Captain Beatrix, a Tarraconese carpenter and hustler. Leads by confidence and example.
John Wex the Bastard, a literate sailor with a love of tall tales.
Margarita Duerte, Tarraconese blacksmith and secret practitioner of the dark arts.
The Crew. Yes, the Crew are a PC. Some are seasoned pirates, some are Chultan villagers.
Three weeks west of Chult, the crew spotted a small rocky island not marked on any chart. Hopes of turning it into a pirate hideout were quickly dashed. The "island" was, in fact, the back of a giant sea-turtle. While John Wex was delighted to see an ancient myth confirmed, the rest of the crew insisted on sailing away as quickly as possible.
After another two weeks as sea, the ship sailed through a group of small wooden boats. Lit only by the moon, the crew peered over the rails at the swarm of empty vessels. "Shipwreck?" Margarita speculated. John Wex volunteered to board one and search for clues. To his shock and dismay, he discovered the boats were, in fact, boat-shaped lobster-things floating on the surface of the sea. He escaped with a few deep scratches. The crew opened fire from the deck of the Magnificent and steered away from the false-boats.
"This sea is cursed," John Wex said, spitting over the side.
"They don't call it the 'Isle of Happy Fun Times' ", Margarita sighed.
After three more weeks of calm sailing, with fresh water running low and "dancing rice" infesting the flour, the lookout spotted an unmoving bank of clouds on the horizon. The next day, the top of a plateau and a thin green line of trees moved into view. "Land ho!" the crew shouted.
"Don't be rude," Captain Beatrix said, "we'll make land when we make land."
The pirates approached the island from the southwest, staying well off the shoals and steering for the distant smoke of cooking fires. There were no signs of "proper" civilization; no other ships, no docks, no church towers. Several peaks on the island appeared to be volcanic. The rest was jungle, rocky spires, and mist-shrouded highlands.
Three small canoes rowed out to meet the Magnificent as she sailed east. The olive-skinned locals didn't speak any language the crew could understand, but Beatrix managed to convey non-hostility, friendly intentions, and willingness to trade. The canoes lead the sloop to a small village. None of the islanders appeared over-awed by the ship, indicating that this wasn't their first visit from an old-world vessel.
Very wisely, Beatrix decided on an initially cautious policy. She offered iron goods and even weapons to the local leader, an imposing and stout gentleman with a few gold rings and piercings. Slowly convinced of the crew's good will, more and more sailors were allowed off the ship. The villagers organized a feast of pork, fish, and a hundred kinds of mysterious plants. The crew ate heartily.
After the feast, the crew was delighted to discover that many of the locals were willing to offer more than food for iron and rum. The crew stripped the Magnificent of every small portable iron good they could find. For the rest of the journey, the entire crew - apart from the captain and quartermaster - ate their meals using one spoon passed from hand to hand.
Two days later, more canoes arrived from other islands to examine the curious ship and scruffy-bearded pirates. The new arrivals brought an interpreter; a captured slaver from an ill-fated raid. The slaver cursed and swore and hopped in circles, demanding freedom and vengeance. Captain Beatrix wrung all the information she could out of him, used him as a translator, found out the locals got their gold from "the Forbidden Island" to the north, thanked him, and sent him back into captivity.
The next morning, the Magnificent sailed north through the island channels. The much larger "Forbidden Island" was cut off from the rest of the chain by a huge basalt wall, built by techniques no old-world mason could fathom. Each block was the size of a cottage, fitted without mortar and carved without chisel marks. The crew stocked up on supplies, loaded their guns, and marched through the shallow bay on the north side of the wall. It was a grand expedition to the Isle of Dread.
It went about as well as you might expect.
2. The party tried following an ancient half-overgrown road. They encountered a truly gigantic four-legged lizard that seemed to breathe acidic fog. They fled into the jungle and got lost.
3. While making camp, John Wex discovers a buried structure. It appears to be some sort of dry well or air shaft with an iron grate at the bottom. The group ignores it and settles down for the night.
4. The next day, John Wex and two pirates descend into the underground structure. They find a large frog idol with ruby eyes. John pries out one of the eyes, releasing a stream of clear liquid. He pries out the other eye, doubling the liquid flow, then decides to test if it's flammable by touching it with his torch.
5. The resulting explosion kills one of the crew member, destroys John's left eye, right arm, and most of his skin. Screaming and flailing, John is hauled to the surface and given the best available medical treatment: rum and rag bandages.
6. That night, several crew members are attacked by "ghoul-like" humans from the air shaft. The pale cannibals are driven back.
7. The crew mounts a full expedition into the underground structure. John Wex and two crew members are left on the surface.
8. The expedition disables a pit trap, discovers evidence of more ghoul-people, and finds a gigantic spiral staircase leading downwards. They descend and are attacked by a huge flying snake monster.
9. An epic fight ensues. The crew take many, many casualties. Captain Beatrix is swallowed by the snake and dies. Margarita, with near-suicidal bravery, destroys the creature's three ruby eyes, turning it back into stone. The creature's blood solidifies into rubies. The surviving crew members are rich beyond their wildest dreams.
10. On the surface, John Wex and his minders are attacked by ghoul-creatures. John decides to descend into the underground structure to search for the crew; they should have returned by now.
11. Unaware of the now-reset pit trap, John Wex falls in. A 8" iron spike punches through his head, poking out his other eye and shattering the socket. He is rescued by the crew.
12. Three days later, the remaining survivors drag both John Wex and huge sacks of rubies back to the basalt wall.
13. More crew members die to deadly spiders in camp. Their bodies are used to distract the crocodiles. The venomous spiders are stored in jars for later use.
14. Much diminished, the pirates flee the Isle of Dread for the safety of the Magnificent.
Blind, miserable, and on death's door, John Wex insists on being left with the islanders. He hoped his share of rubies and some hoarded gold will be enough to make his final days pleasant, or possibly enough to fund a slow and painful recovery.
The surviving crew elected Margarita Duerte as Captain.
Another group of islanders "trade" one of their captives to the pirates; a banker captured by the slavers and briefly held for ransom. Dorfina von Dusseldorf was delighted to be rescued. She was less delighted to find her saviors were pirates who immediately elected her quartermaster "for her figuring with numbers was beyond the knowing of the rest of us."
At Margarita's direction, the Magnificent set sail back to Chult. One last reminder of their time on the Isle of Dread reared its head after they were out to sea. A princess of the islands, named Celeste by the crew to avoid learning a new language, had crept aboard to see the world. Her haughty manners and strange beauty entranced the crew. Captain Margarita, baffled and a bit annoyed, tried to teach her as much Tarraconese and sailing knowledge as she could.
With sacks full of rubies resting in the hold, the pirate crew could now afford anything they could imagine. But would they live to spend their treasure, or would the unforgiving sea claim them?
Find out next time.
It was kind of amusing to have Beatrix's player go, "These people really like rum! We could trade them a lot of rum for all their valuables, maybe set up a trade route, get them hooked... oh dear."
The PCs have take a fairly negative view of slavery for various in-character reasons. They're not going out of their way to wreck the trade, but opportunities to profit by it have been vigorously declined.
When speaking in character (as the captured slaver or other NPCs), it makes sense to refer to the islanders or Chultans as "savages" or "tribesmen" or "pygmies", etc, because that's how the NPC would see them and frame the discussion. Out-of-character, I've been very careful to stick to neutral descriptions. The players, consciously or not, seem to have picked up on the distinction.