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D&D 5E Sea Voyage Advice?

not-so-newguy

Adventurer
In about a month, the group will disembark from Mirros and make the long voyage to the Isle of Dread. I rarely run encounters involving the sea and have never ran a whole campaign with a naval element to it. So I'm looking for some guidance/advice on this. Recommendations for PDF guides would be very helpful.

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A little bit of context: The group discovered Rory Barbarossa's ship log/map and are now picking up lucrative adventuring jobs to buy a pinnace*. The players are capable of handling the ship and do some rowing, but they'll need to hire 5 rowers; so they'll need supplies for 11 people total. There's a ranger and a druid in the group, food will not be an issue and water will only be a minor one ( enough Goodberry for everyone & enough Create Water for 10 of 11 people).

*I used this list of ships/boats:
 

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Quickleaf

Legend
I wrote something called The Buccaneer’s Bestiary - Dungeon Masters Guild - which has ~25 pages of random encounter tables for a Pirates of the Caribbean milieu. The tables often include nested tables and serve as adventure seeds, divided according to At Sea, Port of Call, Islands, Underwater, and The Abyss. There’s lots of inspiration there. Nothing systemic like a cohesive Of Ships & Sea section, but lots of imminently gameable ideas.
 

not-so-newguy

Adventurer
Sounds like a "You set sail and X weeks later your outlook spots land" kind of situation.
I haven't ruled out playing it that way, but I'd like to explore the possibility of adding a few encounters to the voyage.

Also, there are things to do around the island that require a ship. The players could decide to explore the outskirts of the island, meddle with the pirates who live on a small island, or go diving for pearls.
 
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not-so-newguy

Adventurer
I wrote something called The Buccaneer’s Bestiary - Dungeon Masters Guild - which has ~25 pages of random encounter tables for a Pirates of the Caribbean milieu. The tables often include nested tables and serve as adventure seeds, divided according to At Sea, Port of Call, Islands, Underwater, and The Abyss. There’s lots of inspiration there. Nothing systemic like a cohesive Of Ships & Sea section, but lots of imminently gameable ideas.
Within my price, I'll check it out. Thanks!
 

Blue

Ravenous Bugblatter Beast of Traal
They may want to carry supplies as well - both as a break from just eating a single berry a day (unless you want to raise what you are paying) and just in cast a caster is lost. :)
 


Yenrak

Explorer
It sort of depends on whether you plan to have things like ship to ship combat, pirate attacks, fun adventures at sea.

I recently DM'd my PCs on a sea quest from Waterdeep to Chult. There were quite a few encounters on the way. The most memorable and fun encounter was with a group of goblins lost at sea who did not understand the movement of the sun. They kept following the sun each day and would bring down the sails when the sun set. Then, each morning, they'd sail in the direction of the sun all day. Somehow they never got anywhere. My characters got them to shore! It was lots of fun.
 

The players could decide to explore the outskirts of the island, meddle with the pirates who live on a small island, or go diving for pearls.
There was an old 3E Dungeon Magazine adventure which IDR the name of. The players could get ahold of submarine made from a Dragon Turtle shell. I've let my players acquire this in more than one campaign and its always been lots of fun. Obviously you can make it up but I think it held only 4 medium creatures, wasnt very fast and only held so much air so they had to surface often. It was really handy for hugging the coast and sneaky up on unsuspecting victims.
 

not-so-newguy

Adventurer
There was an old 3E Dungeon Magazine adventure which IDR the name of. The players could get ahold of submarine made from a Dragon Turtle shell. I've let my players acquire this in more than one campaign and its always been lots of fun. Obviously you can make it up but I think it held only 4 medium creatures, wasnt very fast and only held so much air so they had to surface often. It was really handy for hugging the coast and sneaky up on unsuspecting victims.
Now why/how would a modified apparatus of kwalish end up in the Isle of Dread?🤔 food for thought.
 

I don't know how chaotic your players (and their PCs) are...
Ask yourself how important it is that the PCs arrive at the Isle of Dread. If they get encounters along the way, will the captain and navigator be at risk? What happens if they die or fall overboard? Can the PCs navigate and sail the ship, or will they run aground at some random location (to be decided by the dice)?
 

not-so-newguy

Adventurer
I don't know how chaotic your players (and their PCs) are...
Ask yourself how important it is that the PCs arrive at the Isle of Dread. If they get encounters along the way, will the captain and navigator be at risk? What happens if they die or fall overboard? Can the PCs navigate and sail the ship, or will they run aground at some random location (to be decided by the dice)?
The intention behind the voyage encounters would to reinforce the idea that the party is moving away from the familiar "civilized" world and moving towards a different, alien setting. Those particular encounters would be by design, rather than random dice rolls. That being said, all sorts of unfortunate (and fortunate) things may happen during the course of an encounter.
 

The intention behind the voyage encounters would to reinforce the idea that the party is moving away from the familiar "civilized" world and moving towards a different, alien setting. Those particular encounters would be by design, rather than random dice rolls. That being said, all sorts of unfortunate (and fortunate) things may happen during the course of an encounter.
Having encounters along the way to flavor the world and change the setting is great.

But be ready for the possible consequences of the combat/encounters. If you need to railroad that ship without a mast and no captain to the Isle of Dread, then it will still feel awkward to the players, albeit for different reasons.
 

aco175

Legend
The Dungeon magazine campaign for the Isle of Dread in 3e had several encounters while getting to the island. My favorite was the sargasso sea one with the ship becoming stuck in a vast bed of seaweed. The seaweed was controlled by some strange undead plant thing and the area also contained several other ruined ships with undead and supplies they needed to continue or maybe fix their ship. There could be NPCs there needing rescue or become workers on the ship.

The end of the voyage to the island had a bit of railroading when the ship was wrecked on the other side of the island and the PCs needed to cross over several elements to the settlement.
 

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