This week, prior to pillaging some pirates, a prince perpetrates an appalling plan of pernicious payback upon the party.

When last we left or heroes, they journeyed back to Port Nyanzaru to begin the much-anticipated Pirate Plunder subplot. I have other subplots that I would rather run, but my players insist on killing scallywags, so that’s what we’re gonna do. Eventually. Along the way, we said goodbye to the campaign-ending Artus Cimber, recovered an heirloom for some useless lycanthrope, and rescued a campaign-saving Aacockra.

My players were eager to jump into the pirate killing, but since Roland had to miss another session, I delayed my crazy pirate plans. Instead, I ran some homebrewed encounters to tie up some loose ends with some of the more irritating citizens of Port Nyanzaru. Specifically, I wanted to deal with the evil Merchant Prince, Kwayothe, and those glory-hog guides, Faroul and Gondolo.

But first, we run through the usual RPG crap whenever a D&D group gets back to town; inventory management, gold exchange, equipment purchases, and check-ins with the quest giver NPCs. I do at least appreciate that Chult’s nonsense has its own unique flare. We check in with Meepo, the kobold zookeeper, on the status of the meager menagerie the players were hired to capture for their patron back in Waterdeep in what seemed like ages ago. I love that what began as a silly safari has turned into a desperate quest to save the world. Pretty cool.

Next, we check-in with the Ytepka Society, the secret leaders of Port Nyanzaru, for whom our party has become their most trusted operatives. Our heroes debrief the Society on the various threats to Chult our heroes have uncovered; the predations of a blue dragon at the Phoenix Horn, a fungal infestation called Yumog that may be heading to Fort Beluarian, Red Wizards that have set camp in The Heart of Ubtao, and an incursion of Frost Giants stomping around. Incredibly, they kept their mouth shut about Artus Cimber and did not betray his ring of winter secret to the Society.

Per the Society, envoys will be sent to Fort Belaurian about the Yumog threat. This will result in disaster that our heroes will have to fix eventually. So long as the giants and the dragon keep to the jungle, Port Nyanzaru will leave them alone, but the Society will remain on guard for any movement toward the city. The Society is convinced that the red wizards are involved with the Death Curse and they want to know what our heroes have learned about this Curse on their journey to Mezro.

There isn’t much, but it’s always good to rehash the story so the players don’t get lost. The red wizards are not responsible for the Curse, but they are investigating it and will likely cause problems eventually. The fabled boogeyman, Ras Nsi, or someone pretending to be him, is involved, but is unlikely to be the source of the Curse. He is likely working for whomever is behind this Curse and finding Ras Nsi is the best way to get some real answers. Ras Nsi’s current whereabouts are unknown but we believe that the Oracle of Oralunga may have the answers we seek. We don’t know where Oralunga is either, but legend claims it to be near the banks of the River Tath on the Southern tip of Chult. Our heroes plan to mount an expedition to discover this lost city after dealing with the Pirates. Terrific! We’re all caught up. As to the pirates, the decoy ship is almost ready. Gather your supplies, hire a new guide, prepare yourselves, and rest. You sail in two days.

Of course, there is no rest for the wicked. Instead, our heroes have plans to mess with one of the other Merchant Princes who runs this town. Unfortunately, that Prince also wants to mess with the party and she is way more vindictive about it. There are seven Merchant Princes that run Port Nyanzaru and they all have unique personalities and motivations, but aside from Wakanga there aren’t any specific suggestions to have them interact with the players.

During the course of our adventure, I’ve had a few of them meet our heroes during the homebrewed Trickster Trials of Session 8, then they ran afoul of another when the players started a business selling popcorn which interfered with Prince Kwayothe’s profits. Later, Prince Wakanga was uncovered as a core member of the Ytepka Society and became a valuable ally of our heroes. Finally in Session 25, our heroes were called to a meeting before all the Princes. There they thwarted an assassination attempt by some Yuan-ti spies, but then rekindled the wrath of Prince Kwayothe.

Kwayothe is the most interesting and developed Prince of the group and she should have a larger role in the story. But aside from a petty feud with fellow Prince Zhanthi, she doesn’t do much. She has two succubae as consorts and worships an evil fire god, Kossuth, but doesn’t have any story lines attached to her. Now that she has become the main bad-guy Prince, I gave her all the evil plots of the other Princes.

She is now the Prince that allows the Yuan-ti into the city and informs Ras Nsi of our heroes activities. (In the book, this spy is Prince Ifan Talro’a.) This also gives her a reason why she was missing during that prior assassination attempt. I expanded on her written back story to explain her feud with Prince Zhanthi, whom I made the true target of that assassination attempt.

My Kwayothe grew up a poor street urchin, while Zhanthi was a rich snobby noble and the mother of the jungle guide, Shago;  a favorite NPC of the party. Young Kwayothe fell in love with the beautiful Shago from afar, and the one time that she gathered the courage to speak with him, she was mocked and turned away by his over-bearing bitch of a mother. Kwayothe swore to take revenge, selling her soul, rising up through the ranks, and is now a Merchant Prince whose only goal is to tear down the nobility and destroy Zhanthi. For her part, Zhanthi doesn’t even remember the incident nor recognize Kwayothe.

Back in Session 27, I ran a one-shot adventure (thanks Villains & Minions) that trapped my players in an abandoned mine infected with deadly hallucinogenic spores. At the end of that dungeon, one of the random treasures was “an embarrassing love letter written by some noble” to be selected by the DM. I made that letter (now a diary) be from Kwayothe. I’ve included a PDF of this diary that you can view here: ToA Kwayothe Diary. How this letter came to be here in this random mine made no sense, (a thief stole it, hid in the mines, and was killed by the spores), but my players didn’t care. They now had something that they could use to screw with this petty Prince that once pissed them off. Yes, most player-directed plot lines are based purely on spite. Little did they know that Kwayothe already had an even more dastardly plan for my player. But before I get to that, I gotta split them up.

By design, players are very lethal as a group. With all the multi-attacks, bonus actions, actions surges and reactions, a group of 4 players can have up to 12 actions or even more per round. Meanwhile, a group of four goblins gets one attack each and the occasional Disengage. Goblins suck! Since many bonus actions and reactions are triggered by a different player, it is imperative for the party to stick together and have each other’s back. This is why we DMs have to constantly throw more and more bad guys at the group, or wait for one player to go off their own to ambush them. Usually, this occurs when the thief or ranger goes ahead and scouts a new area. Sadly, fighters and wizards never seem to leave each other’s side; a pathetic co-dependency if you ask me. But there is one useful and unsuspecting time when every player splits from the party to do their own thing. Downtime.

Tomb of Annihilation does not lend itself to having much downtime. The time pressure of the Death Curse means that any free time in Port is spent planning the next expedition and heading right back into the jungle. That doesn’t leave much time for carousing, gambling, building that wizard’s tower, or robbing every peasant of the 6 coppers hidden under his mattress. But today is different. Today, our heroes have 48 hours before the next mission begins, so I ask each player what they want to do. I also ask them to roll a d20, but I don’t tell what it is for.

Thames wants to go back to the Temple of Savras to conduct more research on Chult and Ras Nsi. Off he went, blindly to the slaughter. Martic wanted to purchase a new set of manacles, which will prove useful in the next session and for restraining possessed players much further on. Off to market he went on his solo adventure. Gwen wanted to enjoy a stress relieving bath at the bathhouse (yes, this was a thing with her character). But before she got there, she met her own fate at the hands of a suspicious stranger. Since Theo missed today’s adventure, his character Roland headed off to watch the gladiators in the coliseum and had his date with destiny off screen.

Little did our heroes know that they were all being stalked. After they got to their destinations, they each had an encounter with some nefarious rogues who had no desire to roleplay, just murder. Each player faced off against two assassins who struck without warning and a third who remained cloaked and removed from the battle. The most interesting element of this encounter was to watch how each player handled the same scenario. This is why I love D&D so much. There are infinite choices to every encounter; some are better than others, and some are downright terrible, but even the bad ones can lead to new and unexpected developments. This is why I love hearing about how other campaigns play through the same adventures. The new ideas, creative solutions, and subtle nuances are fascinating to me.

Thames’ encounter took place in a library and I expected the dragonborn scientist to show a little restraint amongst all the fragile scrolls and rare tomes. Nope. Thames went super nova with every breath weapon and area effect spell at his disposal. This is a common lament of town encounters where the player can go all-out with their abilities and simply take a long rest right after. Thames obliterated his enemies and when he was done, this wing of the library was in shambles; some shelves were on fire, an entire rack of scrolls was frozen in ice and currently melting into useless soggy parchment, and the whole area was covered in broken glass from the blasted windows. The temple acolytes were appalled at the destruction but terrified to accost the clearly dangerous dragonborn. They begged him to just leave and not hurt them. I intended this to be a whole thing where Thames gets banned from the temple, (you know, consequences) but as we will soon learn, this is the last time our heroes will ever be in Port Nyanzaru, so I never got to teach Thames a lesson about treating the world as if it were real. (You know, verisimilitude).

Meanwhile, Martic was in the Grand Souk, the Port’s marketplace, but before he could buy anything, he was accosted by a gorgeous courtesan. “My, my. You are a strapping, handsome lad. How about you buy a girl a drink and we can get to know each other a little better?” Martic wanted nothing to do with this distraction and brushed her off. “Suit yourself,” she said as she slunk back into the crowd. She was barely out of sight when Martic was attacked by his assassins.

Martic obliterated the first assassins with some lucky crits, forcing the hooded agent to unveil himself early. When he threw back his cloak, he revealed that he was in fact a bearded devil. This was a surprise for my players since demons and devils do not play any real role in the adventure and they are not listed as allies of Kwayothe. But I felt that it elevated her character and gave her a greater sense of menace. I hoped that this would open up a potential storyline involving the Cult of Kossuth. But my players never dwelt on it and it never became part of the story. They just looked at the devils as another monster to murder and move on.

Mean-meanwhile, before heading to the spa, Gwen wanted to check out the community water well that was pivotal to the Yuan-ti caused plague from Session 21. So, that’s where I staged her ambush. As the least combat capable character, I knew she would have the toughest time with this encounter, but she did okay. She took out one of the goons, but then was in a spot of trouble when the bearded devil joined the fight. Fortunately, she owns a mace of disruption which is very useful versus fiends, but was unfortunately cancelled out by her abysmal strength. Fear not, I had a backup plan to help her out.

So here’s how I ran this three-sided encounter. I set up each scene, one at a time, with every player at the table waiting their turn. I kept the descriptions brief so that each player didn’t have to wait long. Once combat was about to begin, I put that player on hold until each one caught up. Once all three were fighting, we rolled initiative, and we played out each round in that order. All the bad guys acted on the same initiative count against their individual hero. When Martic killed his first assassin early (BTW, I used the veteran stat block for these rogues), I put that combat on hold until the other players caught up. Then I revealed the bearded devil surprise and played out the rest of the battle.

Gwen was having a hard time with her bearded devil, (not through any bad strategy, just bad dice rolls), when suddenly the most handsome Chultan male ran onto the scene and turned the tide of battle. Together the two were able to dispatch the remaining assassins. After the battle, Gwen thanked her savior. “No thanks are necessary my lady. My reward is in saving a beautiful maiden such as yourself from the hands of this despicable rabble. The favor of Ubtao is upon you that I happened to be in this district visiting my Baba (grandmother). But where are my manners? My name is Indar. I work as a guard at the Temple of Sune and if you truly wish to repay me, then you will permit me to buy you a tankard of tej (Chultan mead).” Cut to Martic.

Martic was cutting through his assassin like a hot knife through butter. When the devil revealed himself, Martic murdered him in two rounds. Usually, I don’t bother with morale. Once a battle begins, it’s a fight to the finish. Occasionally, I might have an enemy surrender. Especially, if the enemy is weak-willed and the players need to gain some information through interrogation. But sometimes, especially after a player shows a particular lethality, I’ll have an enemy make a 50/50 morale check. Above 10, he stays. 10 and below, he runs. Martic’s final assassin just witnessed the massacre of his boss, and he ran. Martic chased after him. Pause here and cut to Thames.

Now here is my true purpose of splitting these guys up: Kwayothe’s succubae. Out of game, my players know that Roland was once charmed by one, but they don’t know about the other. So this time, some other players will get the “fun” of meeting these guys. But, who to target? This is actually a delicate question. The succubae whole gimmick is using sex as a weapon, but not every player is down with that. In my group, Wes has zero desire to engage with any content with romantic overtones, so I won’t use him. That leaves Ian, for whom I’ve yet to find a roleplay boundary, and James, who is down for almost anything but is only 16 and my son, so I don’t want to make it creepy. Too late, Dad!

Early on, I had each player roll that mystery d20. This was for the Wisdom save against the succubus charm that was occurring now. I could have had them roll this save at the moment the charm is placed. But if I suddenly have players rolling saves in the middle of a conversation, then they will know that something is going on and act differently. It’s the same when you ask the group for a Perception check and everyone fails, and is now convinced that there is something vital in the room that they need to find. By rolling the save out of context, if the character is charmed, then she will be informed that she is charmed at the right time. But if the character makes his save, then the encounter will proceed without disruption, blissfully unaware that they were almost enslaved. Bear in mind, this trick should be used sparingly, especially when it involves removing a player’s agency.

As it was, Gwen failed her save but Martic and Thames passed. Even though Thames was never a target, I had him roll this mystery roll to avert suspicion. For his post combat scene, Thames played out the tense conversation with the shocked scribes as they tried to kick him put of the temple. I used his mystery roll as his persuasion attempt on the clerics to not call the guards on him. He was just happy to not get arrested. Again. Similarly, Martic was not charmed by his courtesan, whom he promptly ignored. He could have willingly engaged in conversation, but chose not to, which is perfectly fine. Instead Martic attempted to follow the fleeing assassin to his hideout. This led him into the wealthy section of town where all the merchant princes live. Very suspicious.

For Gwen, she failed her roll and something must have snapped inside this poor sheltered cleric, as she unleashed all her inhibitions. To the point where even the incubus (and Wes) was uncomfortable and began looking for any excuse to extract himself from the encounter. “By the gods, do you kiss your mother with that mouth? My lady, I would love to stay and explore all these things you suggest, but oh my, would you look at the time. I must be going. But please come to my villa. It’s the yellow one with the red windows next to Goldenthrone. You can’t miss it. See you soon, my love.” Indar beat a hasty retreat, but I did not release the charm. The real goal here is that when combat eventually ensues as I expect, Gwen will be at the mercy of this devious devil. For a few rounds at least. By the way, no one other than Ian knew that she was charmed and they thought that Gwen was just being obnoxiously infatuated with this guy.

Back to Martic, hot on the heels of his quarry. He bumps into Thames getting tossed out onto the street in a huff. “Quick, come with me. I’m tailing the guy who tried to kill me.” “That’s peculiar. Some ruffians just tried to assassinate me too!” “This is no time for your big-words dragon chatter, I’m stalking a killer. Let’s go!” They continued to follow the thug who led them to a lovely villa next to Goldenthrone. A lovely yellow villa with red windows. They were joined shortly by Gwen, who managed to find Roland off-screen and bring him along for her date with her mysterious new boyfriend. The party was back together and began making plans to infiltrate this mansion.

It was no secret among my group, that this was Kwayothe’s villa, especially when Martic cast locate object, using the diary fragment and learned that the rest of it was inside. I had planned for the group to sneak into this mansion, uncover her secret devil worship and Ras Nsi alliance, confront her, and kill her, ending the Yuan-ti connection once and for all. The diary fragment was only intended to spur the player’s interest in Kwayothe, but they decided to make the diary to whole point of the mission. I learned afterwards that they were afraid to confront her directly, expecting Kwayothe to use her political influence to have them run out of town or executed. It’s my own fault really. After so many encounters where powerful NPCs refused to tolerate their obnoxious player attitude, now when I give them the opportunity to take one out, they refuse to do it.

Instead, the party elects to send one player, Martic, on a solo stealth mission, with the singular purpose to find the rest of that diary hoping it has all the guilty confessions needed to bring Kwayothe down in an exciting court trial. This ain’t Law & Order detective, it’s D&D; now get in there and kick that traitor’s ass! Even worse, the diary is just the musing of a 12-year-old girl, the real evidence is in a different room. In hindsight, I could have moved the diary to a spot in the house that would compel a confrontation, but that seemed unfair, since three members are standing outside, not adventuring.

The whole thing just didn’t turn out as I planned. I kept hoping that the rest of the group would enter the villa but they were determined to stay outside. As it was, Martic did as good a job as you would expect. I’d hoped that Martic’s secret past as a thief would provide some interesting role-play, but no one questioned his new-found rogue abilities and nothing came of it. Casing the joint, Martic saw two guards at the front entrance. He tried to climb a tree to reach an upper balcony but fell and had some tense moments when Kwayothe opened the very doors he was about to use. These doors led to her bedroom, and a major fight, so Martic gave up on this way in.

Martic found a back door and snuck in just before a guard came around the corner. Following his locate object sense, he came upon the sauna and royal bath but no people and no diary. I kept up the tension by describing all the sounds of people moving about upstairs and voices of guards approaching on rounds. The bath may be a dead end, but the Sense is telling him to continue south to find the diary, so he’ll have to find another way. Daring to exit out to the main atrium, he finds a passage leading south that leads to a kitchen and three surprised servants. He also failed a stealth roll, and hears a guard tell another to “check out that noise.”

With no time to lose, Martic failed the campaign’s only Intimidation check, telling the cooks to “Stay quiet, or I’ll kill ya!” They screamed for the guards. Luckily with his off-hand attack, Martic gets three attacks per round. Whack, whack, whack, three cooks are now unconscious but a precious six seconds have elapsed. Martic quickly barricaded the door with a table and ransacked the kitchen. After several excruciating long seconds of fruitless searching, Martic found the remnants to Kwayothe’s diary burnt to ashes in the central fireplace. I told them the diary wasn’t what they were looking for. Later, the group rationalized that when part of her diary was stolen, Kwayothe destroyed the rest before it could fall into the wrong hands. But there was no time to consider this now. Armed guards were trying to force their way into the kitchen!

There were no windows in this kitchen and the other doors only led to closets. As his only option, Martic ran up a narrow staircase that opened into a laundry. There was a door that leads elsewhere into the house and a single narrow window. Just then the guards burst into the kitchen and by now the whole house was aggroed. With no time to spare, Martic smashed out the glass, scrambled across the terra-cotta roof, jumped to the ground below and ran, with his perplexed conspirators following quickly behind. This break-in was a bust.

I was bummed. I had all sorts of encounters planned here. Of course, there was Kwayothe herself as the only cleric-based villain in the game with some cool, fire-based spells to battle against Gwen. Plus, there were the succubae, a bone devil, the Yuan-ti mage that escaped our heroes earlier, and a trapped fire elemental that would probably end up burning the house down. There was some neat treasure, with some thematic artwork to steal, and some nice magic items. But I wasn’t too worried. I’ll just save this for another day. I always figured we would come back and properly conclude this Merchant Prince saga. Had I only known…

Our heroes didn’t want to push their luck and beat a hasty retreat to Meepo’s animal shelter. I didn’t want to beat a dead horse and didn’t have any of Kwayothe’s goons come after them. Besides in the morning, they got to hire a new guide and I got some plans to wrap up yet another loose end with yet another annoying NPC, actually two: Faroul and Gondolo.

These guys have been a perennial thorn in the side ever since our heroes rescued them from the Yuan-ti slavers back in Session 13. They have managed to claim credit for every heroic deed performed by the real heroes, our players. They may be terrible guides, but they have great PR. Who rescued those kidnapped citizens? Faroul and Gondolo. Who cured the Yuan-ti plague? Faroul and Gondolo. Who averted the assassination attempt in Goldenthrone, despite being no where near there? Faroul and Gondolo. My players hate these guys more than Ras Nsi.

I wanted to run a fun little scene where our heroes can finally confront these two thunder-stealing charlatans. If they can catch them. For as soon as they see our heroes coming, Faroul and Gondolo will take off, leading to a merry little chase through the streets of Port Nyanzaru. Tomb of Annihilation does not have a chase scenario and the 5^th edition rules are very wonky, but I love a good pursuit and I really wanted to have one. I ran a successful chase in Waterdeep: Dragon Heist – Session 17 and designed a CHASE Tracking Sheet for that encounter that you can use in your game. For Tomb, I created a custom list of complications to throw at my players.

And then I didn’t use any of it. The botched robbery of the Merchant Prince villa took way longer than I expected, and this intended chase would just be a distraction from what must happen before next session, the hiring of a new guide. So Faroul and Gondolo live to pester our heroes another day, and we’ll just have a roleplay encounter with the guides who remain.

The pickings are slim. Faroul and Gondolo are in hiding. The tabaxis River Mist and Flask of Wine were used before and got lost so much that we won’t use them again. Qawasha, Musharib, and Shago are unavailable in Fort Belaurian (and getting infected by Yumog), so they’re out. That leaves the one-armed and crazy dwarf, Hew Hackingstone; the notoriously unlucky lycanthrope, Azaka; the sarcastic shit-talker. Salida; and the here-to-fore unseen guide, Eku.

I have deliberately left Eku out of the list of guide options, because she is problematic for beginning excursions. *SPOILER ALERT*. Secretly Eku is a couatl in disguise and can lead the players directly to the end of the adventure if she so chooses. The couatl is a sacred animal in Chultan culture, as one named Ecatzin worked along side the god Ubtao to create the Chult we know today. I mentioned this favored couatl ages ago in Session 12 but I haven’t had the opportunity to bring it up since. As for Eku, she knows the location of every secret location including Omu, and if she joins the party too soon, you may be compelled to skip all the cool jungle stuff and head straight to the Tomb.

But for us, a mere year and a half into this campaign, it finally seems okay to let this weird feathered-winged-snake-lady into the story. Unfortunately, her obsession with finding “heroes of good moral fiber to defeat the “scourge” plaguing our beloved Chult” came on a little too strong for our heroes and they passed on using her. She replied, “Such a shame. When you are prepared to accept your destiny, I’ll be here.” Ain’t gonna happen, lady. Our heroes also passed on Azaka, who proved a liability in combat during their brief stint with her in Session 31. She’s actually a formidable fighter who just had some dismal dice roll, but too bad, she’s out. They also passed of the batty dwarf. I could never get a grasp on these dwarves and never found a way to make them memorable, so he’s out.

This left them with only one real choice, Salida. Her no nonsense trash-talking and mockery of all the other guides really made her memorable. She also thinks that Faroul and Gondolo are incompetent idiots, which endeared her to the players. “See, Salida gets it. Why can’t everyone else see what clowns those two guys are? I like her. We should bring her along.” Yes, yes you should. Bwah hah hah. She will *SPOILER ALERT* betray the party, since she is also an agent of Ras Nsi, so I got that to look forward to. But before that, we got pirates to pillage. So, with our new guide, new equipment, and a new boat, the blink and you’ll miss it on page 21 Brazen Pegasus, our heroes are finally ready to enter Act 3 of our little drama.

Next week, we bid farewell forever to Port Nyanzaru as we face off against pirates, typhoons, hydras, and Star Wars battle droids?!

As always, store any and all skipped encounters in your “To harass my players later” folder and Game On!

A successful book is not made of what is in it, but of what is left out – Mark Twain

Don’t forget to check out my Tomb of Annihilation Resources Page, filled with all the stuff I use to make this epic campaign even more epicier: My full Campaign Diary, plus Handouts, Maps, Charts, PDFs, Images, and more to use, abuse, or ignore at your peril.

And written specifically for this adventure, read my Explorer’s Guide to Chult to delve into all the legands, lore, history, religion, and culture that I used to bring even more life to this adventure.