What good, popular setting you have used for "Pirates of the Caribbean" types of adventures? What makes it good for running a pirate game?
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The 7th Sea Role Playing Game is focused on swashbuckling adventures. The setting is designed to be similar to Europe in the 17th century, with the addition of a few magical elements.
The game comes in two flavors: A "roll and keep" system (similar to L5R) under the 7th Sea brand, and a D20 variant under the heading of Swashbuckling Adventures.
Personally, I've played the original "roll and keep" version a few times. The writing in the books focuses on over the top action, and weaving players' backgrounds and suggestions into the ongoing campaign. It's a lot of fun once everyone gets it, but can take a little getting used to.
The setting itself has a lot of political intrigue detailed, along with several ongoing storylines. Between the various nations, there is support for most of the tropes found in the swashbuckling genre.
Savage Worlds has a couple of pirate settings, including Pirates of the Spanish Main and the (out of print?) Fifty Fathoms magic+pirates setting.
Also, I just used it to run a Firefly campaign which involved some piracy...but in space, obviously.
And I can't believe I neglected Swashbucklers of the Seven Skies in my initial post! S7S uses an improved version of the Prose Descriptive Qualities (PDQ) system from Chad Underkoffler. It's decidedly not PotC - but it decidedly is swashbucklery goodness in a detailed setting bundled with a system that sits on my personal scale somewhere between "really good" and "excellent".
For a pirate game full of blood, smoke, and steel (as opposed to buckles and swashes), I would use The Riddle of Steel because of its fast-yet-detailed duel-based combat system and its mechanical support of revenge-soaked plots.
The combat system has that rare quality of being fast yet detailed, and is built to play duels in that fast and detailed way. It's a tactical die-pool system: you try to judge how much you can afford to put into offense and defense, with the manœuver you choose determining what you might accomplish (disarm, parry, strike, etc.) and any modifiers to your roll or dice pool. The manœuver you choose and the type of weapon you're using determines what target number you need on your dice, so that parries, feints, and thrusts are going to be easier with a rapier, but a sweep at the legs or a bash that powers through the opponent's defenses will be easier with a club.
Further, your dice pool is only replenished every second round. So not only do you have to split your dice pool across attack and defense, but you also have to decide how many dice to hold back for the second round. You can decide to play it safe and hold back a decent number of dice for the next round, at the risk of not committing enough dice to the current round to score a decisive wound on your opponent. At the other extreme you can try to "alpha-strike" your opponent in the hopes that their wounds will either debilitate them enough next round to be a minimal threat, or incapacitate them completely. Then the risk is that you'll have too few or no dice for the second round if you've judge (or rolled) poorly and they're still a threat, at which point you'll likely take an incapacitating or mortal wound.
Finally, unlike many duel-centric combat systems, it handles fights between multiple combatants without having to contort the system at all. It uses a natural feature of the combat system—splitting dice pools—to handle multiple threats and targets. Such fights are still as detailed as one-on-one duels, and are even more tactical since being outnumbered takes both character skill and player tactics to make the most of divided resources.
The speed of the system is accomplished by pre-calculating most of the numbers you need (target numbers, die pool totals), and because the core activities of a round—splitting your dice pools and comparing successes—is not time-consuming. A nice side effect is that, once you've done a few combats and it becomes intuitive enough, you can afford the time to more deeply strategise about your manœuvers and how to split your pools for more clever effect.
The mechanical support for revenge (and other goals and ideals) is in the "Spiritual Attribute" part of characters. It sounds foofy, but it's actually just a way to give your character a plot pacing mechanic (for things like "Take back the Amity" or "Kill that devil pirate Edward Teach") that functions somewhat like a character ability. They start as low as zero dice (no plot advancement), and when you're doing something toward your goal (like chasing down the sail of the Amity who was taken by Teach), all the relevant attributes increase by a die and you get to add the attribute's new dice total to all your plot-related rolls. Characters who are fulfilling their plots therefore get better at doing the plot-centric things they need to. They can also be "spent down" at any time to advance your character's other attributes (strength, etc.), so following your character plots also turns into character advancement.
The deadly combat system is tamed by Spiritual Attributes: they make the "probably die if you make a mistake" part of duels almost disappear for characters who are on-plot. A character has five Spiritual Attributes which range from zero to 5 dice (always changing during play as they're earned and spent on advancement), and if the game-play converges in such a way that they're all relevant, they are all added to the roll. So, you can go from having to split (e.g.) a 10-die pool among attack and defense during combat, across two actions, to having 30 or more dice to divide among attack and defense across two actions. Characters thus become avenging terrors exactly when the plot says they should: when all of their pains, desires, goals, and revenges come to a head in a single epic duel with their hated enemy.
Again, I would only use The Riddle of Steel for a Blood-Soaked Waves kind of pirate game. It could be used for a swashbuckling game, but it would be on the GM to make it light-hearted enough to fit the genre despite the gritty combat system. The Spiritual Attributes system could be bent toward that end just by making sure goals and drives chosen were up-beat. The GM would have to keep the game away from combats except at the climax, to keep players from encountering the "deadly" version of the combat system that happens when they don't have Spiritual Attributes to tame it.
I wouldn't necessarily use the setting that's included in The Riddle of Steel, and would develop or borrow a suitably-piratical setting from elsewhere instead. The system isn't tied to the default setting at all, fortunately. However, if you wanted to use the setting there are two regions that would be good for a piratical campaign: the Sea of Sail is a vague analogue to the South and East China Seas which would be good for Eastern-flavoured piracy; and the Sea of Fallen Gods, which borders the centre of the old Empire on one side and a number of free cities and nations on the other, with many isles scattered across the waters, which would give a more Mediterranean pirate game.
Finally, the game is out of print. Copies can be had from various second-hand dealers, but the publisher disappeared after the company changed hands a few times and then the latest owner (who is not same as the game author) had personal and financial difficulties.
GURPS Swashbucklers - covers the whole period rather than just the pirates. All normal GURPS strengths and weaknesses. Not specifically pirates.
7th sea - as noted by AceCalhoon. It is, however, an alternate earth setting, where christianity went the Gnostic route rather than the Pauline route most of us are familiar with. I believe it is out of print.
Arrowflight with it's supplement, Island Nations. The setting is a fantasy world in the early musketeer period, with fantasy races and swashbuckling. Excellent but simple martial arts, including a couple aimed at swashbuckling. Ship combat rules semi-abstracted, but easily adapted to minis. Drawbacks include system being dicepool based system in 1E and 2d6 roll low in 2nd, with no rescaling in CharGen (In other words, radically different odds.)
Savage Worlds has it's pirate settings. It also has a variation on Space 1889. This should allow several ways in to the issues of piracy. Said to be simple, point build.
My Points of Lights II has a system neutral (with some slight D&Disms) setting called the Misty Isles that I designed for pirate adventures.
It geography is mirrored off of the islands of Indonesia which were one of the historical areas for piracy. The political situation mirrors that of the opening of the Caribbean. In the Misty Isles there are two rival colonial powers (The Grand Kingdom and the Scarlet Empire) with colonies harvesting valuable crops (Indigo & Sugar). There was a recent war with an inconclusive end setting up a rivalry (like England and Spain). There are lost civilizations that can be found as well as unusual islands. (Like one where the flowers are so large that jaguars sleep in them).
Finally it is in a form that makes it easy for a referee to pick it up and start running it. It uses the hex crawl sandbox format of the Wilderlands and Traveller. I can see it easily be used with something like GURPS Swashbuckler with it's emphasis on character detail and technology notes. Or even 7th Sea.
The main difference is that I focus on local detail while most other pirate products focus on the high level detail.
And here's the 'out there' answer
Why not try Fiasco? Fiasco is a GM-less system for games about folks who are in over their heads. People who get involved in bungled capers that end up badly for everyone, rather like Cohen Brothers films like Fiasco, Burn After Reading etc...
To me, this seems like a great fit for capturing the feel of the Pirates of the Caribbean movies, where the protagonists are always going from the cooking pot into the fire (sometimes literally), have their own goals and motives, and don't always play nice together in a traditional RPG party.
Yarr! it's got to be worth a shot, you savvy?
I've had a lot of fun with Green Ronin's Skull and Bones game. It' uses familiar d20 rules, with a couple of added classes, equipment, and other fun toys.
Also, as the original poster referenced the Pirates of the Caribbean, Skull and Bones is set up as horror piracy already, with the addition of bokor, houngans, and other New World magic.
Green Ronin publishing has a campaign setting known as Freeport: The City of Adventure. It's a pirate city that has all sorts of Lovecraftian stuff going on in it. Most of their books are for D&D3E, but they are coming out with books for Pathfinder, and they have guides to help you use it with D&D4E as well.
Mike Mearls' Iron Heroes is surprisingly useful for a pirate setting. It's based on the familiar D20 system, with the following changes:
There are no rules for guns, but you can re-purpose crossbows or borrow gun rules from any other d20 system.