Skull & Shackles - Pathfinder 2e Conversion
There's adventure to be had on the high seas when a group of press-ganged strangers seizes a ship and becomes embroiled in the plots and politics of the Shackles—an infamous island chain dominated by pirate warlords. But as these new swashbucklers make names for themselves, rival scalawags, enemy navies, legendary sea monsters, and the infamous Hurricane King himself seek to see them walk the plank. Who will survive when there's glory to plunder?
There comes a time when your typical fantasy adventure isn’t enough. Sometimes you just want the freedom to be evil, to sail a ship across the seven seas, and steal plunder (and maybe even make a cryptic map detailing where you hid said plunder). May I introduce Paizo’s Skull & Shackles adventure path!
This adventure has everything you could ever want out of a pirates campaign. Naval combat, rubbing sabers with pirate kings, being press-ganged, saying ‘arr’ way too many times, and taking on an armada of warships with your trusty ship, your favorite cannon, and staunch allies.
About a year ago, I finished running a (modified) Skull & Shackles campaign for my players. While it was modified, to better fit my world and the story I wanted to tell, I kept around 50% as is for a strong and sturdy backbone for the campaign. Of course, at the time, there was no conversion for this adventure, so I also had to convert it. And make naval combat rules. And update plunder rules. And create dozens of monsters, traps, magic items, and more for me to run it for my table.
If you want my thoughts on the adventure and the conversion, keep reading. If you just want the conversion, click the link below.
Just an important note: this conversion was created to be used with Pathfinder 2nd edition. A conversion still relies on the original adventure created by Paizo to be run. Get Skull & Shackles on Paizo to run the adventure.
We’re Pirates?
The opening to this adventure begins with the players waking up in a ship’s hold, held captive by pirates. They are informed they have been press-ganged, and they have two options. Become pirates or become shark food.
Now, obviously, players should’ve made characters that want to be pirates—but not everyone gets that memo. I only had one character who was even good at swimming or sailing out of 6 characters. While mechanically it isn’t a good start, it is narratively so I guess I can forgive them on that part. Sometimes you don’t choose the sailing life, the sailing life chooses you.
Naval Rules
The biggest challenge with a conversion like this are the subsystems that come with it. I needed to create a pretty fleshed out naval combat system that could emphasize the players getting stronger, better ships, better weapons, and more.
To that end, I took inspiration from Starfinder, Dungeons & Dragons 5th edition, Pathfinder 1st edition, as well as systems like 7th Sea and other pirate-focused games (shout-out: Assassin’s Creed Black Flag). I wanted the system to mirror Pathfinder 2e progression, where you add your level to your proficiency, and to encourage players to interact with naval combat with a theme.
To that end, I created three types of upgrades you could have for your ship: Mobility, Offense, and Defense. Offense and Defense are pretty self-explanatory, whichever one you choose, you’ll become Legendary in that specific area of focus. As for Mobility, that was inspired by actual pirates who valued speed above all else. They wanted to get in close, board a ship, and then be gone as fast as possible. They would often hide behind islands and shoot out with their highly mobile ships before their targets could get a chance to flee.
From there, I developed rules on movement, facing, travel speed, actions in combat, and more. A big focus, and one that I still want to do more with, is giving players who aren’t the pilot something to do on the ship during naval combat. It’s easy for the pilot to be excited by naval combat, they are maneuvering the ship and trying to ram other vehicles, it’s less interactive for the players who are on a wild ride.
Luckily, being on the deck of a pirate ship gives one way more options than in Starfinder where you can’t really crack open a window on your spaceship and shoot your pistol at the enemy. While on a deck, players could still lob fireballs or even swing from ropes and try to land on the opposing ship. That said, I created multiple roles that would help aid their ship, as well as created unique actions that they could take during naval combat to help keep them invested in the game.
Was I wholly successful? Depends on the naval combat and the player. I definitely made it more interesting for them, but I still want to keep adding to it and really help them be as invested as the pilot is. Of course, the player has to come excited for naval combat or else it doesn’t matter what actions or abilities I give them, they just won’t find it fun.
But You’re Not A Pirate!?
In this adventure, you fight a lot of humanoids (no surprise), as well as beasts, aberrations, other pirates, sahuagin, and…. cyclops? Well that’s a weird addition. While it makes (some) sense in the context of Golarion’s lore to fight cyclops, it did feel weird in my pirate adventure.
This was one of the big deviations I made from the book. Instead of just fighting cyclop after cyclop, I decided to instead change Book 4 from cyclop-island, to giants-worshipping-a-primordial-and-attempting-to-unleash-it island. Doesn’t roll off the tongue as well, but I thought it did a better job at giving the players more interesting monsters to face (I had different types of giants plus elementals), and I could introduce some of my world’s lore and get them worried.
See, one of the players had made a deal with a different primordial and became a skeleton. They had a vested interest in the primordial they served, and definitely didn’t want to see a different primordial be unleashed while the one they served remained imprisoned. I added in more elementals because they were one with the elements (serving a primordial and being genie-kin), which gave the players something more different to deal with than normal pirate shenanigans and cyclops.
In my opinion, book 4 is the weakest in the series and if I were to re-run the campaign, I’d pry ignore the 4th book entirely and have them go on a wild treasure hunt, like in Pirates of the Caribbean: Dead Man’s Chest, for a more cohesive story. That said, it does give the players a ‘home base’ but to be honest… they kind of already had one from a previous adventure when they took over a fort and renamed it after one of their characters.
If players want a home base, they’ll make one, steal one, or threaten you enough with fireballs that you give them one. I don’t think you need to just hand one over that they have no real connection too.
Monsters
The next biggest challenge in converting an adventure are the encounters. You want to stay true to the original intent of the adventure and the writer, while still making sure you follow the new system’s rules and guidelines.
If the original adventure calls for 12 grindylows to attack the party, and in that edition the encounter math says that that is a moderate fight, but in the new system, 12 grindylows would be beyond lethal, you gotta find the balance between them. You still want an onslaught of grindylows, to stay true to the intent of the encounter, but to keep to the balance of your new system and reduce that number to 6 or 7 grindylows. It’s still a lot of terrible goblin-octopus monsters, but now your players have a fighting chance.
After going encounter-by-encounter through the series and working out the encounters, you then have to build any new monsters you might need. Unique NPCs will need to be created, monsters that just don’t have an official version in the new system need to be created, and also monsters that are already created need to be re-created cause they are the wrong level in the official sources.
All told, I created 55 stat blocks for the adventure, with an extra 7 stat blocks because I wanted to expand my piratical adventure. The biggest challenge I encountered was trying to match flavor to mechanics. In the adventure, if the NPC is a master conjurer, sure you could cheap out and just make a wizard with a few conjuration spells, but that isn’t very interesting (especially when you have three wizards back-to-back-to-back that the party must fight).
To that end, I had to think of ways to utilize the mechanics and make interesting NPCs and create fun abilities for monsters to have. Pathfinder 2e doesn’t suffer the same problem that Dungeons & Dragons 5e has. It’s monsters are interesting to run and aren’t just claw-claw-bite every round.
Which makes them awesome to run, but not as awesome to create. You have to think of fun and interesting mechanics they might have in an encounter. Typically, the way I go about doing that (even in 5e) is by imagining a fight against such a monster in my head. How does the monster move? How does it fight? Is it scary? Does it climb to the ceiling or lob orbs of magic? How does it strike out at adventurers? How does it deal with multiple people at once?
Monsters should tell a story when you fight them, and players should quickly understand the encounter role a monster has within a round or two (brute, skirmisher, lurker, etc). If your players can’t remember what made a monster unique after the encounter is over, then it’s probably because your monster is boring and failed to have much of an impact on the table beyond being a sack of hit point meat.
Pirates Against the Armada
The closing book of this adventure has the party facing off against a naval armada with powerful ships, powerful captains, and a big pirate choice. Will you bend the knee to the cowardly pirate king, or become the new pirate king?
Of course, the choice is obvious. Time to take the driftwood throne and claim rule over pirates (what could go wrong besides your rule being brutally ended by some upstart pirates?). My party handled the armada battle pretty well, their ships obliterating their enemies and turning enemy ships into splinters and driftwood. However, once the armada was destroyed, they decided to destroy the pirate king—which turned out to be way harder than they first guessed.
They thought the pirate king had grown soft from drink and sitting on a throne all day. What they didn’t realize was that apparently the pirate king shoots better when they’ve been drinking all day as the wizard went from full hit points to almost permanently dead in a single shot (sneak attack is dangerous on a critical hit, along with the firearm’s fatal trait).
It was a nail-biting final fight, there was ebbs and flows, but somehow the party landed the final blow on the pirate king and took their rightful place on the throne. However, six butt cheeks on the throne at one time makes the throne feel pretty small, no matter how big the seat is. While they promise to work together, I can only imagine that if we flash forward a dozen years in the story, outright civil war would break out across the various pirate factions as each fought to be the sole ruler.
Loot
Pathfinder has a very nice, fleshed out loot and reward system. It makes it easy to know when you should be awarding magical items and how much.
Of course, that means when converting an adventure, you need to be careful. Different systems don’t agree on the value of a gold piece and it can be tempting to simply say that every gold piece in the old system is worth a silver piece in the new system (or vice versa). Never have I ever felt closer to an accountant than when I was going through, counting up the loot, and carefully re-distributing loot in the new system. It almost felt like paying taxes, but you actually enjoyed paying taxes. …Maybe not the best example I could’ve picked.
When creating or assigning loot, the most important thing to me (beyond making sure it aligned with the party’s wealth level) is that it fits in thematically. If the book says that the party finds a ring that casts a specific spell, but you find a hat that does the same thing in the new system, go ahead and swap them out. I have no problem switching out a ring for a hat—so long as that ring isn’t important (like a medusa looking for rings to add to their collection) and you keep it flavorfully the same.
I think loot is a slippery slope you can find yourself diving way too deep in. If a creature wears a ring of natural armor +1, you’ll drive yourself insane trying to figure out how to transfer the mechanics of that ring into a new system which doesn’t support those types of mechanics. Instead, you just create a ring of mage armor and call it good enough for your purpose. It doesn’t do the same mechanical thing, but what it does is convey the theme of what that ring should do. It protects the wearer through magic.
And that’s true for anything.
Thematic beats specific mechanical elements. So long as you remain on theme when converting an adventure, you can pretty much ignore mechanics. You want the players to walk away from the adventure, not caring if the magical cloak they found does a specific thing, but rather how it fits into the adventure as a whole. People won’t remember specifics, but they will remember how the adventure made them feel and what themes they interacted with.
Pirate’s Life For Me
After spending a little less than 2 years running this campaign, even with me modifying large chunks of it to better fit my table and what I wanted out of a pirate game, I can highly recommend this adventure. It’s a fun and unique way of playing a high fantasy game.
If you’re looking to run Pathfinder 2e and want something that isn’t just another fantasy adventure, Skull & Shackles can scratch that itch—so long as you aren’t afraid of jumping in to the deep end and fighting a shark with your bare fists.
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