At the city’s main port, the party spots a sea captain struggling to walk to his ship. The reason for his sluggish step is obvious; a skeleton, dressed in garish costume, is gripping one of his ankles and being dragged along behind him.
“You need to quit doing this every time I drop anchor, Roger,” the captain says with a groan, “Can’t you see that groveling like this is only making you look more pathetic? Now, get off of me!”
He gives the skeleton a hardy kick with his free foot and sends bones scattering about the dock.
“Oh nooo!” the skull cries out as it rolls away and splashes into the nearby shallows.
At this point, the party can choose to hop down onto the beach and rescue the submerged skull.
“Ahoy and thanks, me mateys,” he says, “The name’s Captain Roger. If I can trouble ye for another favor, could ye help put me back together again? Everything sort of magically snaps into place. I just need a wee bit o’ help gettin’ myself arranged.”
When assembling the skeleton, have a player roll a Medicine check to determine the anatomical accuracy of the recreation. If the roll fails a DC 10, then the legs/arms will be mixed around, but Roger still politely comments, “Close enough” and continues on.
“Ye are all such kindhearted landlubbers. I’m not used to people stoppin’ and helpin’ out me kind. Bein’ a pirate doesn’t earn much sympathy, ye see, and bein’ a skeleton pirate is even worse!”
He sighs. “I was quite the notorious buccaneer back in me day. Sadly, me pillagin’ and plunderin’ was cut short by a tragedy…I was tryin’ to feed breadcrumbs to some seagulls, ye see, and tripped over me bootstraps, fallin’ overboard. Me crew was moored off an island at the time, in the shadllows, and I caught a rock to me face.”
He shakes his head somberly and buries his face in shame. “That’s when I earned me nickname…the Folly Roger. Now, I wander these docks, lookin’ for someone to help restore me pride. Ya see, I just want to go down with me ship, in spectacular pirate fashion. I don’t even need a real battle. Just let me play along while ye blast me ship full of cannonballs. Send me to me watery grave. What do ya say? In return, I can show you to me buried booty, and everything there can be yers.”
If the party agrees, he will ask them to follow him to an isolated cove where his ships are kept.
Staging a Showdown
The “ships” Roger was referring to are not the mighty, awe-inspiring pirate vessels from his prime but modestly sized keelboats. One of the vessels sports a smiling skull flag (Folly Roger’s vessel) while the other ship’s flags are completely clean/white (the players’ vessel).
The voyage out to sea is fairly uneventful, with the players closely tailing Roger’s ship. Seagulls begin to soar above the pirate, landing on his vessel. Players can watch as Roger excitedly scampers across his deck, from seagull to seagull, putting small paper pirate hats on their heads. “What a fine crew, we have here!” he shouts triumphantly. “You would have to be a fool to cross swords with this fearsome bunch!” He turns around and gives the party a thumbs up.
Eventually, Roger’s ship slows to a halt, prompting the players to bring their own vessel to a stop.
Suddenly, Roger turns around to face the players, pulls out a small spyglass from his jacket, and points it in the direction of the party’s ship. He gasps loudly, feigning surprise, and hollers, “We’ve been followed, men! To yer battle stations! Don’t let ’em take us alive!”
At this point, the sea “battle” begins. Being in a keelboat, players have a ballista at their disposal (although feel free to substitute for a cannon). When preparing to fire, roll either a straight Intelligence check (to calculate proper mathematical distance from the target) or a Sleight-of-Hand check (to carefully adjust the angle of the ballista). Once the weapon is fired, the heavy arrow/harpoon soars through the sky; any rolls passing a DC 12 rip into the side of Roger’s ship, punch holes through his flag, or tear across his deck, ripping up planks of wood.
With each successful strike, Roger pretends like he’s distraught and says things like, “Blast, those landlubbers! Steady now, men! May they rue the day they crossed our path!”
Roger returns fire, but he always intentionally launches his ballista arrows either too short (directly downward into the water) or too wide, so that they never put the party in any real danger.
Finally, when the opposing keelboat reaches 0 HP, any remaining seagulls that haven’t taken flight already will abandon ship and take to the sky. Roger’s vessel begins to quickly take on water.
The pirate captain looks tremendously excited about finally getting his honorable watery grave, clapping his hands eagerly as his boat gurgles and sinks into the choppy ocean waves.
“Argh, it seems that I’ve been bested!” he grumbles, shaking his bony fist at the players. “Now it’s time for the brave Captain Roger to go down with his ship!”
He strikes a valiant and dramatic pose as he prepares to disappear into the murky depths…when the ship stops.
Puzzled, and more than a little agitated, Roger steps to the ship’s railing and peers down over the side; something has stopped him from sinking.
Suddenly, there is a great bubbling and frothing of the ocean waters. A muffled but deep groan resonates from the fathoms below. Now, Roger’s ship begins to rise…and rise…until it’s apparent that the Folly Roger’s ship has become marooned on the back of a giant Dragon Turtle.
Thar She Blows!
The gargantuan beast from the murky ocean depths is furious, having been awoken from its nap by all the commotion overhead (and with a shell full of ballista arrows thanks to Roger’s intentional misfires). Not being able to see the pirate captain or the shattered remains of his vessel (since both are now stranded helplessly on the monster’s back), the Dragon Turtle focusses its fury entirely on the party.
Provided that the party didn’t waste all of their ballista ammo taking down Roger’s ship, they can use this ranged weapon to strike the monster from a distance.
If the ship’s HP reaches zero, however, it will begin to sink, forcing the players to float upon pieces of debris or transport themselves to the back of the Dragon Turtle’s back. Captain Roger can do his part, perhaps outfitting his ballista with a spear and rope, firing it into the sea in an attempt to help pull the players onto the monster’s shell.
When the monster is finally defeated, it groans and sinks back down into the ocean. A little less confident this time, Roger waits with bated breath to see if anything bigger than a Dragon Turtle stops the beast’s corpse from sinking. When he trusts that he is, in fact, finally going to get his honorable burial at sea, he reaches into his jacket pocket and pulls out a bottle with scroll of parchment inside.
If a player is close enough, he will toss it to them directly. Otherwise, the bottle lands in the water where it stays, floating, until a player is able to retrieve it.
Opening the bottle reveals Captain Roger’s Pirate Map, which you, as DM, can use to segue into another sea-based adventure. Of course, if the keelboat is still afloat, the party has also gained a new mode of transportation.
Also, for added ridiculousness, consider adding a small magic ring in the bottle as well. This ring is dazzling and sparkly silver, featuring an ominous skull design. When identified, this piece of jewelry is called the Scullyswag.
When worn, the ring grants advantage on any sleight-of-hand checks that are made when trying to steal something. Additionally, it has one charge every 24 hours that can be used to invoke one of the following strange effects:
- “Yo, Ho, Ho and a Bottle Of Rum”– Touch a container of liquid (less than or equal to 1 gallon) and instantly turn its contents into delicious, high-proof rum.
- “Shiver Me Timbers” – When activated, anything made of wood within 50 feet of the player begins to shake violently for 1 minute; this can be used to shake out creatures hiding in trees, convince someone that a house is haunted/a storm is coming, etc.
- “Booty Call” – When activated, any hidden gold or gemstones within 50 feet of the player will begin to sing out/whistle to be found (only the wearer of the ring can hear these sounds).