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Previously on Tomb of Annihilation

Mannix, level 5 Human Inquisitive Rogue/Wizard
Khaless, level 5 Half-Drow Assassin Rogue
Gillian, level 5 Triton Bard of Whispers
George, level 5 Tortle Battle Master Fighter/Rogue
Therin, level 5 Hill Dwarf Druid of the Moon

With one pirate captain defeated and the ship captured, the party could interrogate the surviving crew (namely the first mate, Mad Kalita). They learned the specific location of the pirates’ secret hideout, Jahaka Anchorage, as well as the guard shift tactics the pirates used.

Armed with about half a plan, the party used the Dragonfang to draw in close to the Anchorage and deal with the second pirate ship, the Emerald Eye, before infiltrating the pirate base.

Pulling information out of Kalita ended up being more of a role-playing exercise; I don’t think I even had the PCs roll a Charisma check. I liked that they basically convinced her to become an adventurer under their employ, and she agreed to give up her pirating ways.

She revealed that of the three pirates in league together, one was always resting at their hidden anchorage, one was out guarding it, and was one out doing pirate stuff. They could use the Dragonfang pirate ship to get in close (the Pegasus would be fired upon and chased), but they’d still have to convince Captain Al-Saryak why Captain Jaharwon isn’t aboard their ship, and who they hell they are.

The party wanted to employ the same tactics they used with the Dragonfang. Get in close, let the captain board the ship, and stealthily take him out.


The close part worked, even if the magical Tiny Hut right in the middle of the ship was a tad suspicious. Gillian did the talking, trying to convince him there was a “treasure problem” on their ship. Al-Saryak was instantly smitten with the exotic triton, going so far as to ask to buy her for his ship. She didn’t take kindly to that, whipped out her crossbow, and shot him! Roll for initiative!

This could have been another session-long battle or pirate on pirate action. But Khaless followed up Gillian’s shot with an assassin powered crossbow bolt of her own, dealing tons of damage to the Captain, while Therin cast Wall of Thorns via his magic staff, thrusting up a deadly wall all along the enemy ship, killing several crew members, and finishing off Al-Saryak. Didn’t even get a single round!

The fight lasted maybe another round after that as the berserker first mate clawed through the vines to attack the Therin-bear that had boarded his ship, but he was quickly targeted and swarmed by the PCs. George boarded the ship from behind to kill a pirate, but once the first mate fell they quickly dropped their weapons and surrendered. It seems a blitzkrieg strategy worked just fine!

The PCs tried to convince one of the random pirates aboard the Emerald Eye to switch sides and head up to Port Nyanzaru. They thought it would be a great idea for the pirates to turn the ship in and collect the reward, even though the harbormaster would surely just arrest all the pirates. Not to mention the pirates won’t go anywhere near Aremag the dragon turtle.

The PCs really wanted to keep all these ships they were collecting (and get the eventual 2,000 gold bounty for each), even though they had no logistical way of doing it. It was cute listening to them put blind trust into these pirates they had just met, then letting them go.

With the Emerald Eye taken care of, they sailed onward to the final pirate crew and the hidden base, a cove tucked under a cliff in the north of the bay.

Kalita knew how to get inside without crashing on the rocks, but the anchorage was too crowded with one ship already docked, the Stirge, and the Dragonfang wasn’t due in for another week.


Once again the PCs arrived with half a plan, and seemed unsure of how to handle this area. Mannix suggested firing upon the tavern, an overturned, converted ship that served as the pirates’ main resting area, as a distraction. But Kalita warned that would stir up the hornet’s nest.

Instead the PCs called out that they needed help, that their captain was injured. A small row boat was sent out to investigate while the watchtower above the tavern looked on. Using Pass Without Trace the PCs slipped into the water and swam a few dozen feet around the south end, sneaking toward the tavern, right under the guards’ noses.

Oddly the PCs then told Kalita to sail away as a further distraction, essentially giving her a free pass to escape from them the way the Emerald Eye did. It will be interesting to see where Kalita’s loyalties lie.

The half-a-plan party waltzed into the tavern. It was full of pirates drinking, carousing, fighting, and laughing. They acted like they were supposed to be there, as envoys of the Flaming Fist, the pirates’ partners in crime.

But the third pirate captain, Laskilar, had heard of these adventurers and their growing fame in Chult. He instantly recognized their motley crew of triton, tortle, and half-drow. What followed was a deliciously tense sequence as Laskilar threatened the party to give up the treasures they’ve found in exchange for their lives.

Player characters will never give up their hard-fought loot. Khaless answered the negotiations by stabbing the nearest pirate as the tavern explodes into a good ol’ fashioned bar brawl. Two down, one to go!

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