The Grave of Calico Jim is where the (decently famous) Calico Jim left all of his treasures shortly before he was caught and executed. His corpse was later recovered by a dear friend, and interred in this grave. Jim’s (relatively) benign ghost now haunts his tomb, awaiting the day that his treasure is rediscovered and taken back out to sea.
In my pre-campaign survey, I asked my players what they wanted out of this campaign. One of them asked me to have them “go on a real pirate adventure”. This request got a little out of hand, and resulted in my Pirate Isles…
After wracking my brains for a while on how to do a proper “treasure map” adventure, without grinding my game to a halt, or forcing myself to make multiple copies of survey-style maps of fictional places (so my players could reasonably experience the geography of a particular isle), I gave up on that. Instead, I decided to gloss over the whole “follow the map to the treasure” part, and gave them a dungeon with traps, riddles and puzzles. Following that design philosophy, I was heavily inspired by The Goonies.
Calico Jim’s name was taken from “Calico” Jack Rackham, an actual pirate of the caribbean. Parts of his story, and Mark/Bonny Reed’s story, are taken from the real-life accounts of the pirates Anne Bonny and Mary Reed.
Calico Jim was a reasonably successful Tabaxi pirate of the Pirate Isles who repeatedly managed to slip through the fingers of the Elven Navy. Jim’s first mate was a dear friend of his, a half-elf named Mark Reed. Due to Jim’s infamous alcoholism, the big, successful catch always seemed to just barely slip through his fingers. Jim was captured in port one night, after he had passed out drunk in a tavern. Despite Mark’s efforts to jailbreak him, Jim was executed by beheading. Mark later stole Jim’s remains, and buried them in a pre-designed tomb. Jim’s fortune, and his infamously speedy ship, Fair Anne, was never seen again after Mark returned Jim’s remains to The Isles.
Calico Jim was actually a female Tabaxi, named Anne-of-Three-Colors. Mark’s real name was Bonny; she was the illegitimate daughter of an Elven nobleman and his human mistress. It may be a clue to them that Jim is a calico… In real life, male calico cats are exceedingly rare, due to how coat color genetics happen. Throughout this document, I will refer to Jim as “he”, but only so that you don’t slip up when talking to your players. Jim is entirely female, and "his" reasons for hiding his sex/gender are for you to make up. The exact nature of "his" relationship with “Mark” Reed is also up to you to interperet. Jim can be as long-dead, or freshly-dead, as you want him to be. In my setting, I did not describe how long ago he died.
If you go the treasure map route, you should have the players end up on a sharp, steep cliff that overlooks the sea. You may or may not choose to have an X mark the spot. If the players begin digging (or Move Earth), they should find a small monument buried under the ground. Pouring out a serving of alcohol on the headstone will cause Jim’s ghost to appear.
Here lies Captain Calico Jim.
A true friend, companion and quite daring cat.
Cursed be curiosity.
Were it not for the mystery of what lie at the bottom of that bottle
Jim might not have died.
Fifty paces east, and you may find Jim’s treasure.
Calico Jim’s ghost will be a translucent blue tabaxi with a calico pattern. Jim’s head will wobble unsteadily on his body, as he died by decapitation. He will be dressed in ragged jail-clothes, but he will have a tricorn “captain” hat, and will periodically drink from a flask hidden in the ragged jail cloths.
Jim’s ghost should be friendly, but not at all helpful, in raiding the tomb. Should the players act with hostility to Jim, he will attack. If outside of the tomb, Jim will have stats comparable to a wight. If inside of the tomb, he should be like a combination of a ghost and a non-spellcasting mummy lord. Because Jim was a swashbuckler rogue in life, he should have abilities comparable to a level 14-17 swashbuckler rogue. Jim will not necessarily turn hostile to the PCs unless they attack him first, or begin defacing his tomb in some way. If they defeat Jim, he will respawn in the secret grotto after 24 hours, and need to be resummoned. Jim will not be hostile after being resummoned. Think of Jim’s ghost as something like a mix of Jack Sparrow and Peeves from Harry Potter.
Note that the grave marker itself is only twenty or so paces from the edge of the cliff. The entrance to the cave is thirty paces down the side of the cliff; it is illusioned so that the entrance just looks like the sheer face of the cliff.
Once they actually enter the tomb, they will see a dark tunnel dug in to the cliff. The walls and stairs should be slick with mold, slime or water. As they round the corner, they should be met with a magically sealed door. This door can only be opened by Calico Jim, Captain Reed, or a wish spell.
Jim will watch passively as the players try various ways to open the door. After they give up in exasperation, or if they ask nicely, Jim will playfully offer to open the door if they answer his riddle.
R -“Recite my favorite part of Corsair’s Law!”
A- “First and foremost, these laws must only be held as guidelines for the proper conduct of thieves, cutthroats, swashbucklers and rogue adventurers upon the sea of treasures.”
Note - This dungeon originally took place in my Pirate Isles setting. Corsair is a pirate god who set down the social laws of his pirate islands. It is forbidden to write these laws down, so nobody has a firm grasp on what all of them are (My player have begun to correctly suspect that I’m making up Corsair’s Law as I go). Corsair’s law is fairly analogous to the Pirate Code of Pirates of the Caribbean. You can change “Corsair’s Law” to “The Pirate Code” or something. The answer remains the same.
Hardmode - You can give your players only one answer apiece.
This room is filled end-to-end with artwork, mostly raided from Elven temples and beachfront estates. Paintings, tapestries, wood carvings and stone statues. Most of the artwork has been severely ruined by being stored in a room so close to the entrance, and the humidity of the ocean. Around 80-90 % of it is unsalvageable, even by magical means. This room is a fakeout; designed to trick the players into leaving after seeing that Calico Jim’s treasure hoard is just a pile of junk. The door to the next room is buried under a pile of “artwork junk”. Once it is revealed, Calico Jim will state,
“Tis’ rude to approach a captain’s funeral feast without an offering.”
The players will have to offer him some alcohol. Preferably rum, or fine elven wine, but anything alcoholic will do.
This hallway is 25 feet long (This is important!). The entire hallway has illusion magic on the walls that depict daring heists that Jim and Mark committed during their career (in reality, these illusions on the wall are there, so that a “detect magic” spell is interpreted to be revealing the illusions on the wall, and not the illusion hiding the spike trap).
In the very middle of the hallway is a heavily hidden spike pitfall trap. The floor over the spike trap is a flimsy “film” of earth that will not crumble under the weight of a small creature, such as a familiar. Nor will it crumble under the weight of a long tapping-stick. A DC-18 perception or investigation check should reveal a slight difference in the floor.
The fall into the spike trap should be dangerous, but not deadly for your players’ level. The spike trap should cause poisoned condition, if they fall in.
This room is a macabre dinner scene with multiple dessicated bodies seated at a long table. Fine Elven china and dinnerware are set up as though a feast is about to be served. The dead bodies are the corpses of those who have slept inside Jim’s tomb (Jim may or may not choose to warn the players about this). If your players decide to examine the corpses closely, they should be unable to determine a cause of death, as the corpses died in their sleep. If you would like to make the “DO NOT SLEEP!” rule more explicit to your players, you can have a more “fresh” corpse sitting at one of the places. If asked, Jim will make up various stories about who these people were. If any “speak with dead”-type spells are cast, the dead person should be unsure of what killed them. They would be quite hostile towards Calico Jim, and the last thing they remember is going to sleep after being injured in the tomb. Until the secret grotto is discovered by the players, Jim will not tolerate theft of the silverware.
Easy Mode - Have some of the corpses show signs of dying to the traps in the lever room.
This hallway is twenty feet long (important for later!), and it has the same sort of fantastical illusion murals as hallway 1. 5-10 feet in, there is the same sort of spike-pit trap as hallway 1, but there is a trap door in the bottom of the spike pit; it is hidden below a large spike, with a skeleton impaled upon it (Skip to Secret Hallway if your players find this trap door). The door to Room 3 is also locked. Jim will freely open this one, and offer a bit of helpful advice on what to do.
“Vanity will aid ye here.”
Note - Prior to entering this room, force your players to write down how much gold they have on a piece of paper, and hand it to you. This will make them very paranoid, and it will come in handy if they pull the gold lever.
This is a room with many levers on the wall. The levers will not do anything until the entire party is inside the lever room. As soon as the last party member enters the room, Calico Jim will seal the door. The door on the opposite wall will not open until the flat lever is pulled.
Steel Lever – A dangerous amount of electrical damage to the person who pulled the lever. No save.
Wood Lever – Arrows will spawn and rain down upon the lever puller. Roll to attack for 6 longbows, +8 to hit.
Painted Lever – This lever is flatly painted on the wall in blue paint. The players will have to hold a mirror up to this lever, and watch their reflection pull on the lever. This will open the door to the next room.
Silver Lever – A fragrant smell of lotus flowers will fill the room. It is poison gas; DC-18 to save against the damage. Half-damage on a save. 6d6 poison damage and poisoned condition on a fail.
Solid Gold Lever – The players’ money will begin doubling. They should not notice this until 30 - 60 seconds has passed. Start a stopwatch, and every 6 seconds, the money in the room will double. Depending upon how rich your players are, it may take 4 - 5 minutes before this actually becomes a problem. Eventually, the room will fill up and the players will begin to take bludgeoning damage. Remember that due to how doubling works, the room should fill up 6 seconds after it is half-filled. Once the players leave the room, the magical money will disappear. A level-5 dispel magic should stop the doubling effect. Should they fail and “die” here, have them pass out and wake up naked outside Calico Jim’s tomb. Alternatively, Calico Jim could attack them after he dispels the magic coins.
Fancy wood and blue gem lever – Nothing happens. Let your players wildly speculate on this.
Calico Striped Lever – Everyone in the room makes a DC-17 WIS save. On a failure, take 6d6 psychic damage, and become totally colorblind. Color vision cannot be returned until greater restoration or stronger is used.
Green – 3 greater healing potions appear on the floor. They are in different colored vials. Allow your players to feel paranoid about these vials. Pulling the lever again will not make more appear.
This hallway is the exact same as hallway 1. You may have different murals on the wall, if you are that descriptive. The door to room 4 is not locked, but your players may assume it is. If they assume it is locked, Calico Jim will demand that they sing him a sailing song. Jim will watch with a smirk on his face as they attempt to please him with songs.
“’Member ta set yer sails upon the sea and sing a jaunty tune!”
There are no gimmicks in this room. It is a small reading room, with a driftwood chair and some oil lamps. There are a few shelves on the walls with books, journals and maps. The journals are Jim’s personal journals from when he was alive. If you wish to have any plot-relevant revelations here, this would be the place to do so. Many of the books have a transmutation magic about them; it is a common treatment for paper in the Pirate Isles, so as to preserve it out on the seas. This is also a handy place to store some magical scrolls, or something. Try to lull your players into a false sense of security in this room; if they are the types to sleep in dungeons so that they can have the benefits of a long rest, this is where they may attempt to do so.
Exact same as Hallways 1 and 3. The door in to room 5 is locked. Calico Jim will possess the door, and playfully demand a “door joke”. He is being intentionally vague; you have to tell a knock-knock joke. Any knock-knock joke will do. (This riddle made one of my players want to die.)
This room is totally empty. Illusion magic depicts all of the adventures that have been seen on the walls in the previous rooms. The players will have to find the secret door on the south-east corner of the room. The secret door is hidden behind about a foot of solid stone, but the stone is a different color than the rest of the stone in the room (the illusion magic initially hides this). Once they find the door, it is unlocked.
This hallway is plain, but it is the same length as hallways 1, 3 and 4. There is the usual spike trap in the very middle of the hallway. There is an apparent dead-end at the end of the hallway, but it is an illusion. The wall will give way into a strange, long sort of “chapel”.
As soon as a player rounds the corner into the chapel, Calico Jim will have a strange fit and disappear. Allow your players to speculate why. (It is because he couldn’t stop giggling. He LOVES this next prank!)
The chapel is 45 feet long, and ten feet wide. At the very back of the chapel is a strange altar, carved out of the surrounding stone. A few small artifacts are laid on the altar, including Jim’s hat, a compass and a locket showing a picture of a half-elf woman, and a tabaxi woman (pictures of Bonny Reed and Anne-of-Three-Colors). The altar is not dedicated to a god, but to Anne/Jim and Bonny/Mark’s friendship.
Now, this entire room (except for the altar) are on a sort of seesaw. Imagine the floor of this room is the flat plane of the seesaw, and the altar is holding the floor level (by keeping the seesaw from rising up into the ceiling). Depending upon the race/class makeup of your group, the seesaw of the room should come unbalanced as more of the group approach the altar. The tipping point of the seesaw should be ~10-15 feet into the room. Do your own handwaving/calculations to determine how much weight each party member should count for.
As soon as the seesaw begins to tip, tell the players that a wave of heat and sulphur blows out from under the altar. Have everyone roll initiative.
Each player may use their move action to make a difficult acrobatics or athletics check and move 5-15 feet towards the door. If they succeed by more than 5 points, they may use their dash action to move an additional 5 feet. You cannot move through another player’s space without causing them to slip (they roll their next check with disadvantage), or using up 5 feet of movement. On initiative count 0, the seesaw tips further and everyone should slide backwards 5-10 feet. Also, the DC to run up the seesaw increases by a few points.
As the seeasaw tips further, the players should be able to see a bubbling pool of lava beneath the altar. They should also hear Calico Jim’s mad cackling as they slip and scramble not to fall in. Anyone who slides down past the altar is “dead”.
When enough weight gets past the pivot point of the seesaw, it will rebalance itself. Now, the lava pool is an illusion. When a character slips down there, they should see a message painted on the wall in rough characters
“Ye’ve come the wrong way! Look back on ye map and go back to the even one out.”
This is referencing the secret trap door in hallway 2. You will notice that each hallway has an odd length, except hallway 2. If your players are totally stumped, they can ply Calico Jim with alcohol.
Calico Jim should reappear once the players have discovered the lava is an illusion. He will be laughing hysterically. “You lot should have seen your faces!”
After finding the trap door at the bottom of the spike trap in hallway 2, the players will find themselves in a secret hallway. There are no traps here, but feel free to populate it with (dead-dead) skeletons and spiders, to make them paranoid. The door to room 6 will not open, unless the players can say the name of Calico Jim’s best friend (Bonny Reed).
Note - Unless the players read it in the library, saw the locket in the chapel or have some other kind of outside information, they should not know that Mark Reed’s real name was Bonny Reed.
This room will be set up like the captain’s quarters of a ship. Two beds will be present; one for Jim and one for Mark. Jim’s corpse will be on a bed, with some kind of necromantic magic keeping it looking (relatively) fresh. The players may note how the head has been severed from the body. Depending upon what you’re doing with your game, you may or may not have Mark’s body in the bed next to Jim. If Mark is there, they should be holding hands. If Mark is not there, but IS deceased somewhere else, Jim should be oddly melancholic. If the players do anything to desecrate Jim or Mark’s bodies, Jim will fly into a rage. Mark’s ghost may or may not appear, depending upon how difficult you want the fight to be. The door that leads to room 7 should be locked.
Jim will say, “Before I open the way to my store of treasures, you have to tell me… What was the secret we took to our graves?” or “What was the secret I took to my grave?” or “What was the secret Mark went to such trouble to keep hidden?”
The answer is that Jim or Jim and Mark were women. After the players answer this, Jim will disappear for good.
No tricks here. I had originally intended to put an additional door on this room, but I forgot to erase it on my map. The way into room 7 should be obvious, so that the players overlook the illusioned wall that hides room 8.
This is a false treasure hoard that has apparently already been raided by another group of adventurers. Your players may find some loose gold coins, or a small amount of jewelry. There is a random sarcophagus in the corner, and a skeleton inside it. Speak with dead will reveal that it is someone who was buried here way before Jim had it excavated and turned in to HIS tomb. The corpse will reveal the existence of room 8.
All the wealth and riches of Calico Jim’s infamous career are hidden here. The eastern wall is a very thinly constructed stone wall that can be broken to reveal a hidden, artificial grotto. The players should experience great difficulty in transporting it out. Of particular note is a gallon-sized glass jug. When detect magic is used, the jug should almost radiate transmutation magic. Populate this room with whatever other treasure you like.
This is an artificial grotto that hides the Fair Anne. The ship can be transported out of the dungeon if a player holds up the magical glass jug from the previous room, and looks through it as though the Fair Anne was contained inside of it. This will cause the ship to be inside of the bottle until it is placed back into the water in a similar manner.
Jim's flag (a patchwork flag of yellow, black and white cloth) is still flying proudly over Fair Anne. Unless the players return the flag to Jim by placing it over his corpse in the grave room, Jim will continue to semi-maliciously haunt the ship.
Note - Save yourself some headaches. Do not allow the glass bottle to contain any other ships. Do not allow the bottle to just drop a boat on a losing fight.
