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Freebooters and Fortune Hunters

Habitat: Any; Treasure: Individual, Implements

Along with being competent warriors, pirates are accomplished seafarers who know how to sail and maintain a ship. While some loyally follow their captains’ orders, others place greed, superstition, or self-preservation over duty.


Pirates

The term “pirate” encompasses a broad range of seafarers, including vicious sea rovers, dogged privateers, cursed treasure hunters, and others who seek riches and fame on the seas.

Pirates might be allies, foes, wild cards, or some combination thereof. While they are the bane of merchants and coastal communities, they know secrets of the sea and how to avoid aquatic threats. More unusual pirates set their sights beyond the waves, using airships, spelljamming vessels, plane-shifting craft, or stranger vehicles to explore and raid incredible realms.


Pirate Flags

To terrify opponents and spread their reputations, pirate crews fly distinctive flags. Roll twice on or choose results from the Pirate Flags table to inspire what flag a pirate crew sails under.

Pirate Flags
1d8 
The Flag Show A ... 
With ...
1
Buccaneer
A captain’s hat
2
Dragon
Crossbones
3
Fiend
Crossed blades
4
Goat
An eye patch
5
Kraken
Lightning bolts
6
Merfolk
A mug of ale
7
Skull
A tattoo
8
Whale
A treasure chest

Actions

Multiattack. The pirate makes two Dagger attacks. It can replace one attack with a use of Enthralling Panache.

Dagger. Melee or Ranged Attack Roll: +5, reach 5 ft. or range 20/60 ft. Hit: 5 (1d4 + 3) Piercing damage.

Enthralling Panache. Wisdom Saving Throw: DC 12, one creature the pirate can see within 30 feet. Failure: The target has the Charmed condition until the start of the pirate’s next turn.


Pirate

Medium or Small Humanoid, Neutral
  • Armor Class 14
  • Hit Points 33 (6d8 + 6)
  • Speed 30 ft.
  • Initiative +5 (15)
STR
10 (0)
DEX
16 (3)
CON
12 (1)
INT
8 (-1)
WIS
12 (1)
CHA
14 (2)
  • Saving Throws Str +0, Dex +5, Con +1, Int -1, Wis +1, Cha +4
  • Senses passive Perception 11
  • Languages Common plus one other language
  • Challenge 1 (200 XP)
  • Habitat Any
  • Treasure Individual, Implements
  • Gear Daggers (6), Leather Armor

Actions


  • Multiattack. The pirate makes two Dagger attacks. It can replace one attack with a use of Enthralling Panache.
  • Dagger (Melee). Melee Weapon Attack: +5 to hit, reach 5 ft., One Target. Hit: (1d4 + 3) Piercing damage.
  • Dagger (Ranged). Ranged Weapon Attack: +5 to hit, reach 20/60 ft., One Target. Hit: (1d4 + 3) Piercing damage.
  • Enthralling Panache. *Wisdom Saving Throw:* DC 12, one creature the pirate can see within 30 feet. *Failure:* The target has the Charmed condition until the start of the pirate’s next turn.
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