D&D 5E Creating an Interesting Naval Journey Encounter

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My pirate PCs are 6th level, with a ship of their own and a sea to sail her on! The next session will involve a perilous naval journey, but the group check mechanism seems sort of flat for what I envision to be a major setpiece. Does anyone have ideas to spice up this encounter into something more noteworthy?

I am thinking of something like combat, where a failed skill check results in damage to the boat. In the alternative I would want a successful skill check to increase the time increment before the next check.
 

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The old Dungeon Magazine had a series on the Isle of Dread. One of the encounters while sailing was that the ship entered a saragossa sea where the ship was slowly being drawn to the middle of the kelp where several other ships were being slowly destroyed. The PCs needed to travel to the middle of the kelp and destroy the undead plant monster holding them. Along the path was old ships with skeletons and such. The PCs were just travelers on the ship, but needed to deal with the situation before they could resume their journey. You could spice up the encounter with having a pirate ship chasing them and both stuck. Now the PCs have two enemies or even need to join with some of the pirates to fight the undead thing.
 

My pirate PCs are 6th level, with a ship of their own and a sea to sail her on! The next session will involve a perilous naval journey, but the group check mechanism seems sort of flat for what I envision to be a major setpiece. Does anyone have ideas to spice up this encounter into something more noteworthy?

I am thinking of something like combat, where a failed skill check results in damage to the boat. In the alternative I would want a successful skill check to increase the time increment before the next check.
Are you thinking of ship-v-ship combat or ship-v-sea monster?

Ship-v-ship - there's not much official out there though someone said something about there being some naval combat rules in the Ghostwalk d'oh! Ghosts of Saltmarsh guide.

Ship-v-sea monster is much easier. Just have the monster attack as normal and every so often either use the skill-check idea (if the PCs have any control) or just give the ship a saving throw (if they don't) to see how much if any damage it takes.

@aco175 's idea of ship-v-environment is a fine third option as well, and in fact is really cool! :)
 
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  • A whale is territorial or in rut, tries to ram the ship to chase it off.
  • Tangling kelp in a shoal area slows down the ship and must be cut off or magically harmed / removed. (Mage Hand with a rake might help.)
  • The ship is carrying a magic item that draws -hostile sea race- like a magnet.
  • If you can read the waves, you know where the shallow waters are (and aren't).
  • Storm a' coming. Try to steer around or outrun. Got Gust of Wind?
  • Maneuver through The Maze of sandbars while being chased by pirates / privateers / Coast Guard.
 

I like using linked skill tests for this sort of thing. Each check is it's own thing, and success or failure of each roll impacts the next one. So the if the crew fail to reef the sails during the storm the captain then takes a negative to his roll to pilot the ship. If you have a skill ladder or clock where success fills and failure empties, with success meaning you ride out the storm, and failure meaning something awful happens, I think you'll get the tension and drama you're looking for. So the big storm gets a clock with 8 segments, and the linked skill rolls either fill or drain one segment. Success of X over the DC could fill multiple segments. You can intersperse each linked roll with changing circumstances and obstacles.

You can link up the skill rolls anyway you like to add complexity and flavor. I'd probably use levels of success to measure each roll. So the reefing sails roll is, say, DC 12. Results under 12 give a penalty, 12 means success, and for every, IDK, 5 you beat the DC by the next roll in the chain gets a +1. Exceeding the final roll by increments of five fills additional segments on the clock.
 

You may run into problems with the crew and captain in some scenarios. In an environment encounter, the captain will want to keep control and the crew may be stuck between the PCs/ players coming up with ideas and telling people what to do and the captain needing to be the absolute authority on the ship. Heck, he may even tell the guards to lock up the PCs for getting involved if they are passengers and not the crew or owners. Of course, this can lead to needing the heroes to save them with their power and spells or even lead to mutiny with some of the crew freeing the PCs behind the captain's back.
 

The players are all the officers, so there should not be a problem with control.

I will try something like Fenris is proposing, with a failed roll leading to some ship damage. I will also keep track of the total margin from successful skill tests, using that as a rough guide to how far the ship has gone. At two intervals I will let them know when they reach the eye of the storm or whatever, and when they try going out the other side - probably upping the DC at both points.
 

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