169 Dead Pirates


About this Resource

This resource features the general description of a hidden cove in a lonely island where a big treasure awaits hidden. It includes adventure ideas that are appropriate for low-level (Levels 1 to 5) adventuring parties. Challenge Rating (CR) is calculated using a party of four as the model.

The DM is free to change or modify any or all the information found here. NPC names and settlement names are the first the DM should consider changing to accommodate any homebrew world lore.

When monsters are referenced, book name and page numbers are noted in parenthesis. Be aware that page numbers may vary depending on the book print. If the DM can’t find a monster where noted, it means it is a different book print. Page differences tend to be small so whatever is missing will be reasonably close to the pages noted in the adventure.

Background Lore

There was a pirate lord a few centuries ago known as Harry Twisted-Tooth. He was the most powerful man in the oceans for a brief period of four years. It all ended for Harry Twisted-Tooth when his fleet was ambushed and surrounded by a coalition of two royal fleets from nearby countries. The came at dawn during the new moon. When the scouts saw them, they were upon them. Very few survived the attack, and those who did were simple-minded henchmen, the lowest of the low. No officers or captains survived, they all fought until the end. Even Harry Twisted-Tooth.

The royal fleet sacked Harry’s boats but they could never find his treasure. Not that they expected it to be there in the first place, but it was worth it to try. Harry Twisted-Tooth boarded and sacked thousands of ships, his men raided countless fishing towns; the size of Harry’s treasure was incalculable, and it was hidden somewhere. It is the most famous pirate treasure to this day, mainly because no one ever found it.

Except some did find it but never lived to tell the tale. There are only a few records from that time, mainly in old libraries. Some of them store old log sheets and dock journals that register the comings and goings of merchant ships to and from important settlements. It is recorded in these journals which ships were robbed and when. There are also a few records from the city watch after the interrogation of captured pirates. It was revealed that Harry Twisted-Tooth had built a kind of pirate citadel in a lost island in the middle of the sea. A safe haven for pirates of his fleet. The city watch disregarded this confession after Harry was killed, but treasure hunters that dug this fact decades later ventured to find that island.

They found the island but did not survive the sole guardian it had. Harry Twisted-Tooth befriended a dragon turtle that lived in a cave under the island. More than a friendship it was a business relationship. With the help of a wizard that helped with translating, Harry struck a deal with the dragon turtle. Every ship that wished to approach the island had to drop a heavy bag of gold or treasure into the icy waters to pay the toll. Otherwise, the dragon turtle would emerge and tear the ship to splinters. That first group of ambitious explorers did not expect the hull of their boat to collapse from the bottom in a split second. A few others have tried to approach the island unsuccessfully. The dragon turtle even had the audacity to move the destroyed ships to the only cove that has easy access to the island, since most of it is surrounded by rocky cliffs. There are currently five ruined ships in the cove, three of them are visible and only half submerged, the two others are at the bottom of the water in the cove and not visible from the surface.

Adventure Design

The dragon turtle (MM p. 119) is a mighty monster that the adventurers are not supposed to face directly. It is the king of the sea, the adventurers have no opportunity against it. Fortunately, the dragon turtle does not have time to pursue small game. If a ship approaches the island, the dragon turtle deals enough damage to capsize it and leaves. The icy waters and the island’s native creatures are threat enough to deal with any unwanted visitors.

This is a creative way to use an epic creature in low-level adventures. The DM is free to determine if the adventurers have a chance to avoid having their ship destroyed. If an adventurer wishes to take control of the rudder to try to avoid the dragon turtle’s attacks and the ship is capable of doing so, then the adventurer must make a Dexterity ability check. The DC is determined by the DM depending on the Average Party Level (APL). If the adventurer has a seafaring related background, he makes the roll with advantage. If the adventurers avoid the dragon turtle’s attacks and manage to reach the island, the dragon turtle gets bored and lets them be.

It is not within the scope of this resource to determine what threats or treasures are hidden on the island. The DM has full latitude in the adventures to come.

Adventure Hooks

If the adventurers stay in a coastal city or fishing town and go hunting for rumors in the local taverns or inns, they may hear the following information:

  • A local adventurer named Braya Daun has been looking for pirate treasures for years. He returned from the library a few days ago smiling and left the day after on his ship. He has not returned, I wonder what he found out.
  • A group of treasure scavengers left on their ship, the Holy Grace, two weeks ago. They should be back by now, they said they were trying to find a small island four days north-west. I own that ship! Would you be willing to earn a quick coin and go order those deadbeats to return my ship immediately?
  • I spend my days in the library, you know. A lot of valuable information is buried in those pages. Well, I found some of that, I know where a famous treasure is hidden and I want to go get it. But I need some muscle to come with me. What say you? We can split it into even parts when we get our hands on it.
  • Want to hear something crazy. A military boat stopped here for supplies and then left northwest. Some of the sailors bragged about their wealthy futures after finding a famous treasure from an old legend. Well, apparently all of them are dead except a single soldier. Her name is Darena and she came back swimming on a log. She is still in bed. The fisherman that found her said she was famished, sunburnt, and delirious. They said she babbled about a giant sea monster.






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