D&D 5E Sea Voyage Advice?

not-so-newguy

I'm the Straw Man in your argument
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

I'm the Straw Man in your argument
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

I'm the Straw Man in your argument
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.
 

R_J_K75

Legend
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

I'm the Straw Man in your argument
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.
 

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