Pirate NPCs Art Credit

Pirates are a staple of high-seas adventures, bringing with Admiral's Order - Slawomir Maniak, Wizards of the Coast
them a mix of danger, charm, and lawlessness. Whether they Fathom Fleet Boarder - Sidharth Chaturvedi, Wizards of
are raiding coastal villages, battling naval fleets, or seeking the Coast
buried treasure, pirates add an element of unpredictable Brazen Blademaster - Jarel Threat, Wizards of the Coast
excitement to any campaign. In this section, you'll find a Swaggering Corsair - Scott Murphy, Wizards of the Coast
variety of pirate NPCs to challenge and engage your players, Dire Fleet Warmonger - Mathias Kollros, Wizards of the
from lowly crewmates to infamous pirate captains. Coast
Pirate NPCs can be found in a variety of settings, from Headstrong Brute - Yongjae Choi, Wizards of the Coast
bustling port towns to remote islands and even aboard Grasping Scoundrel - Steve Prescott, Wizards of the
ghostly ships that haunt the open seas. These NPCs bring Coast
with them not only the threat of combat but also Moby Dick - James Edwin McConnell
opportunities for diplomacy, espionage, and intrigue. Some Deadeye Quartermaster - Josh Hass, Wizards of the Coast
pirates might be ruthless and bloodthirsty, while others might Deadeye Plunderers - Greg Opalinski, Wizards of the
have a code of honor or a tragic backstory that reveals a more Coast
complex character. Dinosaur Hunter - Tianhua X, Wizards of the Coast
In this section, you'll find stat blocks and descriptions for a Broadside Bombardiers - Tomek Larek, Wizards of the
range of pirate NPCs, each with their own strengths, Coast
weaknesses, and unique abilities. For stat blocks with more Captain Ripley Vance - Mathias Kollros, Wizards of the
nuanced abilities, tactics are included to help you use the Coast
pirate effectively. Captivating Crew - Winona Nelson, Wizards of the Coast
Because pirates are known for their plundering, providing Entrancing Melody - Winona Nelson, Wizards of the Coast
them with loot from the individual treasure table in the DMG Ramirez DePietro, Pillager - Anna Steinbauer, Wizards of
can help reinforce this theme. You can load their ships up the Coast
with gems, art objects, or entire treasure hoards to drive Admiral Beckett Brass - Jason Rainville, Wizards of the
home how lucrative their raids can be. Coast
Pitiless Plunderer - David Palumbo, Wizards of the Coast

1
This is unofficial Fan Content permitted under the Fan Content Policy. Not approved/endorsed by Wizards. Portions of the materials used
are property of Wizards of the Coast. ©Wizards of the Coast LLC.
 Crew Members
Most ships are made up of general crew members who
Plunderer
possess basic seafaring skills and moderate proficiency with Medium humanoid (any race), any non-lawful
weapons. They are usually armed with muskets and alignment
cutlasses.
Plunderers. More dangerous and notorious crew Armor Class 15 (hide armor)
members are often referred to as plunderers. They make up Hit Points 33 (6d8+6)
the rank-and-file crew of experienced and deadly pirate crews Speed 30 ft., swim 20 ft., climb 20 ft.
and are known for their devastating raids.

Crew Member Tactics STR DEX CON INT WIS CHA

A crew member's musket takes a round to load and should 14 (+2) 14 (+2) 12 (+1) 10 (0) 10 (0) 12 (+1)
only be used if they can find total cover from ranged attacks
with no nearby melee attackers. Otherwise, the crew member
Skills Acrobatics +4, Intimidation +3
will draw their scimitar and charge. Senses passive Perception 10
Languages any two languages
Challenge 1 (200 XP) Proficiency Bonus +2

Crew Member Weapons Expert. The plunderer gets +1 to attack

Medium humanoid (any race), any non-lawful rolls it makes with weapons (included in the attack).
alignment
Defense. While the plunderer is wearing armor, it
gains a +1 bonus to AC (included in its AC).
Armor Class 13 (hide armor)
Hit Points 16 (3d8+3) Actions
Speed 30 ft., swim 20 ft., climb 20 ft.
Musket. Ranged Weapon Attack: +5 to hit, range
100/400 ft., one target. Hit: 15 (3d8 + 2) piercing
STR DEX CON INT WIS CHA damage. The plunderer can't make this attack again
with the weapon until it loads it as an action.
12 (+1) 12 (+1) 12 (+1) 10 (0) 10 (0) 12 (+1)
Rapier. Melee Weapon Attack: +5 to hit, reach 5 ft.,
Skills Acrobatics +3, Intimidation +3 one target. Hit: 6 (1d8 + 2) slashing damage.
Senses passive Perception 10
Languages any two languages
Challenge 1/4 (50 XP) Proficiency Bonus +2

Actions
Musket. Ranged Weapon Attack: +3 to hit, range
100/400 ft., one target. Hit: 14 (3d8 + 1) piercing
damage. The crew member can't make this attack
again with the weapon until it loads it as an action.
Rapier. Melee Weapon Attack: +3 to hit, reach 5 ft.,
one target. Hit: 5 (1d8 + 1) slashing damage.

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Duelists
Duelists are some of the most cocky members of a crew,
wielding a rapier and dagger with mastery in one-on-one
Duelist
Medium humanoid (any race), any non-lawful
combat. Some pirate captains may even have them act as
alignment
their champions in duels of honor.
Master Duelists. Few duelists survive enough
competitions to be called masters among their peers. Their Armor Class 14 (hide armor)
egos are only matched by their exquisite swordplay. Such
Hit Points 38 (7d8 + 7)
confidence allows them to force an enemy warrior into a duel
Speed 30 ft., swim 20 ft., climb 20 ft.
through sheer intimidation. They never refuse a challenge
from another swordsman, provided they believe their STR DEX CON INT WIS CHA
opponent has no intention of using underhanded tricks or
magic. 12 (+1) 14 (+2) 12 (+1) 10 (0) 12 (+1) 12 (+1)

Skills Acrobatics +4, Intimidation +3, Perception +3

Senses passive Perception 13
Languages any two languages
Challenge 2 (450 XP) Proficiency Bonus +2

Audacity (1/Turn). The duelist deals an extra 10

(3d6) damage when it hits a target with a weapon
attack and has advantage on the attack roll, or if it's
within 5 feet of it and no other creatures are within
5 feet of the duelist.
Rakish. The duelist adds its Charisma modifier to
initiative rolls and to damage rolls for its attacks
(included in the attack).

Actions
Multiattack. The duelist makes two attacks: one with
a dagger and one with its rapier.
Dagger. Melee or Ranged Weapon Attack: +4 to hit,
reach 5 ft. or range 30/120 ft., one target. Hit: 5
(1d4 + 3) piercing damage.
Rapier. Melee Weapon Attack: +4 to hit, reach 5 ft.,
one target. Hit: 7 (1d8 + 3) slashing damage.

Reactions
Uncanny Dodge. The duelist halves the damage that
it takes from an attack that hits it. The duelist must
be able to see the attacker.

3
 Master Duelist Actions
Medium humanoid (any race), any non-lawful alignment Multiattack. The duelist makes three attacks: one with a
dagger and two with its rapier. If all the attacks hit the
Armor Class 18 (studded leather armor) same creature, the creature drops an object of the
Hit Points 65 (10d8 + 20) duelist's choice. The object lands in an area of the
Speed 30 ft., swim 20 ft., climb 20 ft. duelist's choice that is within 10 feet of the creature.
Dagger. Melee or Ranged Weapon Attack: +4 to hit,
STR DEX CON INT WIS CHA reach 5 ft. or range 30/120 ft., one target. Hit: 8 (1d4 +
6) piercing damage.
12 (+1) 16 (+3) 12 (+1) 10 (+0) 14 (+2) 16 (+3)
Rapier. Melee Weapon Attack: +4 to hit, reach 5 ft., one
Saving Throws Wis +4 target. Hit: 10 (1d8 + 6) slashing damage.
Skills Acrobatics +7, Intimidation +5, Perception +4
Senses passive Perception 14
Bonus Actions
Languages any two languages Panache (Recharges after a Short or Long Rest). The
Challenge 4 (1,100 XP) Proficiency Bonus +2 duelist attempts to compel a creature into a duel. One
creature that it can see and that can hear the duelist
Audacity (1/Turn). The duelist deals an extra 17 (5d6) within 30 feet of it must make a DC 13 Charisma
damage when it hits a target if it's within 5 feet of it saving throw. On a failed save, the creature and the
and no other creatures are within 5 feet of the duelist. duelist are obsessed with each other for one minute.
While the duelist is obsessed, it has advantage on
Rakish. The duelist adds its Charisma modifier to attack rolls. The obsession ends if a creature friendly to
initiative rolls and to damage when it hits a target with the duelist damages the target or casts a harmful spell
a weapon attack and has advantage on the attack roll, or on it, or if the duelist ends its turn more than 30 feet
if it's within 5 feet of it and no other creatures are away from the target.
within 5 feet of the duelist.
Reactions
Suave Defense. While the duelist is wearing light or no
armor and wielding no shield, its AC includes its Uncanny Dodge. The duelist halves the damage that it
Charisma modifier. takes from an attack that hits it. The duelist must be
able to see the attacker.

New Condition: Obsessed

The creature becomes fixated on a creature or
object, which becomes a source of its obsession.
Being obsessed has the following effects on a
creature:
While the creature can see a source of its
obsession, it can't target any creature or object
with an attack, spell, or ability except for a
source of its obsession.
While the creature can see a source of its
obsession, it can't cast spells or use abilities
that target an area (such as the fireball spell)
unless a source of its obsession is in that area.
The creature can't willingly move away from a
source of its obsession.

4
Ship Boarders
Ship boarders are usually the most brash members of the Bloody Boot Boarders. Originally inspired by the crazed
crew, forgoing guns for melee combat. When a pirate ship rampage of the iron-footed red cap fey, these pirates adopted
closes in on another vessel, these warriors appear from amid similar adornments for the bottoms of their boots. Swinging
the gunsmoke, swinging in with legs outstretched and into battle lines like a battering ram, those knocked down
delivering rib-breaking kicks to anyone unfortunate enough to quickly have metal-spiked boots stamped into their faces.
be in their way. These pirates now join other crews for a steep cost that is
well worth the gold.

Ship Boarder Actions

Medium humanoid (any race), any non-lawful alignment Greataxe. Melee Weapon Attack: +4 to hit, reach 5 ft.,
one target. Hit: 9 (1d12 + 3) slashing damage.
Armor Class 14 (hide armor)
Hit Points 45 (7d8+14) Stomp Kick. Melee Weapon Attack: +4 to hit, reach 5 ft.,
Speed 30 ft., swim 20 ft., climb 30 ft. one target. Hit: 5 (1d6 + 2) bludgeoning damage. If the
boarder moved at least 20 feet straight toward the
target immediately before the hit, the target extra 7
STR DEX CON INT WIS CHA (2d6) bludgeoning damage and must succeed on a DC
13 Strength saving throw or be knocked prone and
14 (+2) 14 (+2) 14 (+2) 10 (0) 10 (0) 12 (+1) pushed up to 10 feet away.

Skills Acrobatics +4, Athletics +4, Intimidation +3 Bonus Actions

Senses passive Perception 10 Grappling Hook. The boarder throws a Grappling Hook
Languages any two languages at a mast, railing of a ship, or other protrusion within
Challenge 1 (200 XP) Proficiency Bonus +2 20 feet of it, hooking it. The hook remains attached
until a creature within reach of the hook uses its action
Rig Monkey. The boarder does not provoke attacks of to remove it, or 5 slashing damage is dealt to the tether
opportunity while climbing or swinging past a creature (AC 10).
on a rope.

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 Bloody Boot Boarder Actions
Medium humanoid (any race), any non-lawful alignment Multiattack. The boarder makes two attacks: one with its
Greataxe or Stomp Kick, and one with its Pulverizing
Armor Class 15 (studded leather) Stomp.
Hit Points 75 (10d8+30)
Speed 30 ft., swim 20 ft., climb 30 ft. Greataxe. Melee Weapon Attack: +5 to hit, reach 5 ft.,
one target. Hit: 16 (2d12 + 3) slashing damage.
Stomp Kick. Melee Weapon Attack: +5 to hit, reach 5 ft.,
STR DEX CON INT WIS CHA one target. Hit: 10 (2d6 + 3) bludgeoning damage. If
16 (+3) 16 (+3) 16 (+3) 10 (0) 10 (0) 12 (+1) the boarder moved at least 20 feet straight toward the
target immediately before the hit, the target takes an
Saving Throws Dex +5 extra 10 (3d6) bludgeoning damage and must succeed
Skills Acrobatics +5, Athletics +5, Intimidation +3 on a DC 14 Strength saving throw or be knocked prone
Senses passive Perception 10 and pushed up to 10 feet away.
Languages any two languages Pulverizing Stomp. Melee Weapon Attack: +5 to hit,
Challenge 3 (700 XP) Proficiency Bonus +2 reach 5 ft., one prone target. Hit: 13 (2d10 + 3)
bludgeoning damage. A prone creature cannot stand up
Brute. A melee weapon deals one extra die of its until the end of the boarder's next turn unless it uses all
damage when the boarder hits with it (included in the of its movement to make a DC 14 Constitution saving
attack). throw, standing up on a success.
Rig Monkey. The boarder does not provoke attacks of Bonus Actions
opportunity while climbing or swinging past a creature
on a rope. Grappling Hook. The boarder throws a grappling hook at
a mast, railing of a ship, or other protrusion within 20
feet of it, hooking it. The hook remains attached until a
creature within reach of the hook uses its action to
remove it, or 5 slashing damage is dealt to the tether
(AC 10).

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Bone Saws
Usually the most crude and sadistic members of the crew,
Bone Saws are armed with jagged blades that inflict terrible
Bone Saw
Medium humanoid (any race), any non-lawful
gashes upon impact. Even a hit to a non-vital area from these
alignment
weapons can lead to severe blood loss.
Filth Blades. Only the most twisted pirate crews allow
Filth Blades into their ranks. Their jagged weapons have Armor Class 14 (hide armor)
grooves that accumulate grime and rust. These unsanitary
Hit Points 32 (5d8+10)
implements tear into flesh, leaving large, infected wounds.
Speed 30 ft., swim 20 ft., climb 20 ft.
Even those who defeat these depraved warriors in battle
often succumb to their injuries. STR DEX CON INT WIS CHA
14 (+2) 14 (+2) 14 (+2) 10 (0) 10 (0) 10 (+0)

Skills Athletics +4, Intimidation +2, Perception +2

New Condition: Wounds Senses passive Perception 12
While most creatures are wounded in combat, in Languages any two languages
this context, the wound is a special form of injury Challenge 1/2 (100 XP) Proficiency Bonus +2
that causes severe bleeding over a short period of
time and only specialized attacks and effects can
cause wounds. A creature can suffer from multiple
Actions
wounds at once and at the end of its turn, a Jagged Blade. Melee Weapon Attack: +4 to hit, reach
wounded creature takes 2 (1d4) necrotic damage 5 ft., one target. Hit: 5 (1d6 + 2) slashing damage,
for every wound it has sustained. Only creatures and the target receives a wound.
with blood (or something equivalent to blood) can
suffer wounds. Wounds can be removed in the
following ways:
When a creature is healed, one wound is
removed for every 5 hit points of healing it Filth Blade
receives. Medium humanoid (any race), any non-lawful
A creature can expend one use of a healer's kit alignment
to remove two wounds from itself or another
creature. Armor Class 15 (hide armor)
A wounded creature, or another creature within
Hit Points 52 (8d8+16)
5 feet of it, can make a DC 10 Wisdom Speed 30 ft., swim 20 ft., climb 20 ft.
(Medicine) check as an action to remove one
wound on a success. For every 5 points by
which the check exceeds the DC, an additional STR DEX CON INT WIS CHA
wound is removed.
16 (+3) 14 (+2) 14 (+2) 10 (0) 10 (0) 12 (+1)

Saving Throws Con +4

Skills Athletics +5, Intimidation +2, Perception +2
Senses passive Perception 12
Languages any two languages
Challenge 1 (200 XP) Proficiency Bonus +2

Defense. While the Filth Blade is wearing armor, it

gains a +1 bonus to AC (included in its AC).

Actions
Jagged Filthy Blade. Melee Weapon Attack: +5 to hit,
reach 5 ft., one target. Hit: 6 (1d6 + 3) slashing
damage plus 7 (2d6) necrotic damage, and the
target receives a wound. The target must also
succeed on a DC 13 Constitution saving throw or
contract a disease. Until the disease is cured, the
target can’t regain hit points. At the end of each of
its turns, the target repeats the saving throw, ending
the disease on a successful one.

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 Sea Dogs
Sea dogs are highly skilled in using harpoons to hunt wild
sea beasts. They primarily earn their living through whaling
and fishing, though in desperate times, they may join pirate
crews. In combat, they are known for using their harpoons to
impale and reel foes in so their allies can close in for the kill.
Tide Hunters. Tide hunters are veterans in their
profession, having been part of crews that have hunted many
dangerous sea monsters to bring their corpses ashore for
high profit. When a tide hunter focuses on its quarry, it is
almost certain to be dragged out of the water.

Sea Dog Tactics

Sea dogs should focus on mobile, low-strength targets,
locking them down and dragging them away from their allies
so they can be surrounded by the sea dog's own allies.

Tug of War Contests

A tug-of-war contest is a special type of opposed Strength
check between two creatures on either end of a rope.
While you're holding or tethered to a rope that is also held
by or tethered to another creature no more than one size
larger than you, you can use the Attack action to make an
opposed Strength check against the other creature to try to
pull the rope towards yourself. If you're able to make multiple
attacks with the Attack action, this attack replaces one of
them.
If you are more than one size larger than the opposing
creature, you automatically win this contest. If the results of
both checks are higher than the rope's break DC, the rope
snaps.
If you win the contest and the rope doesn't snap, you can
pull the rope along with you as you move or pull it towards
yourself while standing still. If the opposing creature doesn't
drop the rope or is tethered to it, it will be pulled along as
though you are grappling it.
You can't engage in a tug-of-war contest using a hand that
is holding other objects (including other ropes).

New Condition: Tethered

If a creature is attached to a rope (such as via a
lasso, harpoon, or a secure tie), it is tethered to
that rope. Creatures immune to the grappled
condition can't be tethered.
Any creature that succeeds in a tug-of-war
contest against a tethered creature using the
attached rope is considered to be grappling it. The
tethered creature can end the grapple by
untethering itself, breaking the rope, or winning
another tug-of-war contest against the grappling
creature.

8
 Tide Hunter
Medium humanoid (any race), any non-lawful
alignment

Armor Class 16 (leather armor)

Hit Points 45 (6d8+18)
Speed 30 ft., swim 20 ft., climb 20 ft.

STR DEX CON INT WIS CHA

Sea Dog 16 (+3) 14 (+2) 16 (+3) 10 (0) 16 (+3) 12 (+1)
Medium humanoid (any race), any non-lawful
alignment
Saving Throws Str +5, Wis +5
Skills Athletics +4, Intimidation +3, Survival +5,
Armor Class 14 (hide armor) Perception +5
Hit Points 19 (3d8+6) Senses passive Perception 15
Speed 30 ft., swim 20 ft., climb 20 ft. Languages any two languages
Challenge 1 (200 XP) Proficiency Bonus +2
STR DEX CON INT WIS CHA
Combat Angler. If a creature is in water and the tide
14 (+2) 14 (+2) 14 (+2) 10 (0) 14 (+2) 12 (+1) hunter is out of the water, the tide hunter has
advantage on harpoon attacks against it and on
Skills Athletics +4, Intimidation +3, Perception +4, opposed checks made to prevent it from dragging
Survival +4 the tide hunter by its tether.
Senses passive Perception 14
Wisened. While the tide hunter is wearing light or no
Languages any two languages
armor and wielding no shield, its AC includes its
Challenge 1/4 (50 XP) Proficiency Bonus +2 Wisdom modifier (included in its AC).
Combat Angler. If a creature is in water and the sea Actions
dog is out of the water, the sea dog has advantage
on harpoon attacks against it and on opposed Harpoon. Melee or Ranged Weapon Attack: +5 to
checks made to prevent it from dragging the sea hit, reach 5 ft. or range 20/60 ft., one target. Hit: 7
dog by its tether. (1d8 + 3) piercing damage, and the creature is
tethered by the harpoon's rope. The tide hunter can
then immediately make a tug-of-war contest against
Actions the tethered creature (no action required.) The rope
Harpoon. Melee or Ranged Weapon Attack: +4 to can be cut by dealing 10 slashing damage to it (AC
hit, reach 5 ft. or range 20/60 ft., one target. Hit: 6 13), and it has a break DC of 13. Any creature within
(1d8 + 2) piercing damage, and the creature is 5 feet of the target can use an action to remove the
tethered by the harpoon's rope. The sea dog can harpoon. Doing so deals an additional 3 (1d6)
then immediately make a tug-of-war contest against weapon damage to the target. The tide hunter can
the tethered creature (no action required.) The rope only have one creature tethered at a time.
can be cut by dealing 5 slashing damage to it (AC
10), and it has a break DC of 10. Any creature within Bonus Actions
5 feet of the target can use an action to remove the Bounty. (Recharges after a Short or Long Rest) The
harpoon. Doing so deals an additional 3 (1d6) Tide Hunter marks a creature that it can see for the
weapon damage to the target. The sea dog can only next minute. The first time on each of its turns it
have one creature tethered at a time. hits, it deals an additional 7 (2d6) damage.

9
This is unofficial Fan Content permitted under the Fan Content Policy. Not approved/endorsed by Wizards. Portions of the materials used
are property of Wizards of the Coast. ©Wizards of the Coast LLC.
 Powderhands
Crew members renowned for their skill with pistols are
known as powderhands due to the constant presence of black
Powderhand Scoundrel
Medium humanoid (any race), any non-lawful
powder residue between their fingers. They carry a bandolier
alignment
of pistols and can draw them at an alarming rate, unleashing
a volley of shots as they close the distance between them and
their short-lived targets. Armor Class 15 (studded leather armor)
Powderhand Scoundrels. Powderhand scoundrels are
Hit Points 55 (10d8+10)
master skirmishers, quick with both wit and reflexes. They
Speed 30 ft., swim 20 ft. climb 20 ft.
can unleash a volley of bullets and a blur of sword flashes
before an enemy can even draw their weapon. STR DEX CON INT WIS CHA
Powderhand Tactics 12 (+1) 16 (+3) 12 (+1) 12 (+1) 12 (+1) 16 (+3)
In an optimal situation, a powderhand should move within 10
feet of a target and then back up as far as it can. Another trick Saving Throws Int +3
is that if a powderhand is locked in melee combat, it can still Skills Acrobatics +5, Intimidation +5 Perception + 3
shoot another target that is 10 feet away, negating the Senses passive Perception 13.
disadvantage of being within 5 feet of a creature. Languages any two languages
Challenge 3 (700 XP) Proficiency Bonus +2

Rakish The powderhand adds its Charisma modifier

Powderhand to initiative rolls and to damage rolls for its attacks
(included in the attack).
Medium humanoid (any race), any non-lawful
alignment Quick Draw The scoundrel can draw a weapon as
part of the attack it makes with the weapon.
Armor Class 14 (hide armor) Fancy Footwork When the powderhand makes a
Hit Points 33 (6d8+6) melee attack against a creature, that creature can't
Speed 30 ft., swim 20 ft., climb 20 ft. make opportunity attacks against the powder hand
for the rest of the turn.
STR DEX CON INT WIS CHA Point Blank The powderhand has advantage on
ranged attack rolls against creatures within 10 feet
12 (+1) 14 (+2) 12 (+1) 10 (0) 12 (+1) 12 (+1)
of it.
Skills Acrobatics +4, Intimidation +3, Perception +3 Actions
Senses passive Perception 13
Multiattack. The scoundrel makes two attacks.
Languages any two languages
Challenge 1 (200 XP) Proficiency Bonus +2 Scimitar. Melee Weapon Attack: +5 to hit, reach 5
ft., one target. Hit: 9 (1d6 + 6) slashing damage.
Point Blank. The powderhand has advantage on
ranged attack rolls against a creature within 10 feet Pistol. Ranged Weapon Attack: +5 to hit, range
of it. 30/90 ft., one target. Hit: 13 (2d6 + 6) piercing
damage. The powderhand has four pistols; it can't
Quick Draw. The powderhand can draw a weapon as use a pistol again until it uses its action to load it or
part of the attack it makes with the weapon. in place of an attack that's part of an attack action.

Actions
Multiattack. The powderhand makes two attacks.
Pistol. Ranged Weapon Attack: +4 to hit, range
30/90 ft., one target. Hit: 9 (2d6 + 2) piercing
damage. The powderhand has four pistols; it can't
use a pistol again until it uses its action to load it or
in place of an attack that's part of an attack action.
Scimitar. Melee Weapon Attack: +4 to hit, reach 5
ft., one target. Hit: 5 (1d6 + 2) slashing damage.

10
Crackshots
The best marksmen of the crew are known as crackshots and
usually reside in the crow nests of a ship, where they have the
best vantage point. Crackshots eliminate the most valuable
targets of an opposing armada with deadly precision and are
greatly feared by those who normally try to stay out of direct
combat.
Trickshots. Trickshots are feared among sailors, and only
the most renowned and wealthy can afford their services.
What is most terrifying about these marksmen is their ability
to not only assassinate a target but also cause the same bullet
to ricochet and mortally wound or kill another unfortunate
soul standing nearby. Many loyal bodyguards have died in
vain, blocking a bullet from these sharpshooters, only to have
their charge be slaughtered by the same piece of lead.

Trickshot
Medium humanoid (any race), any non-lawful
Crackshot alignment
Medium humanoid (any race), any non-lawful
alignment Armor Class 16 (studded leather armor)
Hit Points 65 (10d8+20)
Armor Class 14 (leather armor) Speed 30 ft., swim 20 ft., climb 20 ft.
Hit Points 33 (6d8+6)
Speed 30 ft., swim 20 ft., climb 20 ft.
STR DEX CON INT WIS CHA
10 (0) 18 (+4) 14 (+2) 10 (0) 16 (+3) 12 (+1)
STR DEX CON INT WIS CHA
10 (0) 16 (+3) 12 (+1) 10 (0) 14 (+2) 12 (+1) Saving Throws Wis +5
Skills Acrobatics +6, Intimidation +3, Perception +7
Skills Acrobatics +5, Intimidation +3, Perception +6 Senses passive Perception 16
Senses passive Perception 16 Languages any two languages
Languages any two languages Challenge 3 (700 XP) Proficiency Bonus +2
Challenge 1 (200 XP) Proficiency Bonus +2
Ricochet Shot (1/turn). The trickshot deals an extra
Far Shot (1/turn). The crackshot deals an extra 9 18 (4d8) damage when it hits a target with a ranged
(2d8) damage when it hits a target with a ranged weapon attack if there are no creatures within 5 feet
weapon attack if there are no creatures within 5 feet of the trickshot when it made the attack. It then can
of the crackshot when it made the attack. cause the ammunition to ricochet toward a second
target within 10 feet of the first, making the same
Actions ranged attack with disadvantage against the second
target, this attack ignores half and three-quarters
Scimitar. Melee Weapon Attack: +5 to hit, reach 5 cover.
ft., one target. Hit: 6 (1d6 + 3) slashing damage.
Musket. Ranged Weapon Attack: +5 to hit, range Actions
100/400 ft., one target. Hit: 15 (3d8 + 3) piercing Multiattack. The trickshot makes two attacks.
damage. The crackshot can't make this attack again
with the weapon until it loads it as an action. Scimitar. Melee Weapon Attack: +6 to hit, reach 5
ft., one target. Hit: 7 (1d6 + 4) slashing damage.
Bonus Actions Musket. Ranged Weapon Attack: +6 to hit, range
Crosshairs. If the crackshot hasn't moved this turn, 100/400 ft., one target. Hit: 17 (3d8 + 4) piercing
its speed is reduced to 0 and it gains advantage on damage. The trickshot can't make this attack again
its next ranged attack roll this turn and ignores half with the weapon until it loads it as an action or in
and three-quarters cover. place of an attack that's part of an attack action.

Bonus Actions
Crosshairs. If the trickshot hasn't moved this turn, its
speed is reduced to 0 and it gains advantage on its
next ranged attack roll this turn and ignores half and
three-quarters cover.

11
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 Bombardiers
Bombardiers carry small mortar devices that can be loaded Storm Bombardier Tactics
with various types of rounds, such as grenades, sprays of
Storm bombardiers primarily use their lightning grenades,
shrapnel, or heavy lead slugs. When a Bombardier assaults a
aiming to hit as many targets as possible. They are also
vessel, it will be left in tatters.
willing to target a single enemy with low dexterity if a
Storm Bombardiers. Some Bombardiers are trained lightning grenade is already loaded. When multiple enemies
artificers, infusing their mortar rounds with thunder and are within melee range, they switch to using their thunder
lightning. When a Storm Bombardier engages in naval buster. If opponents are spread out, they will use their
combat, the opposing ships are torn apart in a wave of
thunder slug.
booming thunder and crackling electricity.

Bombardier Actions
Medium humanoid (any race), any non-lawful alignment Load. The Bombardier loads its mortar with one of the
following types of ammo, then must use another action
Armor Class 12 (hide armor) to fire the mortar to do one of the following:
Hit Points 32 (5d8+10)
Speed 30 ft., swim 20 ft., climb 20 ft. Mortar Slug. Ranged Weapon Attack: +5 to hit, range
80/240 ft., one target. Hit: 19 (3d10 + 3) piercing
damage.
STR DEX CON INT WIS CHA Mortar Grenade (3/day). The Bombardier launches a
14 (+2) 10 (+0) 12 (+1) 16 (+3) 12 (+1) 12 (+1) grenade up to 120 feet. Each creature within 20 feet
of the grenade's detonation must make a DC 13
Skills Intimidation +3, Perception +3 Dexterity saving throw, taking 18 (4d8) piercing
Senses passive Perception 13 damage on a failed save, or half as much damage on
Languages any two languages a successful one.
Challenge 2 (450 XP) Proficiency Bonus +2 Cabin Buster (3/day). The Bombardier uses its mortar to
create a shattering wave in a 30-foot cone. Each
Siege Weapon. The Bombardier deals double damage to creature in that area must make a DC 13 Dexterity
objects and structures with its mortar. saving throw, taking 18 (4d8) bludgeoning damage
on a failed save, or half as much damage on a
successful one.

12
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Storm Bombardier Thunder Slug. Ranged Weapon Attack: +6 to hit, range
80/240 ft., one target. Hit: 19 (3d10 + 3) piercing
Medium humanoid (any race), any non-lawful alignment
damage. The target becomes surrounded in
thunderous energy until the start of the Bombardier's
Armor Class 14 (ring mail) next turn. If the target willingly moves 5 feet or more
Hit Points 65 (10d8+20) before then, the target takes 16 (3d10) thunder
Speed 30 ft., swim 20 ft., climb 20 ft. damage, and the effect ends.
Lightning Grenade (3/day). The bombardier launches a
STR DEX CON INT WIS CHA grenade up to 120 feet. Each creature within 20 feet
of the grenade's detonation must make a DC 14
14 (+2) 10 (+0) 14 (+2) 18 (+4) 14 (+2) 12 (+1) Dexterity saving throw, taking 27 (6d8) lightning
damage on a failed save, or half as much damage on
Skills Intimidation +3, Perception +4 a successful one. If only one creature is in the area, it
Senses passive Perception 14 makes the saving throw with disadvantage.
Languages any two languages
Thunder Buster (3/day). The bombardier uses its mortar
Challenge 4 (1,100 XP) Proficiency Bonus +2
to create a shattering wave in a 30-foot cone. Each
creature in that area must make a DC 14
Siege Weapon. The bombardier deals double damage to Constitution saving throw. On a failed save, a
objects and structures with its mortar. creature takes 27 (6d8) thunder damage and is
pushed 15 feet away from the bombardier. On a
Actions successful save, the creature takes half as much
Load. The bombardier loads its mortar with one of the damage and isn’t pushed.
following types of ammo, then must use another action
to fire the mortar to do one of the following: Bonus Actions
Look Out. The bombardier takes the Search action.

13
 Shanty Bards
Lead Song Bards. Few sounds strike more fear in a
Many buccaneer crews are accompanied by bards to bolster
seafaring crew than the ship-shaking chorus of a Lead Song
the morale of the marauders. When approaching a vessel
Bard. Adept in both bardic magic and the use of firearms,
they wish to plunder, the bard begins "Vapouring," playing
they intensify their enchanted music with booming gunfire.
songs and chanting to boost the boldness of their fellow crew
Few men can maintain their resolve in the face of such a
members, riling them into a wild chorus. Opponents who
performance. If the opponent does not surrender
hear and see this rabble quickly lose their nerve and often
immediately, the bard delivers a flurry of bullets and biting
surrender before the fight even starts.
insults to prove that their fear was well placed.

Shanty Bard Actions

Medium humanoid (any race), any non-lawful alignment Spellcasting. The bard is a spellcaster. Its spellcasting
ability is Charisma (spell save DC 13, +5 to hit with
Armor Class 14 (hide) spell attacks). It knows the following spells:
Hit Points 52 (8d8+16)
Speed 30 ft., swim 20 ft., climb 20 ft. At will: message, vicious mockery
1st level (4 slots): healing word, dissonant whispers,
bane
STR DEX CON INT WIS CHA
2nd level (2 slots): shatter, lesser restoration
10 (+0) 14 (+2) 14 (+2) 10 (+0) 12 (+1) 16 (+3)
Scimitar. Melee Weapon Attack: +5 to hit, reach 5 ft.,
Saving Throws Dex +4, Cha +5 one target. Hit: 5 (1d6 + 2) slashing damage.
Skills Acrobatics +4, Intimidation +7, Performance +7 Vapouring Song (Recharges after a Short or Long Rest).
Senses passive Perception 11 The bard plays a song to rile up its allies into a
Languages any three languages frightening rabble. The bard and each of its allies within
Challenge 1 (200 XP) Proficiency Bonus +2 60 feet that can see and hear it gain 10 temporary hit
points for the next hour. Each other creature within
120 feet of the bard that can hear it must succeed on a
DC 13 Wisdom saving throw or be frightened of each
creature with temporary hit points from this feature for
the next hour.

14
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Lead Song Bard Spellcasting. The bard is a spellcaster. Its spellcasting
ability is Charisma (spell save DC 14, +6 to hit with
Medium humanoid (any race), any non-lawful alignment
spell attacks). It knows the following spells:

Armor Class 15 (studded leather) At will: message, vicious mockery (2d4)

Hit Points 65 (10d8+20) 1st level (4 slots): healing word, dissonant whispers,
Speed 30 ft., swim 20 ft., climb 20 ft. bane
2nd level (3 slots): shatter, lesser restoration
STR DEX CON INT WIS CHA 3rd level (2 slots): slow, mass healing word
10 (+0) 16 (+3) 14 (+2) 10 (+0) 12 (+1) 18 (+4) Pistol. Ranged Weapon Attack: +5 to hit, range 30/90
ft., one target. Hit: 13 (2d6 + 3) piercing damage. The
Saving Throws Dex +5, Cha +6, Wis +3 Bard has four pistols; it can't use a pistol again until it
Skills Acrobatics +5, Intimidation +8, Performance +8 uses its action to load it or in place of an attack that's
Senses passive Perception 11 part of an attack action.
Languages any three languages Scimitar. Melee Weapon Attack: +5 to hit, reach 5 ft.,
Challenge 3 (700 XP) Proficiency Bonus +2 one target. Hit: 5 (1d6 + 2) slashing damage.
Quick Draw. The bard can draw a weapon as part of the Vapouring Song (Recharges after a Short or Long Rest).
attack it makes with the weapon. The bard plays a song to rile up its allies into a
frightening rabble. The bard and each of its allies within
Ruthless. The bard has advantage on weapon attacks if 60 feet that can see and hear it gain 10 temporary hit
the target is frightened. points for the next hour. Each other creature within
120 feet of the bard that can hear it must succeed on a
Actions DC 14 Wisdom saving throw or be frightened of each
Multiattack. The bard makes two attacks. The bard can creature with temporary hit points from this feature for
cast one of its cantrips or use its Vapouring Song in the next hour.
place of one of those attacks.

15
 Pirate Captains
The captain commands a ship of pirates
and maintains the loyalty of his lawless
buccaneers through bravado, cunning, and
audacity, as captains who fail to exhibit
these traits quickly lose their high position.
Captains are not only cunning strategists
and usually the best warriors among the
crew but also possess a presence that drives
their crew to fearless daring, causing foes to
lose their resolve and surrender.

Captain Tactics
Captains typically use their Warning Shot
ability before their All Aboard so that the
frightened targets can be pelted with
gunfire and left unable to get closer.
If the captain's forces are primarily
melee-focused and the opponent has a lot
of ranged attackers, it will use its All Aboard
ability first instead. Once a captain is out of
ammo, it will charge in if it has allies to help
it utilize its Opportunist reaction.

Pirate Captain Actions

Medium humanoid (any race), any non-lawful alignment Multiattack. The captain makes two attacks.

Armor Class 14 (hide armor) Pistol. Ranged Weapon Attack: +4 to hit, range 30/90
Hit Points 78 (12d8+24) ft., one target. Hit: 11 (2d6 + 4) piercing damage. The
Speed 30 ft., swim 20 ft., climb 30 ft. captain has four pistols; it can't use a pistol again until
it uses its action to load it.
Rapier. Melee Weapon Attack: +4 to hit, reach 5 ft., one
STR DEX CON INT WIS CHA target. Hit: 8 (1d8 + 4) slashing damage.
14 (+2) 14 (+2) 14 (+2) 12 (+1) 12 (+1) 14 (+2) Warning Shot! (1/Day). The captain and each creature of
its choice that is within 60 feet of it that can hear it
Saving Throws Wis +3, Int +2 make a ranged weapon attack with disadvantage as a
Skills Athletics +4, Insight +3, Intimidation +4, reaction. Each creature attacked this way must succeed
Investigation +3, Perception +3 on a DC 12 Wisdom saving throw or be frightened of
Senses passive Perception 13 the captain for one minute. A frightened target can
Languages any two languages repeat the saving throw at the end of each of its turns,
Challenge 2 (450 XP) Proficiency Bonus +2 ending the effect on itself on a success.

Indomitable (1/day). The captain rerolls a failed saving Bonus Actions

throw. All Aboard! (1/Day). The captain and each creature of its
Quick Draw. The captain can draw a weapon as part of choice that is within 60 feet of it that can hear the
captain can immediately use its reaction to move up to
the attack it makes with the weapon.
its speed toward a hostile creature that it can see or
Rakish. The captain adds its Charisma modifier to reload a weapon.
initiative rolls and to damage rolls for its attacks
(included in the attack). Reactions
Opportunist. Whenever a creature within 5 feet of the
captain is hit by an attack made by a creature other than
it, the captain can make a melee weapon attack against
that creature.

16
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Pirate Admirals Pirate Kings/Queens
Pirate admirals are usually in charge of several ships of Pirate Kings and Queens are quite rare, typically rising from
buccaneers. This is no easy task, considering the unruly the ranks of seafaring marauders only once in a lifetime. To
nature of buccaneers. Pirate admirals are artful strategists earn such an unparalleled title, a pirate must command a vast
able to seize any weakness that presents itself within their armada of ships and perform infamous deeds. Pirate Kings
adversaries. and Queens of the past have commanded fleets powerful
enough to rival those of the nations they plundered. Indeed,
Pirate Admiral Tactics many kingdoms have been toppled or brought to the brink by
Pirate admirals differ from captains by having Sneak Attack such hordes.
and Raise Morale abilities. They are reliant on their minions
to help them consistently gain an advantage. Pirate King/Queen Tactics
Pirate kings & queens use the same tactics as admirals,
except they can gain advantage from their Ruthless ability to
trigger sneak attacks.

Pirate Admiral Sneak Attack (1/Turn). The admiral deals an extra 10

(3d6) damage when it hits a target with a weapon
Medium humanoid (any race), any non-lawful alignment
attack and has advantage on the attack roll, or when the
target is within 5 feet of an ally of the admiral that isn't
Armor Class 15 (studded leather) incapacitated and the admiral doesn't have
Hit Points 97 (13d8+39) disadvantage on the attack roll.
Speed 30 ft., swim 20 ft., climb 20 ft.
Actions
STR DEX CON INT WIS CHA Multiattack. The admiral makes two attacks.

16 (+3) 16 (+3) 16 (+3) 14 (+2) 14 (+2) 16 (+3) Fire at Will! (1/Day). The admiral and each creature of its
choice that is within 60 feet of it that can hear it make
Saving Throws Dex +6, Wis +5, Int +5 a ranged weapon attack as a reaction. Each creature
Skills Athletics +6, Insight +5, Intimidation +6, attacked this way must succeed on a DC 14 Wisdom
saving throw or be frightened of the admiral for one
Investigation +5, Perception +5
Senses passive Perception 15 minute. A frightened target can repeat the saving throw
Languages any three languages at the end of each of its turns, ending the effect on
Challenge 5 (1,800 XP) Proficiency Bonus +3 itself on a success.
Pistol. Ranged Weapon Attack: +6 to hit, range 30/90
Indomitable (2/day). The admiral rerolls a failed saving ft., one target. Hit: 13 (2d6 + 6) piercing damage. The
throw. admiral has four pistols; it can't use a pistol again until
it uses its action to load it.
Quick Draw. The admiral can draw a weapon as part of
the attack it makes with the weapon. Rapier. Melee Weapon Attack: +6 to hit, reach 5 ft., one
target. Hit: 10 (1d8 + 6) slashing damage.
Raise Morale. When the admiral hits a creature with a
weapon attack, another creature of the admiral's choice Bonus Actions
within 60 feet that can see and hear it gains advantage
All Aboard! (1/Day). The admiral and each creature of its
on all saving throws until the end of its next turn.
choice that is within 60 feet of it that can hear the
Rakish. The admiral adds its Charisma modifier to admiral can immediately use its reaction to move up to
initiative rolls and to damage rolls for its attacks its speed toward a hostile creature that it can see or
(included in the attack). use an object action.
Reactions
Opportunist. Whenever a creature within 5 feet of the
admiral is hit by an attack made by a creature other
than it, the admiral can make a melee weapon attack
against that creature.

17
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 Pirate King/Queen Sneak Attack (1/Turn). The king/queen deals an extra 21
(6d6) damage when it hits a target with a weapon
Medium humanoid (any race), any non-lawful alignment
attack and has advantage on the attack roll, or when the
target is within 5 feet of an ally of the king/queen that
Armor Class 16 (studded leather) isn't incapacitated and the king/queen doesn't have
Hit Points 190 (20d8+80) disadvantage on the attack roll.
Speed 30 ft., swim 20 ft., climb 20 ft.
Actions
STR DEX CON INT WIS CHA Multiattack. The king/queen makes two attacks.

16 (+3) 18 (+4) 18 (+4) 16 (+3) 14 (+2) 20 (+5) Pistol. Ranged Weapon Attack: +8 to hit, range 30/90
ft., one target. Hit: 16 (2d6 + 9) piercing damage. The
Saving Throws Str +7, Dex +8, Wis +6, Int +7 king/queen has four pistols; it can't use a pistol again
Skills Athletics +7, Insight +6, Intimidation +9, until it uses its action to load it.
Investigation +7, Perception +6 Rapier. Melee Weapon Attack: +8 to hit, reach 5 ft., one
Senses passive Perception 16 target. Hit: 13 (1d8 + 9) slashing damage.
Languages any four languages
Hit 'Em All! (1/Day). The king/queen and each creature
Challenge 10 (5,900 XP) Proficiency Bonus +4
of its choice that is within 60 feet of it that can hear it
make a ranged weapon attack with advantage as a
Indomitable (3/day). The king/queen rerolls a failed reaction. Each creature attacked this way must succeed
saving throw. on a DC 17 Wisdom saving throw or be frightened of
Quick Draw. The king/queen can draw a weapon as part the king/queen for one minute. A frightened target can
of the attack it makes with the weapon. repeat the saving throw at the end of each of its turns,
ending the effect on itself on a success.
Rakish. The king/queen adds its Charisma modifier to
initiative rolls and to damage rolls for its attacks Bonus Actions
(included in the attack).
Break the Bilges! (1/Day). The king/queen and each
Raise Morale. When the king/queen hits a creature with creature of its choice that is within 60 feet of it that
a weapon attack, another creature of the king/queen's can hear the king/queen can immediately use its
choice within 60 feet that can see and hear it gains reaction to move up to its speed toward a hostile
advantage on all saving throws until the end of its next creature and then make one weapon attack against it.
turn.
Reactions
Ruthless. The king/queen has advantage on weapon
attacks if the target is frightened. Opportunist. Whenever a creature within 5 feet of the
king/queen is hit by an attack made by a creature other
than it, the King/Queen can make a melee weapon
attack against that creature.

18
Pirate Loot CR 4 Pirate Loot Table
If you wish to add loot carried by pirates that varies based on 1d20 Loot
their CR, you can use the following tables in place of the ones
1-2 5gp
found in the DMG. You can have the pirates carry coin, gems,
or art objects they've stolen during their plunders. 3-6 1d4(2) x 5gp

CR 1/4 Pirate Loot Table 7-13 10gp

1d20 Loot 14-19 1d4(2) x 10gp
1-5 1d4(2) x 5sp 20 1d4(2) x 20gp
6-14 1d6(3) x 5sp
CR 5 Pirate Loot Table
15-20 2d4(5) x 5sp 1d20 Loot

CR 1/2 Pirate Loot Table 1-2 1d4(2) x 10gp

1d20 Loot 3-6 1d6(3) x 10gp
1-2 1d6(3) x 5sp 7-13 1d4(2) x 20gp
3-6 2d4(5) x 5sp 14-17 1d6(3) x 20gp
7-13 1d4(2) x 1gp 28-20 2d4(5) x 20gp
14-18 1d6(3) x 1gp
CR 10 Pirate Loot Table
19-20 2d4(5) x 1gp 1d20 Loot

CR 1 Pirate Loot Table 1 1d4(2) x 50gp

1d20 Loot 2-7 1d6(3) x 100gp
1-2 1d6(3) x 5sp 8-12 1d4(2) x 200gp
3-6 2d4(5) x 5sp 13-15 500gp
7-13 1d6(3) x 1gp 16-20 1,000gp
14-18 1d6(3) x 2gp
19-20 2d4(5) x 2gp

CR 2 Pirate Loot Table

1d20 Loot
1 1d4(2) x 1gp
2-6 1d6(3) x 1gp
7-13 2d4(5) x 1gp
14-19 2d4(5) x 2gp
20 2d6(3) x 2gp

CR 3 Pirate Loot Table

1d20 Loot
1-3 5gp
4-15 1d4(2) x 5gp
16-19 10gp
20 1d4(2) x 10gp

19
Change Log
1.0.0
Document release

Revision Numbers
Crew Member 1.0.0
Plunderer 1.0.0
Duelist 1.0.0
Master Duelist 1.0.0
Ship Boarder 1.0.0
Bloody Boot Boarder 1.0.0
Bone Saw 1.0.0
Filth Blade 1.0.0
Sea Dog 1.0.0
Tide Hunter 1.0.0
Powderhand 1.0.0
Powderhand Scoundrel 1.0.0
Crackshot 1.0.0
Trickshot 1.0.0
Bombardier 1.0.0
Storm Bombardier 1.0.0
Shanty Bard 1.0.0
Lead Song Bard 1.0.0
Pirate Captain 1.0.0
Pirate Admiral 1.0.0
Pirate King/Queen 1.0.0

Referenced Conditions
Obsessed 1.0.0
Wounds 1.0.0
Tethered 1.0.0

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are property of Wizards of the Coast. ©Wizards of the Coast LLC.