I'm a semi-fledgeling DM currently doing a campaign in a tropical setting where the party is probably soon going to be murdering the main command group of a pirate outpost (with ships/several hundred pirates). Now depending on how much they are going to kill I'm going to try and have them take over the outpost.

The thing is that I have no clue how I could fit piracy management into the campaign. Is there any material giving pointers as to how to have my party go into the pirating life? I'm looking for profits, costs (salary pirates, profit cut?, ship repairs/new ship costs?), chances for loot (d20s) and some way they can influence this.

I'd like to use this as a staging ground to get the exploration of the neighbouring islands running, so they will probably find maps or information during the raids.

The party is currently 6 players, lvl 2-3 and I intend them to rather easily level up to around lvl 12-15 during this set of games.

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    \$\begingroup\$ Have you looked at the rules for running a business in the Downtime section of the DMG/XGtE? If so, is there something lacking with those that you would like an answer to address? \$\endgroup\$ Apr 3, 2018 at 12:52
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    \$\begingroup\$ Thank you for your response. I hadn't heard of XGtE yet, so I've looked through the downtime activities crime section but it seems to be about single characters being in downtime. The above setup requires upkeep for (battle)ships, pirates (I would assume these to be different from 'normal' business employees) and the loot to properly support this. I'd also like to have the party be capable to join a raiding ship to increase the odds (thinking about using a loot generator in these cases). The upkeep costs in the DMG mostly covers buildings of a certain size, not an entire pirate village. \$\endgroup\$
    – user12042
    Apr 3, 2018 at 13:22
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    \$\begingroup\$ Doesn't a village comprise of several buildings of certain sizes? \$\endgroup\$
    – Slagmoth
    Apr 3, 2018 at 13:27
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    \$\begingroup\$ related: running a large business in LMoP \$\endgroup\$
    – nitsua60
    Apr 3, 2018 at 14:54
  • \$\begingroup\$ @GarretGang Don't answer in comments. \$\endgroup\$ Apr 13, 2018 at 19:44

5 Answers 5


My first recommendation: Don't do that...

At least not the way you're describing. Entrepreneurship has never been one of D&D's strong-suits.

If it were me, I'd have a little bit of roleplay and hand-waving for the party to set up the new pirate king and make nice with the rest of the organization. Maybe a small check cut to the PC's every season/year whatever (a stake in the "company", so to speak). Then, the party can cruise around the islands, impervious to the pirates because they're friends(ish), now.

As an added bonus, you don't have to play the "my little band of pirates" mini-game.

If you're bent on running an organization:

The Setup: 400+ (several hundred) people is a lot. They're going to need a lifestyle between 'poor' and 'modest' or better (2sp-1gp per day). Some of that can be made up with a few survivalists or farmers, but still. Not all of the people on the island(s) are going to be active-duty pirates, either. You're going to have invalids and children (and just people that aren't pirates).

The Requirements: With the above in mind, that means you're going to need a large amount of money coming in (read: being pirated) to keep 400 people happy(ish); somewhere in the realm of 75-400gp per day.

The Payout: This requires that the downtime rules be allowed to apply to npcs. For reference, a comfortable lifestyle "costs" 2gp per day.

You can work between adventures, allowing you to maintain a modest lifestyle without having to pay 1 gp per day.

the same section talks about being a professional:

If you are a member of an organization that can provide gainful employment, such as a temple or a thieves’ guild, you earn enough to support a comfortable lifestyle instead.

I think a "Pirate den" counts as a thieve's guild for this purpose.

self-sufficient living:

Proficiency in the Survival skill lets you live at the equivalent of a comfortable lifestyle.

So, IF you have enough "gatherers" (2gp-ish for farmers, fisherman, whatever) AND enough pirates (2gp ish for organized employment) AND enough schmucks (1gp-ish for other menial labor) to add up to around 400gp per day (or however many people you have) AND enough work/money leftover to upkeep this entire organization (ships/buildings/etc)...

Then, you should be able to provide and organize enough of a system to keep the various inhabitants of these islands functioning at a modest level or better, where your players can then skim the remainder as profit. Morale, however is a different issue (that I don't have any input on).

It's worth noting that going through a lot of trouble to "run" an organization, basically results in "players occasionally get a paycheck", which is the same as my first solution, but without all the thinking.

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    \$\begingroup\$ I like how contrived and painful your detailed example is... Really showcases why doing that is a BAD idea and how it quickly turns into a board game (not D&D). Well done, sir \$\endgroup\$ Apr 3, 2018 at 15:47
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    \$\begingroup\$ If you combine the simplicity of your first method with the story elements of your second method (run the organization but handwave most of it and boil it down to a bit of money every so often) you get... Rubiksmoose's straight-out-of-the-book answer. \$\endgroup\$
    – Zeus
    Apr 3, 2018 at 19:02
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    \$\begingroup\$ Thanks for you detailed response, I've chosen it as the best answer because of your added example. \$\endgroup\$
    – user12042
    Apr 5, 2018 at 8:08

Downtime rules for running a business are the best official option right now

Effectively, what you are trying to do is run a pirating business. Luckily, in chapter 7 of the DMG there are rules for using downtime to run a business.

Running a Business Adventurers can end up owning businesses that have nothing to do with delving into dungeons or saving the world. A character might inherit a smithy, or the party might be given a parcel of farmland or a tavern as a reward. If they hold on to the business, they might feel obliged to spend time between adventures maintaining the venture and making sure it runs smoothly.

A character rolls percentile dice and adds the number of days spent on this downtime activity (maximum 30), then compares the total to the Running a Business table to determine what happens.

There follows a table which contains various results that might occur from running a business. This is a highly simplified system and it combines profits, costs and other such concerns into one simple roll and one resulting number of money earned (or lost).

These are simple rules, but you can use them as a base to homebrew if they are not what you want

This may not be as in depth as you want, but it might be more fun depending on the group. Not every group likes dealing with number-crunching to the extent that calculating actual costs and profits might entail.

For better or for worse, 5e doesn't contain any rules for such a detailed system anyways as part of its design ethos of simplification.

So, if you really want to go the more detailed route, you are going to have to create/modify your own rules to support that. That being said, the rules above should at least give you a place to start even if they don't fit perfectly.

  • \$\begingroup\$ This is the correct answer, then for the exploration of surrounding islands, etc. I'd add in just some pirating adventures for the PCs run in the normal adventure fashion. \$\endgroup\$
    – Zeus
    Apr 3, 2018 at 18:59

I agree with the other answers, in that you should not overcomplicate things. However an important thing to note is that pirates weren't really salaried. If you look at historic pirate codes, then you find a lot of talk about shares and "no prey, no pay". In other words, what each individual pirate got, from the lowliest sailor up to the captain, was a certain share of the plunder that is left after the expenses.

If you keep this, you should be able to keep things quite light without resorting to handwaving. Think of it kind of like a franchise operation: Each pirate ship is independent and ideally self sufficient. After all, they will be on their own at sea, possibly for months. Whenever they come back into port, they take care of their upkeep on their own and then distribute their loot. This will involve a certain amount of shares for the outpost. How many shares there are is initially kind of flexible, which allows you to look at the inverse problem: How much money do you want the players to have?

Determine this, then set up some random table with the right average. (Or just fake it). Add some narrative for the players if they ask "This week marked the return of captain Sparrow. After six months at sea, he brought in a fine haul of thousands of pieces of gold. Your share amounts to 530gp an enchanted sword and this fine norwegian blue parrot." or "Yesterday, captain Rum finally arrived back in port. Sadly he brings no loot since he just sailed around the isle of wight until he got dizzy."

To this you could add the costs of the actual outpost, which I would treat similar to something like a keep in the DMG. This already includes the salary of a local garrison and everything. Your outpost will of course have some skilled workers to repair the ships, merchants to fence the loot and sell provisions, as well as an inn for the pirates to drink away their share. But they can also easily work as their own agents. You might just charge them rent to offset the cost of the garrison, without worrying about their day-to-day dealings.

This should keep things from getting tedious, while giving you a lot of options to send your players on a related adventure, like hunting down a rogue captain or having to hijack a certain ship to add to your fleet. If your players want to get more involved they could also outfit their own ship and take it for a cruise, netting them the additional captains share.

  • \$\begingroup\$ Thank you for your reply, I'll incorporate your concept of self-sufficient pirates into the story! \$\endgroup\$
    – user12042
    Apr 5, 2018 at 8:10

Pirates were notoriously not organized in hierachies. Most real-world pirate outposts had no control over the vessels or crews docking there.

If they take control of the outpost, the pirate crews docked won't care much, as long as the docking fees stay the same. So they are basically running an Inn, just on a larger scale. Which means you don't have to worry about loot and crew management.

From a meta perspective, you should discuss with your players if they want to turn an RPG into a management game or not. If they don't, you can simply keep the outpost as a background element, and when they are in need of money they can access it for that purpose. Make up a simple table that they can roll on determining how much profits were made recently and how much they can take, and define how often they get to roll on that table.

  • \$\begingroup\$ oh, interesting reading. I interpreted the situation more like The Pirate King episode of Archer; less like Tortuga in Pirates of the Caribbean. \$\endgroup\$
    – goodguy5
    Apr 4, 2018 at 18:56
  • \$\begingroup\$ Thank you for your response, Tom. I'll look into this option! \$\endgroup\$
    – user12042
    Apr 5, 2018 at 8:14

There is a Pathfinder source book called "Ultimate Campaign" which includes some rules for settlement management. Whilst the focus is more on building a fledgling kingdom then a pirate settlement, I found it very useful for my D&D campaign where the characters find themselves managing a settlement in the wilderness.

One of my key finding is that unless you are all keen business studies students, then petty book-keeping / business admin can get to be pretty boring topic for many players.

This can be addressed by letting them have a 'manager' or 'hireling' or experienced pirate perhaps, who does all of the admin and book keeping off screen. The players can then take on the bigger issues such "Which kingdom do we pirate against ?", "How to deal with the king's pirate hunters ?" or perhaps "How do we get these pirates to stop robbing and start trading ?"

  • \$\begingroup\$ Welcome to RPG StackExchange! Please take the tour! If you have any questions I'll be happy to answer them! \$\endgroup\$ Apr 4, 2018 at 17:51
  • \$\begingroup\$ Thank you for your input! I'll look into this book for ideas! \$\endgroup\$
    – user12042
    Apr 5, 2018 at 8:12

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