Undead Pirate Captain

Medium undead, neutral evil

Armor Class 17 (armor scraps)
Hit Points 102 (12d8 + 48)
Speed 30 ft., swim 30 ft.

18 (+4) 18 (+4) 19 (+4) 18 (+4) 19 (+4) 17 (+3)

Skills Athletics +7, Deception +6, Intimidation +6, Perception +7, Persuasion +6, Stealth +7
Damage Vulnerabilities bludgeoning
Damage Immunities poison
Condition Immunities exhaustion, poisoned
Senses darkvision 60 ft., passive Perception 17
Languages the languages it knew in life
Challenge 5 (1,800 XP)


  • Lightfooted. The undead pirate can take the Dash or Disengage action as a bonus action on each of its turns.
  • Pull Themselves Together. If the undead pirate loses a limb or other body part, it can reattach it.
  • Sea Legs. The undead pirate has advantage on ability checks and saving throws to resist being knocked prone.
  • Sunlight Sensitivity. While in sunlight, the undead pirate has disadvantage on attack rolls, as well as on Wisdom (Perception) checks that rely on sight.
  • The Moon Doesn’t Lie. Only moonlight reveals the undead pirate’s true skeletal form.
  • Undead Fortitude. If damage reduces the undead pirate to 0 hit points, it must make a Constitution saving throw with a DC of 3 + the damage taken, unless the damage is radiant or from a critical hit. On a success, the undead pirate drops to 1 hit point instead.


  • Multiattack. The undead pirate makes two sword and two tentacle attacks.
  • Longsword. Melee Weapon Attack: +7 to hit, reach 5 ft., one target. Hit: 9 (1d10 + 4) slashing damage.
  • Tentacles. Melee Weapon Attack: +7 to hit, reach 10 ft., one target. Hit: 11 (2d6 + 4) bludgeoning damage.


  • Parry. The undead pirate adds 2 to its AC against one melee attack that would hit it. To do so, the undead pirate must see the attacker and be wielding a melee weapon or have a free tentacle.


Skeletal pirates kidnap the crew of a flagship. After the prisoners are taken to the deck of a pirate ship, a tall figure pushes past the strange crew. It is the notorious undead pirate captain.

Curious Captain. This clever, devious monster is a terrifying opponent. The hidden tentacles in his back only reveal themselves when he attacks.

Legendary Leader. His rowdy band of pirates are very loyal. The captain assembled the motley crew, and they will do anything for him. Every band of undead pirates has their own captain.

Undead Nature. An undead pirate doesn’t require air, food, drink, or sleep.

Section 15: Copyright Notice

Monsters of the Wilderness: A Collection of Monsters for 5th Edition Copyright 2022 Cawood Publishing Author Andrew Cawood

This is not the complete section 15 entry - see the full license for this page