D&D 5E Actively Evil PCs & a Pirate Sandbox?

Its a shame I can only give XP for this post once.
Thank you - glad I could help.

Hadn't gotten as far as islands, yet, but you raise several good points, especially about Malaysia and Indonesia; I was wondering how I would go about drawing a map for this sort of thing with enough islands to actually be useful, and taking that area of the world would be a good starting point.
if you have access to Photoshop, or a similar program, this tutorial will ease your mapping woes:

http://worldbuildingschool.com/how-to-generate-random-terrain-using-photoshop/
 

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I have an idea about an undead king of a sunken kingdom that they mistakenly awaken at some point raising his undead legions from the bottom of the ocean to lay waste to cities, but that might be too....goody-two-shoes, and also feels like it violates the spirit of a sandbox in being too long an adventure to easily put into the world.

This is perfectly fine, sandboxes need things to be happening in the world. Just don't assume anything about how the PCs will react. Maybe they'll loot towns when everyone flees the undead hordes; maybe they'll try to join up. If they try to join up and the undead king turns out to be a Bad Boss, will they just resume pillaging aimlessly, or oppose him for revenge? That sort of thing.
 

This is perfectly fine, sandboxes need things to be happening in the world. Just don't assume anything about how the PCs will react. Maybe they'll loot towns when everyone flees the undead hordes; maybe they'll try to join up. If they try to join up and the undead king turns out to be a Bad Boss, will they just resume pillaging aimlessly, or oppose him for revenge? That sort of thing.

Actually, I just got an idea, from an imgur post I saw. The island the undead king/lich raises is a necropolis, and the party knows that the island is filled with treasure, and their livelihood as pirates would be threatened by world destruction.
 

Here are a couple of blog posts about "wavecrawls":

https://muleabides.wordpress.com/2011/03/06/saltbox-test-run/

http://dndwithpornstars.blogspot.ca/2011/04/wavecrawl-kit.html?zx=f92993e785b495e0

If I were to tackle this, I'd try to design the map so that it was full of interesting choices. For example: there are two ways to get to Tortuga (where you need to go to sell your stolen booty); the first way takes a long time (a week, let's say) but it's safe; the other way takes only a day but it requires you to go through a dangerous strait filled with reefs, hidden shoals, dangerous gusts of wind, sea monsters, and/or a fort that guards its mouth. A map of an empty ocean needs more time and thought to become interesting than a land-based map - you can't just throw down a mountain range here and a forest there and a river with spanned by only one bridge. Think in terms of bottlenecks and decision points. It might be a good idea to look at a board game and translate that (any boardgame should work, it doesn't need to be ship-based).

I'd also try to make time a PC resource. PCs can spend time to do stuff, like upgrade their ship, train their crew, increase morale, take a job and make some cash, and anything else you can think of. The cost is that the empires grow more powerful over time, strangling piracy with convoys protecting their merchantmen. Some kind of random event generator - civil war in England! the king of France is dead! revolution! war! etc. - that you roll on every month or so might shake things up as well, so PCs can't sit on a load of booty and expect that they'll buy it in Kingston because you stole it from a Spanish ship; England and Spain have ended their war, and part of the concession is that they must turn over their privateers to the other side. Stuff like that will give the players more interesting decisions to make: should we fix our mizzen-mast now or try to limp into port?

No idea how you want to handle mechanics. Sticking to simple checks probably won't cut it. Hit locations and various effects (like "Main Mast: AC 20, HP 15, if damaged the ship cannot sail" or whatever) might work out well. Skill challenges would probably work out here, because "navigating through a storm" is a pretty abstract situation. Anyway, I'm sure there will be some good ideas here.
 

Here are a couple of blog posts about "wavecrawls":

https://muleabides.wordpress.com/2011/03/06/saltbox-test-run/

http://dndwithpornstars.blogspot.ca/2011/04/wavecrawl-kit.html?zx=f92993e785b495e0

If I were to tackle this, I'd try to design the map so that it was full of interesting choices. For example: there are two ways to get to Tortuga (where you need to go to sell your stolen booty); the first way takes a long time (a week, let's say) but it's safe; the other way takes only a day but it requires you to go through a dangerous strait filled with reefs, hidden shoals, dangerous gusts of wind, sea monsters, and/or a fort that guards its mouth. A map of an empty ocean needs more time and thought to become interesting than a land-based map - you can't just throw down a mountain range here and a forest there and a river with spanned by only one bridge. Think in terms of bottlenecks and decision points. It might be a good idea to look at a board game and translate that (any boardgame should work, it doesn't need to be ship-based).

I'd also try to make time a PC resource. PCs can spend time to do stuff, like upgrade their ship, train their crew, increase morale, take a job and make some cash, and anything else you can think of. The cost is that the empires grow more powerful over time, strangling piracy with convoys protecting their merchantmen. Some kind of random event generator - civil war in England! the king of France is dead! revolution! war! etc. - that you roll on every month or so might shake things up as well, so PCs can't sit on a load of booty and expect that they'll buy it in Kingston because you stole it from a Spanish ship; England and Spain have ended their war, and part of the concession is that they must turn over their privateers to the other side. Stuff like that will give the players more interesting decisions to make: should we fix our mizzen-mast now or try to limp into port?

No idea how you want to handle mechanics. Sticking to simple checks probably won't cut it. Hit locations and various effects (like "Main Mast: AC 20, HP 15, if damaged the ship cannot sail" or whatever) might work out well. Skill challenges would probably work out here, because "navigating through a storm" is a pretty abstract situation. Anyway, I'm sure there will be some good ideas here.

That's a great idea, too. Hm; I need to look at...Admiral of the High Seas, is that what it was called? The ship fighting probably needs special maneuvers that a person can take, as well as multiple target areas (hull the ship vs. bring down the mast), as suggested.

I think I will have a "home base" for the Pirates, maybe a floating city, something like Venice or Florence, which would amuse me greatly having been there, where the majority of the Pirates have their home base, and its a fairly lawless sort of town; to enforce the "Time as Resource", perhaps taking a page from Adventurer's League and having "Downtime" that can be spent on stuff after each quest or similar (probably need a ship upgrade chart, too, come to think of it), but how detailed should the "timeframes" be; should there be political things happening while the party is uninvolved that change the outcomes of things that they think will work (to use the "king of france is dead" angle, as an example)?
 

but how detailed should the "timeframes" be; should there be political things happening while the party is uninvolved that change the outcomes of things that they think will work (to use the "king of france is dead" angle, as an example)?

In a way the timeframe will be based on the PC's ability to refresh limited resources (HP, including ship HP and repairs, and magic). That's not too big of a deal; you don't want the PCs to out-level the world in a couple of weeks because they are able to get large amounts of XP every single day, but with travel times it's not likely to happen.

Otherwise, the limiting factor is how much bookkeeping you want to do as DM. If you've got the time and energy to keep track of every little plot going on in all the ports, go for it! But that's not necessary. Major plot threads - powerful NPCs, like a pirate captain, an admiral, a cult of Cthulhu - could be tracked, but what you really want to make sure you have a handle on is whatever the PCs end up doing and what they interact with. I'd go with a monthly roll for random stuff (stuff from the home countries, ports changing hands, a shortage of tobacco or other trade goods, new bounties, strange magical stuff, etc.) and keep a weekly handle on what the major players are up to.

One other aspect you might want to consider is rewarding XP for GP. I like to think of XP as the gas that fuels the game - you want to do x and y, you do it and get rewarded with XP, which end up changing your characters and allow you to do more x and achieve y (which was out of your grasp before). Awarding XP for GP will push the PCs to act like pirates. You might need to do some tinkering with the GP rewards to get the rewards correct but it shouldn't be too hard (divide the amount of a level 1 GP reward by the amount of XP needed to hit level 2 and that should be your baseline; level 3 to 4 might make a better baseline though).
 

In a way the timeframe will be based on the PC's ability to refresh limited resources (HP, including ship HP and repairs, and magic). That's not too big of a deal; you don't want the PCs to out-level the world in a couple of weeks because they are able to get large amounts of XP every single day, but with travel times it's not likely to happen.

Otherwise, the limiting factor is how much bookkeeping you want to do as DM. If you've got the time and energy to keep track of every little plot going on in all the ports, go for it! But that's not necessary. Major plot threads - powerful NPCs, like a pirate captain, an admiral, a cult of Cthulhu - could be tracked, but what you really want to make sure you have a handle on is whatever the PCs end up doing and what they interact with. I'd go with a monthly roll for random stuff (stuff from the home countries, ports changing hands, a shortage of tobacco or other trade goods, new bounties, strange magical stuff, etc.) and keep a weekly handle on what the major players are up to.

One other aspect you might want to consider is rewarding XP for GP. I like to think of XP as the gas that fuels the game - you want to do x and y, you do it and get rewarded with XP, which end up changing your characters and allow you to do more x and achieve y (which was out of your grasp before). Awarding XP for GP will push the PCs to act like pirates. You might need to do some tinkering with the GP rewards to get the rewards correct but it shouldn't be too hard (divide the amount of a level 1 GP reward by the amount of XP needed to hit level 2 and that should be your baseline; level 3 to 4 might make a better baseline though).

Hm. Gold for XP. I remember seeing a thread about that at some point. I wonder if it would be better to increase the leveling, or decrease the amount of XP earned via gold?

I get the feeling I'll be using and expanding the Monster Creation Tables in the DMG...I'm so glad I bought that book.


EDIT: After playing with the numbers a bit, I don't think that Xp-for-Gold will work as well as I'd like. So, I'll need lots of things for the group to spend their gold on; ship upgrades is an easy one, items, magic items (from the various schools, probably), slaves? Not sure if they're go for that or not. I think having and getting a house or stronghold somewhere is probably a good idea, too, as a way to spend money. Magic item creation is already expensive enough, so then its just a matter of expanding the other things.
 
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I think the biggest questions you'll need your players to answer are:

1) What kind of evil are they? Are they merely selfish and willing to let others come to harm for profit? Are they Evil and planning to take over/destroy the world? Both would have very different game implications.

2) What do they want out of the game? Do they have any specific intentions for their evilness (relates to #1)?

As for your questions about sandbox, 5e handles it as well as it handles regular adventures. It is, potentially, more difficult on you as the DM, because there isn't any real script - they instigate a change, you react as the world. To make a sandbox, simply create enough information about the world that you feel comfortable with ad-libbing the rest, then press "go." Notes about people and their motivations replace the normal adventure notes.

Hopefully that helps some.

I think you nailed some important questions with regard to how the characters are going to be evil.

I also wanted to point out that your sandbox comment is similar to something that I've read about writing fiction, "villains act, heroes react." This saying meas that heroes should have goals and should pursue those goals the way that real people would, but the heroes usually don't know about the villains or their poisonous fruit until the villains do something that draws the heroes' attention (either directly or by others sending for the heroes in response to the threat).



In an evil campaign, I believe the early levels involve the characters engaging in smaller scale evil: robberies, kidnappings, individual murders, extortion, and so on. As the levels increase, the characters become threats to the broader world: going from local villains, to nation-wide villains, to continental/global/planar villains. As the villains threaten more of the world, they will draw the attention of greater and greater heroes who will seek to stop them.

Also thrown into the mix should be villains whose plans will be disrupted by the villainous PCs: the lich who seeks a magic item the PCs have already looted, the bandit king who wants to terrify and extort a town that the PCs are robbing blind or have burned to the ground, and so on.
 

As I was writing last night, I wondered: how detailed do my nations have to be?

I also realized I a terrible at naming things.
 

what form of government do they have? What type of society do they have? Who appears to be in charge? Who is really in charge? Do the people at the bottom of the social order support the social order or are they forced to accept it? What about the people at the top? What are their military/magical forces like? How are they run? Who's in charge of them? Is it the same as the society as a whole, or different? Why? What members of society are most likely to balk at the status quo? What don't they like, why don't they like it, and how would they work to change it?

How would you describe the nation to a foreigner, and how would you describe the nation to a native (in a sentence or two)?

An easy way to do names: pick a language who's sound you like to represent the nation (let's use German); find an online dictionary/translator for English/German; look up words that describe what you want to name (like port, city, seaport, town, wet, wave, etc...); mash a couple of them together, change them a little if you want, and you have a name. Meerstadt sounds like a German city. Just be consistent.
 

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