My (Untested) Theory of Nautical Campaigns

You know what I'm talking about. "The pirate campaign." "The wavecrawl." A "saltbox." "Maritime adventures." A notoriously elusive type of D&D campaign, for reasons fathomable only to those poor fools who've attempted it. And me, for I have infinite wisdom.

No really, I've casually mentioned this as being a "famously tricky" thing on several occasions and gotten a mix of confused stares from some and knowing agreement from others. But it's true. This shit is deceptively hard to pull off right. Today, I want to talk about the reasons why and the angles of attack to combat this. Because it's something nearly everyone who's ever been in this hobby has dreamed of at some point: buckling your own swash like a pro. Yarrr.

Reasons why it's tricky

There are some common pitfalls, although none of them are impossible to beat. DMs have been accomplishing this goal successfully for decades now, so don't take any of what I'm about to say as, "this is an unsolvable challenge." There are DMs who have solved these. But they're most often unanticipated challenges.

When people think of pirate adventures, the foremost activity in their mind will probably be sailing. So the act of sailing ships should have grand prominence in the campaign, yes? But how do you do that? Most editions of D&D have sparse, if any, rules to govern this. Or bad ones. So most DMs will have to homebrew a system for sailing gameplay. Which is great! But difficult to do well. Lots of them come up with some kind of minigame that feels more like you're playing a board game that night instead of D&D, and everyone came here tonight because they wanted to play D&D. "To take a naval action, you must spend a nautical token from the pool and add it to your seasick tracker. When your seasick tracker fills up, roll the barnacle die to determine a random crew member to lose their sealegs, removing them from participating in the rest of the trek. Once you've completed 5 treks, you finish the voyage." Fuck all that. So you have to make sure it's still anchored pretty heavily in the core gameplay components that make up D&D so it isn't alienating and irrelevant-feeling.

Artist credit: N.C. Wyeth. Not the best of the Wyeth
family, but definitely the most useful for
folks who are into RPGs.

One of the smartest approaches is to mimic the standard innovations of wilderness hexcrawl systems, another mode of gameplay that DMs have been iterating on for decades and making awesome with great game design efforts. It seems pretty close, right? Do a sandbox where the players have a map of an ocean and lots of islands to go to. Have an encounter prepared for every hex, or at least a random encounter table for the region. Piece of cake! Except... hexcrawls are also not a piece of cake and are often tricky to get right. 5E notoriously barely tried, and a lot of wilderness hexcrawl systems people make are... well they aren't bad, but they're usually either shallow or tedious. They're often intended as solid filler between dungeons, or when they are "the main activity of the adventure," it's usually still just for that one adventure. And I don't wanna hear any grognards chiming in their two cents claiming that hexcrawling is the easiest thing in the world and I don't know what I'm talking about. It's always the people most eager to say that who also run the most boring games.

And the comparison gets worse. There's all kinds of things you can add to hexcrawls to give them depth. Terrain types, different speeds of travel, foraging, tracking/hunting, lore checks, fog-of-war, weather, terrain hazards, resting hazards, resource scarcity, rolling to not get lost, etc. but not all of those translate to a "wavecrawl" context. And even the bread and butter of hexcrawls, random encounter tables... those are much trickier to fill out for the sea. There just aren't nearly as many monsters or creatures or sea-worthy NPC types you can reasonably expect to encounter on the surface of the ocean as you can on the land. One day you get attacked by ghost pirates, the next day by sahuagin, another you meet some mermaid sages, and on another you get attacked by a kraken, and so on... but the list probably isn't much longer than that if you just stock it with stuff from the Monster Manual. In fact, many of the ones that are intended for the ocean are nonetheless mechanically awkward to deal with. A sea serpent can rear up at you, but trying to fight off a bunch of water-bound mega-sharks from on deck is a bit weird. It'll probably inspire you to have lots of "non-creature encounters" like whirlpools and jagged rocks and stuff instead, which is probably better than "nothing but creature encounters everyday" anyway, but still: more work on your end, and only so many possibilities.

Now the more you think about this, at some point you'll probably think "let's focus on piracy itself, not just 'adventures on the ocean,' because that's really what the players want. They want to be pirates." Okay, now you have to come up with ship-to-ship combat rules, because that's what piracy itself actually is. Another new homebrew system to make that can easily be fucked up if you aren't a savvy game designer. Another system that often feels more like a board game than D&D.

Okay okay so you've been watching lots of pirate movies and have begun to think that you shouldn't emulate historical piracy so much as pirate fiction, since that's what your players are thinking of. And you think, "to be honest, most of the cool stuff happening isn't on the ships. It's the stuff that happens on the islands." So you focus on the sites of adventure. You'll handwave sailing entirely and do what you normally do as a DM with conventional campaigns, because as long as the dungeons are about digging up buried pirate treasure instead of taking a dragon's hoard, and the ancient tomb with all the puzzles is themed after Calypso instead of Vecna, and the big monster who you have to rescue an NPC from is a giant crab in a tropical jungle instead of an owlbear in a deciduous forest, then that's all it'll take for this to feel like pirate-brand adventuring™, right?

But it's about the structure of the campaign, especially over the long-term. If you just handwave the sailing parts, and all it takes for the players to get to any island you tell them about is to just say, "alright, so we go there. Now what?", then the world becomes functionally indistinguishable from a campaign that took place entirely on land and could have been done by traditional faux-medieval adventurers. The players won't feel the difference if you don't do anything to make it felt. After a certain point, the players will forget that they're actually pirates and that there's supposed to be a lot of sailing going on. No amount of "flavor text" description during your scene transitions where you talk about the sailing will ever be remembered as well as finding a way for them to play out the sailing. So we're back to square one.

The few people I know who have had a well-received pirate campaign still... cheated. At least, that's how I feel. They did the modern New School method of railroading their players from one pre-made encounter to the next. Sure, they had the variety of ship combat, island adventures, and sword fights with the law that you need in pirate fiction. But come on, it needs to be a sandbox. It's fucking sailing. It's the definition of freedom. If the PCs are just passengers or crewmembers on the ship rather than its leaders, then what's even the point?

Solutions

Something I see a lot is people just going for cliches or maybe a model to follow. "I love Pirates of the Caribbean, so I'll just put all that stuff in!" or "I've played Wind Waker, like, ten times! I'll just steal its map and islands and not tell my players!" This saves you some of the heavy lifting, don't get me wrong. Personally, the number one source I'd be plundering is some Sinbad the Sailor stuff, either the traditional tales or the Ray Harryhausen versions.

But I believe in finding structural solutions. Probably the most recent prominent attempt to solve our problems is Ghosts of Saltmarsh, the 5E pirate book by WotC. How is it? By most accounts, kinda bad. But after seeing Questing Beast's interview with Rebecca Chenier a few years ago, I found her thoughts promising enough to back her crowdfunded Weird on the Waves product, which I can confirm turned out to be pretty dang good. [EDIT: upated this paragraph based on new info] There is wisdom and resources found in those pages which can supplement the things I have to offer here, if you want more.

My personal theory? As cliche as it sounds, the key is balance.

Trying to lean too heavily on one thing to carry the campaign will inevitably stress it too much. There should be sailing rules for sailing gameplay, but so long as sailing gameplay takes up, like, 1/6th of the game rather than 4/6th or 5/6th then the rules don't have to be that deep. What are the other 5/6ths? Well one would be seaborne combat and another one would be the adventures on islands and dungeoncrawls and stuff (use short dungeons in this campaign, ya hear?). Normally, people would stop here and only have those three activities, but I actually think there are some other pirate-y activities that we could use to fill out the other 50% of the campaign.

1. Lots of DMs neglect to have social challenges between the crew. And I mean instead of just having a colorful list of fun NPC crewmates to meet, you should get downright political and have lots of drama and intrigue and backstabbing and history among the crew. Mysteries, disagreements, ethical dilemmas, etc. When you spend months at sea with nothing to do but talk, the gameplay should probably reflect political D&D more than anything else. Use some of your favorite PbtA story game-y stuff here or some of that Hillfolk drama system stuff I hear about. Have some old feuds, love affairs, maybe a mutiny or two.
2. Domain-level play. I know, I know, I'm always advocating for that stuff. But come on. Customizing your ship, and then later your fleet, as the party's shared HQ is a no brainer. I'm sure someone's made a pirate version of Blades in the Dark, but they must not have done a good enough job because this is such a good fucking idea that I should be hearing people singing about it at least as often as... well, as often as I hear people singing about Blades in the Dark. You can solidify the gameplay loop of "downtime in port, pick a score/quest/treasure thingy/whatever, sail out to that score and have some random encounters along the way (weather, terrain, monsters, pirates, merchants, blockades, etc.), then do the score on an island."
3. Miscellany. First of all, dice gambling games. The easiest thing is to just actually play Liar's Dice because it's really simple, you already have all the supplies, and players will like it. Second of all, maybe monster crafting stuff? As in, harvesting parts from the monsters you kill to do some cool crafting and alchemy stuff. The issue with this is that it's literally just whaling, and whaling is horrible. But it's also a pretty big component of the culture and lifestyle of that time and place in history, so maybe... fuckit, embrace the whaling. Pick out some appropriate sea shanties to sing while you do it so you can drown out the guilt.

And don't worry, I have some advice for the "big three" things as well.

Sailing: steal from Traveller or Stars Without Number or something. Either hexcrawl or pointcrawl. A pointcrawl would be nice since you'll always be going from island to island, so you technically CAN pre-calculate every distance the party will ever go. But the more islands you have, the more lines you'll have to draw! In any case, keep it pretty simple and focus any depth on the challenges that happen along the way. Players like playing as their individual characters, not as one large shared boat. It isn't easy to find a role for each crew member to contribute, so don't try.

And like I said about hexcrawling above, don't try too hard to emulate those norms. Hexcrawls on land are typically quite dense. A high variety of terrain types + several discoverable sites per hex are two common lynchpins of many hexcrawl systems. But the ocean is mostly ocean, and you needn't strain yourself to make it more than that. In fact, "equivalent density of content" would require that you take the same amount of content and spread it way further apart, because ships travel faster and for 24 hours/day compared to overland journeying. There should be lots of empty hexes!

You want the journey between islands to have a little bit of gameplay to chew on, but I don't think intense ship-navigation and logistical management is the way to do it. Instead, just hit them with a big group challenge, like, once or twice per trek. Make them discuss their choice among several options.  Every route has at least 2 major complications + you roll for a random encounter and then cross them against each other. So firstly, they can clearly see on the map: "do we run the blockade or go into the icy water?" or, "do we go past Scylla or Charybdis?" and then you also throw at them a random thing, such as pirates, bounty hunters, hazardous weather, an accidental fire breaking out on the ship, some sea monsters, etc. Dealing with a combination of 1 chosen problem and 1 or 2 unexpected problems simultaneously is a great way to generate excellent, memorable encounters that will sufficiently spice up each trip.

And more than just routes being drawn connecting island to island for travel, some routes should also be tagged for trade types. "Fishing route" "spice route" "slave route" "treasure route" and so on, so that players also always have the option of today's score just being "we want to intercept the big Imperial merchant boat and pirate the fuck out of it" rather than go to some island.

Also, check out some historical Asian ships. They're fucking rad

Naval combat: if you keep it medieval, it's not difficult at all. Medieval naval combat is all about boarding the other ship, so it really isn't that different from normal D&D combat. Optional pre-boarding tactics may include crossbows, Greek fire, and even ramming if the ship is equipped for it, but it all leads to boarding eventually. If you insist on gunpowder though, then the naval combat system does become about opposed cannon fire. In that case, follow something like Guns of Icarus and give each PC a role, and maybe reduce the pre-boarding cannon fire exchange to a short minigame warmup. But again, it doesn't need to be super deep. You don't need a naval combat system that's so robust and diverse in its potential that you can use it 100 times and not get bored of it. It only needs to be good enough to use a handful of times and not get boring. Believe it or not, you only ever need to have, like, 4 naval battles in the entire campaign for it to be remembered as a significant portion of the campaign. Just make each one substantially different in the setup and that's most of the work done.

Sites of adventure: firstly, Coins and Scrolls once did a good review of many island adventures here, here, and here. Beyond that, novelty is your friend. Here's a checklist of islands/adventure sites you need:

1. The Mysterious Island, with everything added from all its many adaptations
2. Cyclops island (and anything else you liked from The Odyssey)
3. Mermaid coral palace
4. Pirate stronghold
5. Empire stronghold (British, Spanish, Dutch, whatever)
6. Giant turtle island
7. Belly of a whale
8. Sahaugin shipwreck dungeon
9. Flying city/island/sailors
10. Viking islands
11. The Grand Armada
12. Venice and other Italian maritime republics
13. Neverland from Peter Pan, probably by just stealing from the adventure by Andrew Kolb
14. Alcatraz
15. Your favorite actual Caribbean island (mine's Cuba)
16. Amazon Island
17. Candied Island from Flapjack (use Prismatic Wasteland's Big Rock Candy Hexcrawl for it)
18. Skull Island from King Kong
19. Ireland
20. Atlantis
21. Davy Jones' Locker
22. Japan, Singapore, or both
23. Cthulhu island
24. Island of Lotus Eaters to tempt the PCs to stay forever
25. Some noble aristocrat's pleasure flotilla

Now of course, that's not a structural solution like I talked about. That's just me doing some brainstorming for you. But I want to illustrate a point here. In a good sandbox, there is, 1) too much content for the PCs to use all of it, and it is, 2) all killer, no filler. It's like a buffet. They'll probably only go to most sites of adventure once ever, so none of them have to be super deep. In fact, I'd actually say that some of the more popular island adventures out there like Hot Springs Island and the aforementioned Neverland are actually too big and intensive to justify including. You can run an entire campaign in Hot Springs Island, since it has about an equal amount of content as the entire hypothetical wavecrawl I just described above. But remember: for players to feel like true pirates, they have to have some sailing. It's kind of like how there's never a whole Star Wars movie that just takes place on one planet. Part of what makes it feel like Star Wars is that there's a decent amount of planet-hopping per movie.

So yeah, I say that in an OSR campaign that lasts 10 levels, you should offer a buffet of about 20 to 30 sites of adventure, and then you should distribute treasure such that the players could do 1 or 2 islands per level. That way they'll feel like they cleared out most of what's on the map but without losing the tantalizing mystery of how much more is left out there to discover.

Oh, did I mention that Gold-for-XP is literally the ideal advancement scheme for a pirate RPG? It's never been my personal preference, but if I ever do pirate D&D then I'm definitely using it. And like Rebecca Chenier says, you gotta get that gold back to port to cash it in if you want to level up, meaning the return journey from an island or pirate score gets increasingly dangerous the more treasure-laden you are (since now a bunch of pirates and privateers are gunna be hunting you). You know how I said you should have a random encounter on every trek mixed in with whatever challenge is on the way? Well, whatever table you're using should increase the chance of "pirate" the more treasure the party has. Imagine it's a d8 by default but can increase to a d10, d12, or d20 and every result of 8+ is some variation of "pirate/privateer/bounty hunter/Imperial fleet attack."

Something that can give it a little bit more structure than just "total freedom" though is a bit of light gating mechanics. What I mean by that is that there should be some content that the players have to "unlock" through their adventures. Their starting map of the sea should have a lot of adventure sites already on it, but there should be even more that can be added later through discovery. Treasure maps are the obvious one you should use a few times, but also reading/hearing secret lore, getting a crystal ball, attaining the means to breathe underwater, defeating or deflecting something guarding an area like an Imperial Armada or the Kraken or a big Poseidon-y giant in a strait, etc.

In summary, just do a little bit of everything. None of the individual pieces need to be revolutionary, since the whole of the campaign can be greater than the sum of its parts. You don't need amazing sailing or amazing ship combat or amazing islands. You need lots of good instances of each. In fact, keep each section short. Do a lot of prep work, but go for breadth over depth. You don't need one pillar that's 12 feet tall, you need 6 pillars that are each 2 feet tall. You only need to have one underwater dungeon, even one that only takes a single session, for the players to forever remember that, "our pirate campaign was so goddamn piratey that it had an underwater dungeon!"

Just make it a good underwater dungeon or else you're fucked.

One last thing

 

Oh, and why hasn't someone suggested a nautical West Marches game? It's a no-brainer. The HQ is Tortuga, the shared map is a big old pirate map of all the locations the previous generation of pirates buried their treasure, and you put together ad hoc crews of pirates to go recover all of it now that the Empire has declined and pirates can come out of hiding. It can also have job listings for pirates, so it isn't just about discovery. Taking bounties and rescuing friendly pirate NPCs from ghost curses and liberating some enslaved peoples from Imperial ships and stuff is just as good. But seriously, pirate West Marches. Let's fucking do it.

-Dwiz