Encounter of the Week: Sharkfin Shipwreck

 This week’s encounter is Sharkfin Shipwreck, an exploration and skill challenge encounter that pits the characters against the tempestuous power of nature itself. Pray to Umberlee for mercy, or pray to Kord for strength—you will need all the help you can get on the unrelenting waves. This encounter comes hot on the heels of the announcement of Ghosts of Saltmarsh, the next hardcover D&D adventure! This encounter is technically unrelated to the upcoming adventure, but Saltmarsh has more than a few storms, ships, and sahuagin within its pages, so this encounter could work as a teaser adventure now to whet your players’ appetites—or you could use it as a prologue to Saltmarsh when the adventure comes out.

Or, as always, you can use this encounter to add depth to a campaign of your own devising. The choice is yours.

Skill Challenge Encounter: Sharkfin Shipwreck

This skill challenge best-suited to characters of 1st level, but can be scaled up to challenge a higher-level party.

This was supposed to be an easy voyage across a few miles of open water.  The seas are supposed to be blessed with calm winds and placid waters at this time of year. But no true sailor ever leaves port without preparing for the worst. The characters are traveling from one port to another—it could be the town of Saltmarsh, or another port town from your own campaign. In order to make the journey, they booked passage on a trading vessel named the Sharkfin. This famous, double-masted caravel went on small journeys, carrying cargo from port to port along the coast, occasionally taking short journeys across open waters.

The Sharkfin’s captain is Grendanna Stormbreaker, a chaotic neutral, female half-orc pirate captain with a heavily scarred face and a wild mane of graying red hair tied down underneath a bandana. Few would call her beautiful, but Grendanna cares nothing for beauty. Nevertheless, her features are powerful, and she projects a powerful, authoritative charisma. She is the veteran of countless naval skirmishes, and she has the full trust of her crew. Grendanna’s first mate is a muscular, tattooed veteran of the waves; a neutral good, gnome thug named Rackham Byrne.  

But while the skies promised smooth sailing, some unknown power has caused this voyage to take a turn for the worse. Perhaps Umberlee frowns upon this voyage. Perhaps a darker, more primordial power has taken up recent residence. The Sharkfin is a bold craft, but she is merely a trading vessel. Skilled seafarers can save their wayward craft from certain doom if fortune smiles upon them, but most ships are fated to be dashed to flinders in a storm as vicious as this.

This encounter assumes that the characters have already booked passage on a ship. If your party hasn’t already chartered a vessel, boarded it, and made their way onto the high seas, you may have to create your own prelude to this adventure. Alternatively, you can begin this encounter in medias res as the characters are awakened by the cries of the first mate, and called to the deck of the ship.

Encounter Summary

While sailing across the open sea, the characters’ vessel is caught in the gnashing jaws of a terrible storm. They must attempt two skill challenges: one to prepare for the oncoming storm, and one to weather the storm itself. If they are unable to succeed on the second challenge, their ship is dashed against the reef, and they may all fall unconscious. When the entire party awakens, the storm has passed, but the reef is swarming with sahuagin scavengers. In their weakened state, they can fight or sneak past the sahuagin to one of the miraculously intact lifeboats and flee to shore.

Encounter Start

It is late at night, about eighteen hours into a twenty hour voyage. The characters are resting in their cabin on the Sharkfin. A storm is brewing, and the captain has just alerted her crew. When the first mate comes downstairs to awaken the characters, read or paraphrase the following:

When you went to sleep in your cabin below the decks of the Sharkfin, Captain Grendanna assured you that you would dock by daybreak. When you retired for the evening, the gentle rocking of the ship atop the placid sea lulled you to sleep. After what seems like only a moment’s slumber, you are jolted awake by a frantic knocking at the door.

If there are any elves in the party, note that they are actually awake. They have completed their four-hour-long trance and are now reading a novel, writing in a journal, or otherwise passing the time. Then, continue to read or paraphrase the following:

A muscular, tattooed gnome with thick red facial hair pushes open the door—you recognize him as Rackham Byrne, the Sharkfin’s first mate. He pounds on the door to make sure you are awake, and shouts, “Up, you lot! There’s a storm coming this way, and it’s a right howler. I know you ain’t part of the crew, but we’re preparing for the storm double-time. We need your help, or we’re going under, I guarantee it. Who’s coming?”

Any character who follows Byrne abovedeck is greeted by a dark sky and low, distant rumbling. Tiny flashes of lightning can be seen in the distance, illuminating the rocky shoreline nearby. A half-dozen sailors are running to and fro, preparing bailing buckets and tying safety lines around their waists. Since most or all of the characters are passengers, not sailors, Byrne makes some suggestions of tasks they can perform to help ready the Sharkfin for the storm. Consider printing this table out and giving it to your players as a handout, to help them decide what actions they want to take.



Ability (Proficiency) Used

“Batten down the hatches.”

Throw canvas over the cargo hatches on the deck to prevent the lower decks from flooding.

Strength (Athletics)

“Secure the gear.”

Tie down all loose gear or cargo to prevent it from flying around dangerously during the storm.

Strength (Athletics)

“Strike the Royals.”

Climb to the top of the mainmast and lower the highest sails to stabilize the ship.

Dexterity (Acrobatics)

“Plot a course towards safety.”

Use navigational tools to point the ship in a direction that will allow it to ride the storm, rather than be broken by it.

Wisdom (Perception)

“Loose a prayer to Umberlee!”

Try to assuage the coming storm by praying to Umberlee, goddess of the wrathful sea.

Intelligence (Religion); leading the entire crew in a group prayer could be an unconventional Charisma (Religion) check.

“Rally the crew’s spirits!”

Keep crew morale up by starting a work song and getting the whole crew singing.

Charisma (Performance)

“Use your magic!”

Cast a cantrip or a spell that could help protect the ship.

Your spellcasting ability + your proficiency bonus.

Skill Challenge: Batten Down the Hatches!

In this skill challenge, the characters try to prepare the vessel for the storm using the sample actions provided above, or by improvising their own. In this skill challenge, each character’s turn lasts an hour of in-game time, and each character can only take one turn. On their turn, the character can make one ability check using any ability score and skill proficiency they like, as long as they can explain how this check could reasonably improve the ship’s odds of survival.  

A character succeeds on their ability check by rolling a 10 or higher, and earn one success, and earn an additional success for every 5 points the check exceeds 10. (For example, a roll of 21 earns the character three successes.) Note how many successes the party scores in total. Failing a skill check has no immediate consequences, but the characters will want to accrue as many successes in this skill challenge as possible, since every success will make the next skill challenge—weathering the storm—easier to survive.

Any characters that were awake when the skill challenge began—such as characters who do not have to sleep such as elves or warforged—are able to immediately leap into action, and have advantage on their ability check in this challenge. Characters with the Sailor background (or Soldier background, if they were a naval soldier) also have advantage on this check.

Skill Challenge: The Storm

A terrible storm darkens the clouds and splits the skies above with lightning. Howling winds tear at the sails and biting rain tears at exposed flesh. The time to prepare is over. The storm has come.

When hour of preparation is complete, the broad-shouldered and scar-faced half-orc known as Captain Grendanna Stormbreaker strides towards them and greets the characters tersely. If they scored at least 5 successes in the previous skill challenge, she also gives them her appreciation. “I must thank you. I don’t know how many of you were sailors in this life or a past life, but your quick work may have saved our lives. And your own. Steel yourselves. This storm is about to hit.”

Almost before she can finish saying it, the storm does hit. The waves crash into the starboard bow with enough force to nearly knock everyone on board off their feet. Now, the characters must help keep the ship afloat and on course long enough to sail through the storm.

To successfully complete this skill challenge, the characters must make three successful ability checks before earning three failures. They can use any ability score paired with any skill or tool proficiency they wish, but a character cannot use the same ability score or proficiency two turns in a row. The DC of this ability check starts at 19, but is decreased by 1 for each success the party earned in the previous challenge. Additionally, at the start of every turn after the first, the DC increases by 1 as the storm increases in intensity.

If your players seem stuck, or can’t think of a good action to take during this skill challenge, you can suggest some course of action, and figure out what a good ability score and proficiency combination would be. A character who wants to make a Strength (Athletics) check could bail water. A character who wants to make a Wisdom (Survival) or Intelligence (Nature) check could advise the helmsman on how to navigate through the storm, and so on.

At Higher Levels: If the characters are at least 5th level, the starting DC of this skill challenge is 24. If the characters are at least 11th level, the starting DC is 29. If the characters are at least 17th level, the starting DC is 34. Additionally, if the characters are at least 11th level, creatures without resistance or immunity to either cold or thunder damage have disadvantage on their ability checks during this skill challenge. Finally, if the characters are at least 17th level, creatures without resistance or immunity to both cold and thunder damage have disadvantage on ability checks during this skill challenge.

Success: Just a Little Turbulence

If the characters earn three successes before three failures, the Sharkfin is slung through the storm by its powerful winds, and somehow manages to slide safely into port. The characters reach their destination only a little worse for wear. The characters each earn enough XP to advance to 2nd level.

Failure: Run Aground

If the characters earn three failures before three successes, the Sharkfin is tossed about in the ocean’s grip like a ragdoll, until it is flung into a reef about two miles from shore. The force of the ship’s bottom dragging against the reef does more than tear through the wood; it also jolts the vessel so violently that both masts crack at once and crash down upon the deck. Then, the retreating wave cracks the ship on its port side, causing the entire vessel to roll onto its side. The next wave picks the ship up and hurls it one hundred yards forward, spinning it upside down and smashing the entire vessel to flinders.

Any creature with fewer than 6 hit points is killed instantly, which includes the entire crew. Anyone else, including Captain Stormbreaker and her first mate, must make a DC 25 Constitution saving throw or fall unconscious. Unconscious creatures—such as the characters—awaken one hour later surrounded by sahuagin.

Sahuagin Scavengers

The shark-toothed raiders that prowl saltwater shores are known by many names, but most humans call them sea devils, or sahuagin. When the characters awaken, they are at half their maximum hit points and huddled against a mussel-encrusted boulder in the middle of a rocky reef. About 50 feet away are a number of sahuagin equal to half the number of characters, rounded up. They have not noticed the characters, but once they wake up, each character must make a DC 15 Dexterity (Stealth) check or alert these perceptive scavengers.

Each of these sahuagin have looted 2d10 sp from the wreck of the Sharkfin. If you want to include a magic item in this adventure, perhaps Captain Stormbreaker was smuggling a magical item—like a trident of fish command in the hold of her ship, and now one of the sahuagin is wielding it.

A 20-foot-wide hunk of the Sharkfin’s hull is stuck against the reef about 60 feet away. If the characters can reach it, they can paddle it back to shore in a few hours. They won’t emerge from this harrowing experience with any treasure, but they do earn enough XP to advance to 2nd level, plus any XP gained from fighting the sahuagin.

At Higher Levels: If the characters are at least 5th level, a sahuagin baron and a sahuagin priestess have joined the fight. Don’t adjust the fight further for higher-level characters; these sahuagin wouldn’t send a larger force to scavenge a wreck. Let the characters enjoy beating up a group of vultures after barely surviving a shipwreck.  

Did you like this adventure? You can pick up more adventures I've written on the DMs Guild, such as The Temple of Shattered Minds, a suspenseful eldritch mystery with a mind flayer villain (for 3rd level characters). My most recent adventure is in Dragon Heist: Forgotten Tales, a book by the Guild Adepts which gives you a new beginning, middle, and end to Waterdeep: Dragon Heist. It's the perfect way to give this adventure even more replay value! My new beginning is a great way to introduce a campaign focused on either the drow or devil cult factions causing trouble in Waterdeep. 

If you want Adventurers League-legal adventures, take a look at The Cannith Code, set in the magic-punk Eberron campaign setting, All Eyes on Chult, a high-stakes adventure set in Port Nyanzaru included in Xanathar's Lost Notes, or Fire, Ash, and Ruin, a demon-filled dungeon delve in an active Chultan volcano! This post contains DMs Guild affiliate links, which means that I—James Haeck—get an extra 5% of the sale if you buy anything from the DMs Guild using these links. You don't pay any extra, but your purchase helps support my work. Thank you so much!

Also, for more free encounters, take a look at the other encounters in the Encounter of the Week series!

James Haeck is the lead writer for D&D Beyond, the co-author of  Waterdeep: Dragon Heist and the Critical Role Tal'Dorei Campaign Setting, the DM of  Worlds Apartand a freelance writer for Wizards of the Coast, the D&D Adventurers League, and Kobold Press. He lives in Seattle, Washington with his partner Hannah and their feline adventurers Mei and Marzipan. You can usually find him wasting time on Twitter at @jamesjhaeck.


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