a goal.
In the same vein as the Loyalists, I cooked up quite a few side quests for them:
-
Send a spy into the Loyalist faction.
-
Buy a round of rum for everybody from the bosun.
-
Send players to try to create false rumors about the Captain.
-
Send players to create some tensions between the Curseseekers and the Loyalists to hopefully get the Curseseekers votes.
-
Send players to slow down the Loyalists if they make too much progress by stealing one of their items from the hands of the Second.
The Curseseekers
Finally, I only had the Curseseekers left, the old Cook would be the NPC in charge of them, a crazy pirate spending all his time speaking of nonsensical tales and legends… or is he?
The old Cook had heard of the Black Thorn, but he’s also persuaded that the loot is cursed and not just up for grabs. Nobody takes him seriously anymore, but maybe if he can convince a few people, they can understand how to lift the curse.
Starting with only a few players as well, this faction is the more puzzle-focused one. They still have to interact with other players to trade information, gold, or props, but they’ll need to spend some serious time working on their puzzle.
I knew I wanted a puzzle that would use a map of the stars because that reminded me of a mission in Sea of Thieves that was kinda fun, so I started working on that one.
-
Using the map of the seas (the same as the one the Loyalists need), by tracing an itinerary on it, a constellation would appear
-
Another player unrelated to this faction would have a document with some constellations on it, and by matching what they traced, they could deduce which constellation was the correct one.
I also wanted to incorporate a non-trivial logic puzzle, so I looked into Zebra Puzzle and, after solving a few, made my own adapted for my setting.
- A set of instructions would explain the zebra puzzle, and by solving it, the players could associate different elements: an animal, a precious stone, a location, and a time of the day. The solution would be the stone of the animal they found in the constellation.
I now had two elements, a constellation, and a stone, and with the constellation already a drawing on tracing paper, I decided to also create drawings of the stones on another sheet that another player would have. Using both at the same time and placing them on another prop with some text, the dots used in the drawings would each point to a word forming a phrase indicating where to go to lift the curse.
To know where to place them on the legend, I added a final prop that was a dagger with two icons drawn on it. The icons were also present in the text to indicate where to place the paper.
So for this faction, I needed
- A set of constellations on tracing paper.
- A set of precious stones on tracing paper.
- One page of the Black Thorn logbook with instructions on how to find the correct constellations.
- One page of the Black Thorn logbook with instructions on how to solve the Zebra puzzle.
- A legend containing a secret code once the tracing paper was placed on it.
- A dagger with icons.
Reusing the map from the Loyalist saved me one prop and would create more interactions between factions. This was the hardest faction to create the props for, as you will see in the following post.
During the end-of-game reunion, if they managed to find the way to lift the curse, the Cook would be able to intervene and speak about the legend.
I didn’t create any side quests for this faction, but talked with the NPC leading them at the start of the game to brief him on the timing needed so that he could slow down his players with some nonsense if needed (it seems that the puzzles were hard enough, as this was not necessary during our game).
Write the initial lore that will be transmitted to the players
Now that I had all the quests and drafts of every prop, I had a very good idea of what the story was. So I wrote the introduction that would be given to everybody at the start of the game:
December 1715, off the American coast, aboard the “Crimson Fox”.
The atmosphere aboard this pirate vessel is heavy. The crew of about twenty members is noticeably tense. It has now been almost six months since you began following the trail of the treasure of the “Black Thorn,” and last week, you finally got your hands on what may contain that treasure.
You had just set foot on the island where the treasure was supposed to be located when a ship of the French Royal Navy appeared on the horizon, heading straight toward you. Your gunner managed to dismast them with a pair of chained cannonballs, buying you precious time to find a chest, a dagger, and a man abandoned on the island, and to make your escape without lingering.
Since then, the small chest you recovered appears to be completely sealed. It is made of a material you do not recognize, and you have been unable to force it open. Your Captain no longer leaves his cabin, and some discontented voices are beginning to be heard…
I had a first draft of this introduction written before the quests, but the final version was written only once I knew what everyone’s goals were.
Mini-games and bar
I now needed to add a few things for the players to do during the game, some downtime activities between two quests, a way to just relax and have fun, maybe spend or earn some gold coins.
So I decided that the 4 NPCs helping me would each also be responsible for a mini-game they could play during the game.
The games were Liar’s Dice, BlackRobert (Blackjack), Pitching pennies and Osselets / Knucklebones. Each NPC had tons of spare coins to inject into the game through those little activities.
Players could also buy rounds for everyone or special drinks for themselves by speaking with the storekeeper.
Finishing the characters
The last step was to finish each player character by giving them a short backstory, an item, and a personal quest that they would have to do during the game.
I started by dispatching the quest items:
-
The map -> hidden with a bunch of other maps (that I printed) and given to the pilot.
-
Half of a page of the Black Thorn logbook on how to open the chest -> hidden in the surgeon’s notes.
-
The other half of a page of the Black Thorn logbook on how to open the chest -> in the survivor’s pocket, with instructions to not remember it until he saw another page half destroyed (amnesia background).
-
The constellations map -> given to the lookout.
-
The precious stones drawing -> given to the master caulker.
-
The legend of the curse -> given to the cabin boy, who stole it from the cook.
-
The page of the Black Thorn logbook to find the constellation -> given to the mate from the Royal Navy.
-
The page of the Black Thorn logbook to find the precious stone -> given to the gun captain (was supposed to be given to the other Captain at first, but had to make some changes).
I then worked on the quests and made sure every player had some item for the game that would create some interaction with other players.
Chief Gunner - Loyalist
The Chief Gunner’s quest, which was the birthday girl, was to get everybody else to sign and write something praising her amazing skills on a piece of paper. It was a simple way to help her interact with as many people as possible during the game and get a fun keepsake (it worked very well!).
Pilot - Loyalist && Master caulker - Curseseeker
The pilot and the master caulker had a shared personal quest. They had to find 5 rings that they had lost on board. I gave each of them one ring so they could recognize the others. I then hid 3 rings in the house and gave one to the master sailmaker and one to the gun captain.
Helmsman - Mutineer
The helmsman was a Mutineer, so I thought it would be fun to give him a sidequest that would go a bit against his starting faction. He had to find a weapon and give it to the Pilot so that they could protect themselves if things got out of hand.
Master Carpenter - Loyalist
I didn’t know if this player was able to stay for the whole game, so I gave him a shorter quest. He had to buy drinks for a few sailors from other factions and try to speak a bit to them to understand their troubles.
Survivor - Loyalist
The survivor was found at the same time as the chest and the dagger that were buried on this lost island. He’s amnesiac and couldn’t really recall how he ended up here. He’s very grateful that the crew of the Crimson Fox rescued him. He had to find 5 other sailors who would vouch for him so that he could join the crew as a permanent member.
Master sailmaker - Curseseeker
The master sailmaker had to start an argument between the lookout and the gun captain, who started to question her skills.
Rigger - Loyalist
The rigger was also a fence onboard. Selling and buying anything you might need. Their quest was to amass more than 10 gold coins. To help them in this mission, they also had a list of what they recently talked about, bought, or sold for some people. This could be useful intel because the NPCs were telling people looking for specific items that the fence might help them find them.
Surgeon - Curseseeker
The surgeon was using too much alcohol for their patients, which brought down on them the fury of the Storekeeper NPC. They had to repair this relationship.
Lookout - Mutineer
The lookout had to watch their back. They needed to form a strong alliance with at least one sailor from another faction, and if possible, with one from each of the other factions.
Gun Captain - Loyalist
The gun captain had to win three of the four games hosted by the NPCs to prove to everyone that they were the best onboard.
Cabin boy - Mutineer
This ambitious young pirate had to obtain a better post, hopefully skipping the rest of their stupid training and immediately getting a full part of the loot.
Mate from the French Royal Navy - Loyalist
This mate got very, very drunk last night and lost the two keys necessary to open his stash. He needs to find them at all costs. He didn’t know where they were, but I gave one of them to the Master Carpenter, and the other one to the gun captain (It was meant to go to the Captain from the other ship at first, but I had to move it at the last minute).
Captain from another ship - Loyalist (didn’t end up playing)
This Captain had lost his precious telescope, and what kind of Captain loses his telescope? He had to find one on this ship. The helmsman has a telescope.
Conclusion
And that was it for the plot preparation!
I wrote a few lines for each player to give them an explanation of what they did onboard, and with which faction they had an initial affinity. I also had a call with the four NPCs to explain to them in great detail the plot for each faction. I needed them to be able to give hints or slow down players, improvise on-the-go interactions with different persons, and keep the whole thing running.
So to recapitulate, I planned the whole game like this:
-
Set the scene, get a general idea for the main plot
-
Create the structure for each character
-
Design the factions, goals, and members
-
Write the introduction that would be given to each player before the game
-
Add some social activities with mini-games and a bar
-
Finish the characters by giving them a personal quest and an item each
See you in the next post to talk about how to make the props!