Every ship has an anchor… 5E Pirate Battle


This is the story of the most epic and fun battle encounter I have ever participated in, as a DM or player, and of course, it’s on a ship.

Our players are getting ready to travel to the desert continent to retrieve a shadow dragon’s egg. They get on the ship, meet the dwarven captain, and set sail. The journey takes 18 days across the sea, they sit around, fishing, talking, and training for the epic battle against the shadow dragon.

On day 15, the Ranger says “I wanna talk to some seagulls, ask them about our destination“, of course he has Speak with animals, and the seagull tells him, there is a ship coming towards you.

They immediately know what’s up, and I’ve talked many times about how much I want to do a ship encounter, the dwarven captain screams and shouts for everyone to get ready, and it begins, the pirate ship comes at them, turns sideways and fires the cannons.

I open the combat tracker (we were playing on Fantasy Grounds) and they see a friendly NPC with their characters. “Ship    HP:370”.

Que up the theme from pirates of the caribbean! Literally, I started playing the music on Discord.

The battle starts with the cannons firing, and hitting the ship, “The ship takes 23 damage!” I say. The pirate ship is now near them, pirates on the ready to board the players’ ship, and we roll initiative.

Now they know, “We can drown at any moment, the cannons are firing, and our ship is taking damage!”

The dragonborn Barbarian‘s turn come up, he shouts “I jump to the pirate ship“, he rolls, he scores, he jumps, he then immediately runs to the anchor to release it! all the pirates were near the cannons, firing and ready to board.

DM: “What?”.

Barbarian:  “I want to release the anchor’s lock, it should drop down and stop the pirate ship”.

DM: “Ok… but your friends…? and you will be stuck with the pirates…”

Barbarian: “it doesn’t matter, our ship has civilians, I am not gonna let them get killed by pirates”

At this point I am stunned, I did not consider this outcome, and I totally forgot that every ship has an anchor of some kind, and when he asked me about its location, I told him it’s in the back. “He is going to ruin the whole battle…” I thought, but I like to reward my players for good thinking so I made him roll.

He of course succeeds the check.

DM: “Ok… fine, you release the anchor, it will take approximately 12 seconds to reach the ground, so we will continue this round and the next, and then we will see what happens”

The fight continues, pirates try to go hold the anchor from falling but it’s pretty tough especially with the Barbarian there protecting it. The PCs all jump to the pirate ship, one almost drowning, but they make it.

The anchor drops, the ship makes a sudden stop! all PCs make dexterity checks, 3 fail, making them prone.

The fight continues, including 2 friendly sailors who jumped with the players.

Courtesy of Stryxin

They fight their way through the pirates, throwing some pirates off board, and eventually winning.

After they win, the pirates, now scared, jump off ship to run away, they expected the ship to contain only civilians, and then comes the pirate captain, shouting and screaming at his cowardly pirates.

They fight the captain, in one of his turns, he uses the spell fire storm, the ship is now on fire, they carry on and throw him off the ship in an amazing feat of acrobatics and strength, they are the only ones on the ship now, and it’s on fire.

Ranger: “I jump down into the sea!”

DM: “What??!”

Ranger: “I have water breathing, so I am going to look around for the largest fish or whale or whatever I can find”

He finds a whale just chilling.

Ranger: “Mr.Whale, Can you please help us, can you jump as high as you can above to splash water on our ship? its on fire!”
Rolls high .

Whale nods… Ranger grabs into the whale, while the whale swims above water and jumps into the sky, everyone on the ship is floored by the sight, the Ranger jumps from the whale’s back, into the ship, rolls high to do an “amazing cool landing” as he puts it.

and he says to the party after landing oh so cool : “Meet my new friend“.

Water splashes, puts out the fire, the party now owns a huge f**king pirate ship, they ask one of the friendly sailors who survived to be a temporary captain until they reach the desert continent.

This was one of the most fun combat encounters I ever made, which was almost ruined…

So, always remember, when you want to make a cool pirate battle between ships and sailors and cool stuff, don’t forget…. Every ship has an anchor.

PS: Our ranger has asked me to include his character’s name, he is Klawed, the great whale whisperer.

About the author

DM Eaves

Been a DM for some years, currently running one campaign, one sandbox.
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