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Melee 1D8

Pirate

Pirates are swashbuckling scoundrels that prowl the seas and cause mayhem. The life of a pirate is one of self indulgence, crime, and hijinks. The love of the sea flows deeply in every Pirate’s veins as well as their love of adventure and treasure. Every Pirate values their freedom above any material possession though definitely not more than their comrade’s freedom.

While Pirates are wild individually, they form legendary crews full of specialized individuals that can accomplish even outlandish tasks. These crews are a fairly strict hierarchy that brings together people from every walk of life in pursuit of the freedom of the Pirate life.

Every Pirate craves adventure. Even the wealthiest Pirate on the nicest beach would eventually desire to sail beyond the horizon to seek more thrills. Pirates play by their own rules in every scenario, they’ll save a village or defeat a demon, for the right price or if it sounds fun.

Quick Build

You can make a Pirate quickly by following these suggestions. First, put your highest ability score in DEX, followed by WIS. Second, choose the Sailor Background.

Class Features

Hit Points

Hit Dice: 1D8 per Pirate level

At 1st level: 8 + Your CON Modifier

At higher levels: 1D8 or 5 if lower than 5, + CON Modifier

Proficiencies

Armor
Light Armor and Shields
Weapons
Simple Weapons, Battleaxe, Greataxe, Longsword, Maul, Pike, Rapier, Scimitar, Short Sword, Trident, Hand Crossbow, Heavy Crossbow, Net, Musket, Pistol
Tools
Navigator’s Tools, One Gaming Set
Saving Throws
DEX, WIS
Skills
Choose two from: Acrobatics, Athletics, Intimidation, Insight, Nature, Persuasion, or Survival

Starting Equipment

  • 1. (a) rapier or scimitar or (b) any simple melee weapon
  • 2. (a) cloth armor, light crossbow and 20 bolts or (b) leather armor, two daggers
  • 3. Explorer’s Pack
Position Feature
Cabin BoyAn assistant to someone in a Prestigious Position, you have additional training and learn any combination of any two skills and/or languages.
MateWith your connections you have made it a step above the rest of the Novices. You gain proficiency with any one Tool or Vehicle.
MusicianEvery musician is respected and gets special treatment. You have proficiency with one instrument and Performance checks and have leniency with regards to most of The Codes.
Powder MonkeyExpendable? Yes. Respected? Mostly. Swiftly running in dangerous positions you have an additional 10 ft of movement.
SwabbieYou barely made it. But hey, it’s a start. Someone saw something special in you and let you join. Spending the most time on shifting decks became light footed. You can use your reaction to add half your WIS modifier (Minimum 1) rounded down to DEX saving throws before knowing the outcome of the save once per long rest.
Maneuver Effect
Unorthodox Dash- When you take the Dash action you can apply one of the following effects:Drunken Dash: You do not provoke attacks of opportunity with your unpredictable movements. Blatant Dash: You shout and make a commotion giving creatures a bonus to Sleight of Hand and Stealth checks equal to your WIS modifier (Minimum 1) within 60 ft of you. Padding Dash: Taking advantage of soft boots and a light step you can take a normal Stealth check while Dashing.
Aggressive Disengage- When you take the Disengage action you can apply one of the following effects:Bash and Disengage: You leave a parting gift when you Disengage, making an unarmed strike. Dirty Disengage: You trick, throw dirt, or otherwise undermine your opponent when you Disengage causing their next attack to be with disadvantage.
Wild Dodge- When you take the Dodge action you can apply one of the following effects:Tripping Dodge: Once while you are moving while taking the Dodge action you can force a target within 5 ft of you to make DEX save DC 8 + your DEX modifier (Minimum 1) + your Proficiency Bonus and on a failed save their movement speed is halved until the end of their next turn. Flailing Dodge: You make a scene dodging attacks causing attacks within 10 ft of you to have a penalty equal to your WIS modifier (Minimum 1).
Fearless Fall- When you fall more than 20 ft you can use your reaction to apply one of the following effects:Tuck and Tumble: If you have at least 10 ft of unoccupied space where you land you reduce the amount of fall damage by 2D10 + your DEX modifier (Minimum 1) (Damage cannot be reduced to less than 0 with this feature). Falling Attack: If you fall within 5 ft of a space occupied by a creature you can take the attack action dealing additional damage equal to your fall damage and your fall damage is reduced to 1D4 for every 10 ft you fell.
Brazen Help- When you take the Help action you can apply one of the following effects:Drink and Some Help: Lending a hand and a bottle you and the target you helped perform a task gain temporary hit points equal to your WIS modifier (Minimum 1) + your Proficiency Bonus. Savage Help: You jerk, hit, or otherwise provoke an enemy with an ally nearby. Your ally has advantage on the next attack on them with an increased Critical hit range of 2 (19-20), but the next attack on you has advantage until the start of your next turn.
Quirky Hide- When you take the Hide action you can apply one of the following effects:Swap and Hide: You make a Sleight of Hand check to swap a piece of your clothing with someone within 5 ft of you, allowing you to Hide in plain sight, the target must have the same or equivalent article of clothing on hand. If you have a change of clothes on hand you can use this feature without a target. Drunken Hide: You cover yourself a bit and place a bottle of booze next to you giving you advantage on the Stealth check to hide.
Foolhardy Leap- When you make a running or standing leap you can apply one of the following effects:Fearless Leap: You add an additional 10 ft to your long jump distance whether running or standing but fall Prone upon landing. Hell or High Water Leap: When push comes to shove you make it work. When you make an Acrobatics or Athletics check to make a jump you can use a reaction and gain advantage but take 1D6 Bludgeoning damage after the leap whether or not it was a success or failure.
Unconventional Parry- When you use a Parry reaction you can apply one of the following effects:Improvised Parry: You parry with an object lying within 5 ft of you, the suddenness of the maneuver gives you +3 to AC. If the attack is parried the object takes the damage you would have taken, usually breaking the object. Acrobatic Parry: If you moved more than 10 ft your previous turn you can skillfully parry using your momentum giving you +4 to AC.
Position Feature
First MateThe highest a veteran can get before earning some prestige. You gain the Observant or Skill Expert feat through additional training.
GunnerYour marksmanship has been noticed. You gain the Crossbow Expert or Gunner Feat, depending on what your DM allows.
NavigatorTrusted above most in the crew you have gained some trust. You have proficiency with Cartographer’s Tools and have learned three languages to keep up with foreign maps.
QuartermasterYour culinary skills have elevated your status. You gain the Chef Feat and Resistance to the Poisoned condition through trial and error to provide for the crew.
Sailing MasterQuick witted and dextrous, your talents are recognized. You have Expertise in Water Vehicles and gain a Climbing speed of 30 ft.
Reputation Effect
BackstabbingCreatures within your aura have a penalty to attacks on creatures other than you equal to your WIS modifier (Minimum 1) as they are distracted keeping an eye on you.
Black HeartedCreatures within your aura have a penalty to Performance and Persuasion checks equal to your WIS modifier (Minimum 1) as they are nervous around you.
Caulous SoulYou and creatures of your choice within your aura have Resistance to Psychic damage as your influence hardens their minds.
Crafty GeniusCreatures within your aura have a bonus to checks with their Tools through careful coaching cultivated from experience and hard work on your part.
Even HandedCreatures of your choice within your aura have a bonus to Intimidation and Persuasion checks equal to your WIS modifier (Minimum 1) as you coax the best and worst out of them.
Iron FistedCreatures of your choice within your aura have a bonus to STR based checks and saving throws equal to your WIS modifier (Minimum 1) as they fear retribution and put forth extra work.
Life of the PartyYou and creatures of your choice within your aura gain temporary hit points equal to your WIS modifier + your Proficiency Bonus after completing a long or short rest from a fun “rest” full of revelry.
Ornery as HellCreatures of your choice within your aura have a bonus to attacks equal to half your WIS modifier (Minimum 1) rounded down as they fight to not get on your bad side.
SuperstitiousCreatures of your choice within your aura have a bonus to WIS saving throws equal to your WIS modifier (Minimum 1) as you ward and warn them.
Position Feature
BoatswainLauded for your craftsmanship and quick thinking, you have proved your dependability and worth time and time again. You add your WIS modifier (Minimum 1) to all ability checks and gain proficiency with any combination of three Tools, weapons, or armor.
CaptainYour efforts have made you a leader after climbing to the top. Choose one ability score and you increase the maximum score by two and increase the chosen score by two.
DoctorTrusted with the wellbeing of many lives you are trained to save lives. You can cast the following spells without expending a spell slot: Cure Wounds 3/long rest, Lesser Restoration 2/long rest.
HelmsmanYour skill at the helm makes you invaluable as you are unflappable in almost every situation. You have Resistance to Psychic damage and have advantage on saving throws to see through Illusions and have Resistance to being Frightened.
Master of ArmsEveryone depends on you. Trusted even above the Captain you are a treasure trove of skill and fighting ability. You are proficient in Martial Weapons and all Armor and can use the Armor Mastery properties of one type of armor and can use the Weapon Mastery properties of two more weapons.

Class Features

Lv 1

Sea Legs

The rough sea has trained your core and balance. Difficult Terrain cannot reduce to speed by more than 10 ft.

Novice Position

Every Pirate has to start somewhere. Choose from among the following positions to determine your position in the crew. You maintain the features of every position you hold.

Daring Maneuver

Acts of risk and leaps of faith are the bread and butter of Pirates. You have mastered many ways to evade enemies and use unusual situations to your advantage. You can use Daring Maneuvers times per long or short rest equal to your DEX modifier (Minimum 1).

You learn two Daring Maneuvers and can practice them during a long rest allowing you two switch which ones you can use.

Lv 2

Fighting Style

You adopt a particular style of fighting as your specialty. You can't take the same Fighting Style option more than once, even if you later get to choose again.

Weapon Mastery

Your practice has made you an elite among weapon wielders. You can use the mastery properties of two weapons of your choice.

Familiar

You gained a faithful companion. You can cast the spell Find Familiar without expending a spell slot once per long or short rest choosing from the following options

Parrot (Raven Stat Block), Iguana (Lizard), Monkey (Baboon)

Lv 3

Pirate Archetype

Your adventures have changed you fundamentally and given rise to a new power that sets you apart from other pirates. Your experience gives you features at levels 3, 6, 15, and 20.

Brine Madness

Conquistador

Cult of Calypso

Davy Jones' Crew

Eques Testudo (Turtle Knight)

Heavenly Navigator

Herald of the Devil Fish

Luck Keeper

Portrazers

→ Choose your subclass below

Underwater Combat

Just because you’re a little wet doesn’t mean the fight stops. You attack normally with non ranged melee and unarmed strikes while underwater even if you do not have a swimming speed. You can hold your breath a minimum amount of time equal to twice your CON modifier (Minimum 1) in minutes.

Lv 4

Ability Score Increase

You can increase one ability score of your choice by 2, or you can increase two ability scores of your choice by 1. As normal, you can't increase an ability score above 20 using this feature.

Additional Daring Maneuvers

You train and add another Daring Maneuver to your repertoire (Total 3).

Lv 5

Extra Attack

You train to attack with speed and ferocity. You can attack twice when you take the attack action.

Improvised Fighting

You have proficiency with improvised weapons through countless brawls. Improvised weapons have a damage die of 1D6 when used by you.

Swashbuckling

You are talented with the blade most weapons. The first time you deal damage with a melee attack or unarmed strike each turn you deal an additional 4 damage.

Lv 6
Lv 7

Veteran Position

You’ve put in the time and are moving up. Choose from among the following positions to determine your position in the crew. You maintain the features of every position you hold.

Suave Defense

You can deftly dodge in even dire circumstances using your wits and fancy footwork. You can use your reaction to launch a quip at a target attacking you within 5 ft, causing the attacker to attack with disadvantage.

You can use this feature times per long rest equal to your WIS modifier (Minimum 1).

Lv 8

Ability Score Increase

You can increase one ability score of your choice by 2, or you can increase two ability scores of your choice by 1. As normal, you can't increase an ability score above 20 using this feature.

Additional Daring Maneuvers

You train and add another Daring Maneuver to your repertoire (Total 4).

Lv 9

Persona

Your reputation and deeds have led to the creation of a fearsome persona, earning you a moniker. Monikers come in a wide range usually involving distinct physical features such as the classic Black Beard. With your persona you can add your WIS modifier (Minimum 1) to Intimidation and Persuasion checks.

Reputation

You have earned a reputation after your extended forays into piracy. Choose one of the following Reputations and gain the corresponding effect. Your Reputation creates an aura of effect that extends for 20 ft centered on you as you exert your presence. Any saving throws have a DC equal to your spell save DC.

There is a fifty percent chance at each new location that they have heard of you. If they have heard of you, you can use an action to gain advantage on Intimidation and Persuasion checks for one minute as you hype up your Reputation.

You can use this feature once per long or short rest.

Lv 10

Devil’s Luck

You seemed to be blessed by even the black hearted fiends in hell. You have the Lucky Feat and have 5 Luck Points as things just seem to work out as you go about your business.

Swashbuckling

Your talent with fighting grows. The first time you deal damage with a melee attack or unarmed strike each turn you deal an additional 6 damage.

Lv 11

Improved Improvised Fighting

You know how to use items around you to great effect. Improvised weapons have a damage die of 1D8 when used by you and have an attack range of 20/40 ft.

Lv 12

Ability Score Increase

You can increase one ability score of your choice by 2, or you can increase two ability scores of your choice by 1. As normal, you can't increase an ability score above 20 using this feature.

Additional Daring Maneuvers

You train and add another Daring Maneuver to your repertoire (Total 5).

Lv 13

Belay That!

Your quick thinking and leadership allows you to quickly correct others and lead them on a path of success. You can use your reaction to give a willing creature within 30 ft of you the benefit of the Dodge, Dash, or Disengage action if they choose to follow the order with a bonus action.

You can use this reaction to allow a willing target within 30 ft of you to reroll a Deception, Intimidation, or Persuasion check and take the new result, you must use this feature before knowing the outcome of the check.

You can use this feature times per long rest equal to your WIS modifier (Minimum 1).

Lv 14

Pirate Logic

You can choose to use your WIS modifier (Minimum 1) to INT or CHA based checks as people around you don’t really know how to deal with the way your phrase things and go about doing things.

Swashbuckling

You have become a true menace on the battlefield. The first time you deal damage with a melee attack or unarmed strike each turn you deal an additional 8 damage.

Lv 15
Lv 16

Ability Score Increase

You can increase one ability score of your choice by 2, or you can increase two ability scores of your choice by 1. As normal, you can't increase an ability score above 20 using this feature.

Additional Daring Maneuvers

You train and add another Daring Maneuver to your repertoire (Total 6).

Lv 17

Prestigious Position

You’ve topped the hierarchy, a master of your own domain among the crew. Choose from among the following positions to determine your position in the crew. You maintain the features of every position you hold.

Vicious Fighting

You know how to make an attack sting and use your skills to their best effect. Your critical hit range is increased to 19-20 and you deal additional damage on a critical hit equal to your DEX modifier (Minimum 1).

Lv 18

Pirate’s Life

You enjoy life to the fullest. The love of the sea and riotous living and bloody fighting fulfills you deeply. You gain the following features

Life at Sea: You have Resistance to Cold and Fire damage as the beating of the sun and the fury of storms has hardened you.

Love of Pleasure and Everything Else: If you roll on the Hedonist Table you roll twice and choose one or both of the results. You have twice your normal drinking capacity and resist the effects of drugs.

Rush of Battle: Once per long rest you can use an action to pump yourself up and get into the thrill of battle. For the next minute when you take the attack action you can make three attacks.

Lv 19

Epic Boon

You gain an Epic Boon feat for which you qualify.

Pirate Archetype

Pirate Subclasses (12)

Choose your subclass at the level indicated in the class table above.

Brine Madness A few very unfortunate Pirates come to encounter one too many horrors of the sea such as Sirens or Mermaids. These poor few have lost their minds but carry one with unflinching resolve. With the loss of their sanity… Conquistador Ruthless and single minded. Conquistadors are sent to destroy blasphemous groups and occult objects. Their primary objective is the profane Fountain of Youth. They eradicate all that oppose them with impunity. Strict… Cult of Calypso Sailing the sea under the protection of the goddess Calypso, a Cultist of Calypso embarks on missions from their dread goddess. Cultists of Calypso are granted powers over water and the arcane powers of the goddess to… Davy Jones’ Crew Having bargained their lives away to avoid Davy Jones’ Locker, the crew of the Flying Dutchman are cursed to sail forevermore. They aid their dread captain as they collect souls lost at sea and pass judgement. Feared… Eques Testudo (Turtle Knight) Each Eques Testudo or the Turtle Knight share the same story: they were saved and then made the champion of one of the few ancient Dragon Turtles who are known by the honorific of Testudo. Turtle Knights manage the… Heavenly Navigator Navigating the seas using the sun and stars is a burden true, but none bear it better than the Heavenly Navigators. They read the heavens and prepare rituals to channel the powers of the constellations. They receive… Herald of the Devil Fish The zealous followers of the Devil Fish who have been spared by the monster and made into servants. The Devil Fish is rumored to be an ancient and powerful Kraken but reports differ. Heralds of the Devil Fish are also… Luck Keeper Every (Good) ship and tavern has a Luck Keeper. One who keeps superstitions and tells omens. The Luck Keeper wards off bad luck and brings in good luck for the good of the ship and the crew. Highly respected with a… Portrazer Your run of the mill ruckus causing nuisances that infests the seedist of taverns through the coasts. Is what you think they might be. A Portrazer takes things to the extreme and then some. No drinking session is enough… Sea Scourge Under the direction of the nine Pirate Lords, Sea Scourges enforce the Pirate Codes and rain hell upon those that break The Codes. Brutal and devilishly efficient Sea Scourges are feared and respected in equal measure.… Thrice Afflicted All who dare sail into the Devil’s Triangle die and are cursed forevermore. They become the Thrice Afflicted, a curse for every point of the damned triangle. The Thrice Afflicted haunt the seas and bring misfortune and… Treasure Cursed Some treasures are better left alone. The Treasure Cursed have taken cursed gold and cannot rest until every piece of the treasure they took is returned and the blood debt is repaid. They take on a half life where the…