Nefarious Parrot

Tiny beast, chaotic evil


  • Armor Class 13
  • Hit Points 2 (1d4)
  • Speed 5 ft., fly 30 ft.

STR DEX CON INT WIS CHA
2 (-4) 16 (+3) 10 (+0) 8 (-1) 12 (+1) 8 (-1)

  • Skills Deception +3
  • Senses passive Perception 11
  • Languages understands Common but only speaks through the use of its Mimicry trait.
  • Challenge 0 (10 XP)

Parrot Mimicry. The parrot can mimic any sounds it has heard, including voices. A creature that hears the sounds can tell they are imitations with a successful DC 13 Wisdom (Insight) check. The parrot typically uses this to replicate the sounds of combat to deter invaders.

Divulger of Secrets. The parrot tend to stick with the crew for extended periods of time and will often overhear private information. Roll a d20 to determine what information the parrot holds:

  • 1-5: No useful information.
  • 6-10: Non-relevant information, such as which port has the most beautiful barmaidens.
  • 11-15: A humiliating or shameful secret about the captain.
  • 16-18: The location of a valuable item belonging to the crew.
  • 19-20: The location of a treasure map that shows the location of the crew's full fortune.

Actions

Bite. Melee Weapon Attack: +0 to hit, reach 5ft., one target. Hit: 1 piercing damage.



Pirate Peon

Medium humanoid, neutral evil


  • Armor Class 13 (leather armor)
  • Hit Points 22 (4d8 + 4)
  • Speed 30 ft.

STR DEX CON INT WIS CHA
11 (+0) 15 (+2) 12 (+1) 10 (+0) 12 (+1) 7 (-2)

  • Skills Sleight of Hand +4
  • Senses passive Perception 11
  • Languages Common and one other language
  • Challenge 1/2 (100 XP)

Fierce Loyalty. Whenever an ally within 20 feet of the pirate drops to 0 hit points, the pirate can use its reaction to make a melee weapon attack or to move up to half its speed towards the enemy that killed their ally.

Sure-Footed. The pirate has advantage on Strength and Dexterity saving throws made against effects that would knock it prone.

Actions

Scimitar. Melee Weapon Attack: +4 to hit, reach 5ft., one target. Hit: 5 (1d6 + 2) slashing damage.

Dagger. Melee or Ranged Weapon Attack: +4 to hit, reach 5 ft. or range 20/60 ft., one target. Hit: 4 (1d4 + 2) piercing damage.


Corsair Cannoneer

Medium humanoid, neutral evil


  • Armor Class 16 (chain mail)
  • Hit Points 32 (5d8 + 10)
  • Speed 30 ft.

STR DEX CON INT WIS CHA
17 (+3) 10 (+0) 14 (+2) 10 (+0) 13 (+1) 9 (-1)

  • Skills Athletics +5
  • Senses passive Perception 11
  • Languages Common and one other language
  • Challenge 1 (200 XP)

Fierce Loyalty. Whenever an ally within 20 feet of the pirate drops to 0 hit points, the pirate can use its reaction to make a melee weapon attack or to move up to half its speed towards the enemy that killed their ally.

Sure-Footed. The pirate has advantage on Strength and Dexterity saving throws made against effects that would knock it prone.

Actions

Maul. Melee Weapon Attack: +5 to hit, reach 5ft., one target. Hit: 10 (2d6 + 3) bludgeoning damage.

Handheld Cannon (Recharge 4-6). Ranged Weapon Attack: +5 to hit, range 20/60 ft., one target. Hit: 13 (4d4 + 3) bludgeoning damage.



Seaside Sorcerer

Medium humanoid, neutral evil


  • Armor Class 11 (14 with mage armor)
  • Hit Points 44 (8d8 + 8)
  • Speed 30 ft.

STR DEX CON INT WIS CHA
8 (-1) 14 (+2) 12 (+1) 9 (-1) 10 (+0) 15 (+2)

  • Saving Throws Cha +4, Con +3
  • Skills Athletics +1, Persuasion +4
  • Senses passive Perception 10
  • Languages Common and one other language
  • Challenge 2 (450 XP)

Spellcasting. The Sorcerer is a 4th-level spellcaster. Its spellcasting ability is Charisma (spell save DC 12, +4 to hit with spell attacks). It has the following sorcerer spells prepared:

Cantrips (at will): control water, gust, shocking grasp

1st level (4 slots): fog cloud, mage armor, witch bolt

2nd level (3 slots): misty step, phantasmal force

Sorcerery Points. The sorcerer has 4 sorcery points. It can spend 1 or more sorcery points as a bonus action to gain one of the following benefits:

  • Distance Spell: When the sorcerer casts a spell that has a range of 5 feet or greater, it can spend 1 sorcery point to double the range of that spell.

  • Subtle Spell: Whe the sorcerer casts a spell, it can spend 1 sorcery point to cast the spell without any somatic or verbal components.

Actions

Dagger. Melee or Ranged Weapon Attack: +4 to hit, reach 5 ft. or range 20/60 ft., one target. Hit: 4 (1d4 + 2) piercing damage.


Ogre Pirate

Large giant, neutral evil


  • Armor Class 14 (studded leather, shield)
  • Hit Points 76 (9d10 + 27)
  • Speed 40 ft.

STR DEX CON INT WIS CHA
19 (+4) 10 (+0) 17 (+3) 5 (-3) 8 (-1) 8 (-1)

  • Senses darkvision 60ft., passive Perception 9
  • Languages Common, Giant
  • Challenge 3 (700 XP)

Limited Vision. The ogre wears an eye patch in an attempt to blend in with its fellow pirates. This causes some issues with depth perception which the ogre attempts to overcome with brute strength. The ogre makes all ranged attacks at disadvantage but also deals double its strength modifier damage on those attacks.


Actions

Giant Fish. Melee Weapon Attack: +6 to hit, reach 5ft., one target. Hit: 11 (2d6 + 4) bludgeoning damage and the target must succeed on a DC 14 Strength saving throw or drop whatever it is holding at its feet. Picking up a fish oil covered item requires an action or bonus action and success on a DC 12 Dexterity (Sleight of Hand) to get a solid grip, otherwise it slips out of their hands and drops to the ground again.

Cannon Ball. Ranged Weapon Attack: +6 to hit, range 30/90 ft., one target. Hit: 18 (3d6 + 8) bludgeoning damage.



Battle-Scarred Buccaneer

Medium humanoid, neutral evil


  • Armor Class 16 (breastplate)
  • Hit Points 84 (13d8 + 26)
  • Speed 35 ft.

STR DEX CON INT WIS CHA
14 (+2) 18 (+4) 15 (+2) 10 (+0) 15 (+2) 13 (+1)

  • Skills Perception +4, Persuasion +3
  • Senses passive Perception 14
  • Languages Common and two other languages
  • Challenge 4 (1,100 XP)

Fierce Loyalty. Whenever an ally within 20 feet of the buccaneer drops to 0 hit points, the buccaneer can use its reaction to make a melee weapon attack or to move up to half its speed towards the enemy that killed their ally.

Sure-Footed. The pirate has advantage on Strength and Dexterity saving throws made against effects that would knock it prone.

Combat Expertise. The pirate scores a critical hit on a roll of 19-20.


Actions

Multiattack. The pirate makes two melee attacks or two ranged attacks.

Rapier. Melee Weapon Attack: +6 to hit, reach 5ft., one target. Hit: 8 (1d8 + 4) piercing damage.

Crossbow. Ranged Weapon Attack: +6 to hit, range 80/320 ft., one target. Hit: 18 (1d8 + 4) piercing damage.


Reactions

Drink Up! (1/Day). After being hit by an attack, the pirate can take a massive swig of rum, giving it reinvigorated combat vitality at the cost of accuracy. The pirate gains 25 temporary hit points, but makes all attacks for the rest of combat with a with a +3 to its attack bonus rather than +6.



Pirate Captain

Medium humanoid, neutral evil


  • Armor Class 16 (studded leather)
  • Hit Points 104 (16d8 + 32)
  • Speed 35 ft.

STR DEX CON INT WIS CHA
12 (+1) 18 (+4) 14 (+2) 14 (+2) 11 (+0) 15 (+2)

  • Saving Throws Dex +7, Int +5
  • Skills Acrobatics +7, Deception +5, Insight +3, Persuasion +5
  • Senses passive Perception 10
  • Languages Common and two other languages
  • Challenge 6 (2,300 XP)

Master Duelist. The captain ignores the loading property of pistols. Additionally, being within 5 feet of a hostile creature doesn't impose disadvantage on its ranged attack rolls.

Fleet-Footed. The pirate has advantage on Strength and Dexterity saving throws made against effects that would knock it prone and it can take the Dash or Disengage action as a bonus action on each of its turns.


Actions

Multiattack. The pirate makes two rapier attacks and one pistol attack, or makes two pistol attacks.

Rapier. Melee Weapon Attack: +7 to hit, reach 5ft., one target. Hit: 8 (1d8 + 4) piercing damage.

Pistol. Ranged Weapon Attack: +7 to hit, reach 30/90 ft., one target. Hit: 9 (1d10 + 4) piercing damage.

Fire at Will (Recharge 5-6). The pirate gives out a commanding shout to up to 3 allies within 60 feet that can hear it. Those allies may immediately use their reaction to make an attack against a target in range with advantage.

Legendary Actions

The pirate captain can take 3 legendary actions, choosing from the options below. It can take only one legendary action at a time and only at the end of another creature's turn. The pirate captain regains spent legendary actions at the start of its turn.

Fire! The captain makes a pistol attack.

Oil Flask. The captain throws a flask of oil at a location within 15 feet, causing a 5 foot square area to become incredibly slippery. A creature that enters this area or ends its turn there must succeed on a DC 13 Dexterity saving throw or fall prone.

Parley! (1/Day). The captain shouts out for combat to halt so he or she can strike a deal. Each hostile creature within 120 feet that can hear the captain must succeed on a DC 15 Wisdom saving throw or be magically charmed for the next 10 minutes. This effects ends if an agreement has been reached or if a charmed creature or one of its allies is damaged by the captain or one of its allies.