The Southern Isles are in the location that The Pirates Isles are in vanilla DnD, I just thought the original name was lame. I have used some of the original lore for some of the islands, but mostly it’s my own stuff. That means the surrounding powers are Sembia, Turmish, These, Aglarond, etc. Yo be honest I’ve not put a lot of research into those. The Isles attract a sorts of folk from all sorts of places.

The Southern Islands Company are a proxy for the Turmish government, and it is them who patrol the islands looking for pirates.

The most famous pirate hunter is probably Commadore Roger Todgeson. He has a long standing enmity with Captain Verse, a pirate captain who has the lofty goal of ousting the Company and starting a pirate republic. Currently he is on his way to Thatch, a town in the Western region, and the place most newcomers to the Isles make landfall The party are also on their way there. Captain Verse feels it is time to try and liberate the town and has asked the party to come to his aid. The Company sense unrest is afoot and have call s Commadore Todgeson to help sure up their forces. The party and their crew, along with Verse and his own crew, will try to take the town before he arrives, and then defend it on e he does.

The last pirate to be caught and killed… hm… I’ll say that would be Captain Jack Chaffinch. He was taking a prize out East when he ran into Todgeson’s ship. They fought valiantly but were overwhelmed and when Todgeson arrives at Thatch he’ll hang him up in the Harbour as a warning nitnto resist him. Chaffinch’s ship sails with Todgeson, having been captured. Could they take the ship back ? Apparently he’d managed to take a Theskian treasure galleon before being caught himself. Could be the gold is still in its hold, just waiting for greedy pirates hands to reclaim it!

In terms if crew positions, mine might not be the most realistic but are designed to give the players interesting roles and ways to effect things.

The Captain - gives orders, makes in-the-moment tactical decisions

The Quartermaster - in charge of the crew and keeping them fed and watered, in charge of rum rationing as well

Lookout - doesn’t seem like much, but if you put a PC with high perception in that role, you’ll spot stiff better

Cook - has a big effect on the morale of the crew

Shantyman - perfect role for a bard. Also has a big effect on morale and can inspire great feats from the crew with performance checks.

Bosun - in charge of maintaining the ship, when repairs are needed, etc.

There is a pirate code that they are expected to follow. Captain Verse insisted on this when he helped the players take their ship. Its quite long but the big points are:

• All booty must be shared equally, with tge Captain and the officers getting two shares each.
• All major decisions must be decided by vote (such as whether to take a prize, where to burn a ship or take it…). The crew may even vote out their captain if they dislike how the ship is run (although in practice I’d likely just do a good old mutiny).
• No one may steal from another member of the crew, on pain of being marooned, keelhauled, or killed.
• No murdering each other, although fights are tolerated within reason. If they get really bad they must be settled ashore.
• you can’t leave the rew until you’ve at least helped the make a prize.
• No freeloading, everyone pulls their weight

Generally the pirates work together, and if there was a local pirate leader that would be Captain Verse. Some go rogue or shun the pirate code, like the BBEG pirate captain Blackfin, who’s crew are mostly undead and who has no allegiance other than to his Demon Lord, Orcus. Verse has done a great job of uniting at least rhe pirates in the Western regions of the Isles, and hopes to lead an uprising against The Company and start a pirate republic.

Burial at sea mostly would e standard, with a ceremony where they take turns speaking about the deceased and moments from their time together. Or they would try to emulate the traditions of the individual’s culture. Pirate crews are made up of all sorts of folk from all sorts of places, so they are a melting pot of different traditions.

These are great questions!

“There’s an island to the North, right? Surrounded by a maze of coral reefsit is. No one has been able to find a path to it, even by rowboat, but folk have been dashed on em even taking it careful like. Sailors swear they saw the foral move! BUT my mate Ron, he said he heard off his mate Jim, that there was this druid on his ship what wildshaped into a pelican, right, and flew over it. Said there was some kind of temple or shrine in the middle of it. But he couldn’t get close. This deafening voice booming in his head, saying he had to pass the test and find the way there! Couldn’t resist the voice he said. Had to donas it says like it was pulling his strings! Now, I reckon, if there’s a test, there’s a prize! I bet it’s treasure!”

There’s rumours of a kraken, of course. But it could just be ships lost to pirates, or sunk in storms, or taken over by the sahuagin…

Speaking of the sahuagin, they have been a lot more active lately, there attacks more frequent and more organised than before.

There’s a rumour that the dread pirate Blackfin has been killing while ships of people just to turn em all the zombies. He’s building an undead armada! He’s friend to none, pirate or civvy!

As for superstitions, they’re sailors, so they are a very superstitious bunch. One of my party killed an albatross, and the crew were going spare at the bad luck. They made him wear it round his neck as penance for the bad juju, and the ship was becalmed for days, drifting with no wind. The players tried all sorts to lift the curse but it was actually an encounter I found on reddit one time, the Sinister Seagull. It takes the wind from a ship’s sails and can mind control the crew. They spotted one of their crew throwing gems to the seagulls and had to have a battle with it. They couldn’t tell which was the evil one son they were blasting every seagull they could see. Ingrave the Sinister Seagull basically every non lethal psychic spell I could find and had fun casting confusion, crown of thorns, power word pain, etc, on the party. They took very little damage and it was a frustrating fight for them, but when they finally exploded the right seagull, they were very releived

The Southern Islands Company (SIC) is basically a stand in for the East India Company. They wear red coats and speak with posh English accents, and are basically a private army, owned by a merchant company, who in turn operate with the blessing of their home government. They are a human colonial force. There are developed towns with a merchant class, who do quite well, and an underclass made up of pirates, other races and the indigenous people of each island. The Company takes a cut of all the food that, is grown, and have recently begun increasing their cut to the point that the underclass are going hungry (and getting angry). The indigenous people are treated the worst, some sold into slavery others just worked like slaves.

The local pirates stand in opposition to them and its mostly SIC affiliated merchants who get raided. The SIC do their best to hunt down the pirates, but they are spread quite thin, particularly in the Western parts of the Isles.

There is a black market run by the pirates to sell their booty, and a lot of the goods end up back in the hands of the company, either trough seizure or through the more corruptible Company men.

I have cannons in the setting, just cos I wanted the players to be able to use them, cos fun! I’ve developed a way of doing ship-to-ship combat that has been working quite well.

I balance the encounter with a manageable number of enemies to match the party, and maybe one or two named NPCs. They battle it out while the two crews fight around them. The crews go in with a set strength rating that translates to a modifier. At the start if each round, both crews roll a d20 and the loser takes one away from their modifier. I determines the starting mod for the players by assessing morale if the crew, how well fed and we’ll armed they are, etc. I use the results to add flavour to the battle. So it’s like the party are fighting some of the crew, but I’m simulating a larger battle around them. If their crew is losing, the PC cam use their actions to affect the larger battle and swing it back in their favour.

Each turn, each ship can move its movement speed and fire cannons/ballet’s on either side. The players can use their actions to do these things or, if they have enough crew left, they can give orders to have them do it.

Makes are still very useful aboard ships cos they can do stuff like create a gust of wind for a burst of speed, or create a fog cloud for visual cover. Also fireballs!

well, since its in the Forgotten Realms settings, access to cannons are rare and limited - and really expensive - where a small island of a weird gnome sect in the far south west of the continent hold the monopoly to guns and cannons. Mostly, mages and other magical users would be employed to either power the sails and/or defend from attacks.

as for the maneuvering part, one can roleplay a ship chase, running mages dry, and then the more powerful ship has the chance to get away or attack the remaining fighting crew as one would. And since a ship will fight for its very existence, unless the opponent are slavers, every man will fight, which shouldn’t be fought out unless you group all combatants into one “group” and roll for them to see how they are doing.

More ideas:

• Slavers are a topic in such games. One could think about the wealth distribution among the crew, among certain factions, regions, and flesh out the region accordingly.
• Check the campaign guide for trades countries would ship overseas, what items could they want to smuggle?
• What kind of taboos exist on land, which your crew might flee from and become Privateers?
• How are Pirates supplied?
• Where is their landing port, safe haven? How is it defended when the main part of the fleet is gone? Access to repairs? How do they recruit additional crew?
• What enemies are there? What “Kingpins” of the Underworld (can also be intelligent Monsters) exist, what foes? (how a about a beholder “kraken”?)
• How are the landlubbers acting towards the crew, what kind of people are there? Do you have primitives, voodoo shamans and a carribbean setting or do you prefer the privateer British setting, with more refinements and fortified towns - or something in between?

Source: FR Campaign Guide & Drizzt Books

notable mentions to check out:

• (TSR/2nd ED): Pirates of the Fallen Stars
• (D20): Corsair the definitive Guide to Ships / Gareth-Michael Skarka

There are tales of buried treasure, maps with a marked ‘X’, etc. But currently there is a greater prize which some of the crews and functions are frantically searching for. One particularly viscous and evil pirate captains, a sharkman necromancer named Blackfin who, along with the Southern Islands Company itself, is one of the BBEGs of the campaign. He is in the employ of the demon Lord Orcus.

You see, a great hero stole the Wand of Orcus, and then was lost while passing through the Isles. Blackfin has been promised great power if he retrieves it for his master, so he is raising an undead army to find it. He’s also made an alliance with the sahuagin, a local population of aquatic arseholes.

Signature dru k would of course be rum! Particularly spiced run, sometimes mixed with ginger beer and lime (which is a real cocktail called a Dark & Stormy)

Sade havens… there’s the idland of Oresk, on which is the hidden treetop hideout of thw pirate queen Anne Bonny. She’s beautiful and ferocious, and most of her crew are in love with her. There’s also Tortuga, a town built onto the back of a great Zaratan (giant turtle). The zaratan makes them powerful, so the SIC have not been able to bully them into economic submissions like other places. The players managed to convince the council that runs Tortuga to ally with the pirates when it comes time to topple The Company.

Exports are exotic food and spices, and gold from a mine on one if the islands. But the placement of the Southern Isles makes them a hub for trade. It is by far the quickest route for many neighbouring nations, it takes a long time to sail around them. So many still take their chances with the pirates.

People come to the isles to disappear, or in the hopes of adventure and fortune on the high seas.

Ooh you’re challenging me here!

1. We’re talking ship’s biscuit/hard tack and salted meat for the most part. If they want to up morale they might buy spices or other dried ingredients. And yes, savvy quartermaster would also buy fresh fruit/veg regularly to supplement this. You’ve made me realise that the party hasn’t done this yet, so unless they stock up on fruit at the next port, they’ll start getting scurvy amongst the crew. Magical refrigeration would be possible, but expensive and rare.

2. Yes it would be tricky to find a competent ship’s doctor who was willing to join a pirate crew. Magical healing may be more realistic, most would not help with scurvy. Experienced sailors would know about the need for regular fruit/veg.

3. Contagious disease is definitely a thing that could happen, and the cause could be natural infections or germs, or just as easily a curse, demons, divine intervention. I don’t think there would he much knowledge of germ theory per se, but even during the plague people know to quarantine the sick. It would be hard aboard a ship and the crew may resist it though, yes.

4. Battle wounds could be treated either wit mh magic or the use of surgery or regular medicine. Infections are a problem and they are most likely to simply lop off the offending limb, resulting in wooden legs and hooks for hands, etc. Because I agree those are absolutely necessary.

5. Interesting question. I’d say it largely depends on tge Captain. Generally conditions aboard a pirate ship are much better than sailing in a navy, or for the Southern Islands Company (and i think this is largely historically accurate). They are better paid and more highly valued. And they have a say in how the ship is run. There had to be some incentive to join tgenoirates rather than the navy). That said, there are some more ruthless pirate captains who treat their crews worse and see them as more expendable. Its up to the party how they run their ship, but if they mistreat the crew too badly, they may have to deal with a mutiny.

I tried to do it, hopefully I did it right!

Yep, the pirate captain that helped them take their ship do so on the condition that they implement some version of The Pirate Code. All major decisions are decided by vote, with each crewman also getting a vote. In practice I would rarely have the crew vote against the party, just cos that’s no fun. But morale has been getting low, and if they don’t address it, they may decide they want a new Captain and try for a vote, giving the players a crisis to deal with.

Loot is also shared out equally, except the captain/officers get two shares. The players decided that they all collectively share the position of captain, while also having other roles. So they all get twice what the crew gets. I believe this is pretty accurate historically.

I just let the players decide the route though, I’ll only get the crew to protest if they haven’t taken a prize for a while, or if I think the crew would have an issue with the specific destination they choose. One of the players has the role of navigator so she does a check to see if she does a good job of that. If she doesn’t, I roll on my encounter table and something gets in their way, slows them down, or attacks.

We have a death cleric, a transmutation wizard, a bard and a fighter. So it won’t come up, but I’m allowing most things, I want the vibe of the campaign to be fun and chaotic and it’s worked well so far