The pirate, the deadly but charismatic rogue, the truest form of the murdering gold hoarding character every cutpurse and highway robber sees when they look at their own reflection.

You are the living embodiement of the freedom and carelessness of the rogue. Travelling from place to place, swashbuckling, stealing, drinking and romancing in every town, port or dungeon you pass by. Fuelled by your own storied sense of self and a fierce desire to proove yourself through battle and riches, you will stop at nothing to become the greatest dread pirate the seas (or skies) have every known.

 

Rogue (Pirate) subclass table

Level	Proficiency Bonus	Sneak Attack	Features
3rd	+2	2d6	Roguish Archetype Dirty fighter, Skilled Privateer
9th	+4	5d6	Roguish Archetype Feature , Intimidating and audacious
13th	+5	7d6	Roguish Archetype Feature, An eye for valuables
17th	+6	9d6	Roguish Archetype Feature  Dread Pirate

Skilled Privateer

Your career on the seas  has added a selection of unique skills to your toolset. 

When you choose this archetype at 3rd level

You gain proficiency With pistols (p. 268 DMG) in addition this weapon has the characteristic light when wielding a light weapon in your other hand with which you are proficient.
You gain proficiency in Vehicles (water) ,Navigators tools & intimidation.

 

Dirty fighter

 Chivalry and honour are for people who want to die politely, you would rather live to fight another day, you are not above a low blow in combat to get the upper hand.

Starting at 3rd level before you make a melee attack in combat you may use your bonus action to to trip, blind or somehow hinder your opponent giving you advantage on your next attack.  You do not need advantage to apply sneak attack damage if the target of your attack has already been hit by a spell or attack this round as long as you do not have disadvantage. 

Intimidating and audacious

Starting at 9th level you are eager to join the fight and show off your talents you may add your charisma bonus to you initiative rolls.

Whether it is scaring an opponent into surrender or simply impressing your shipmates with a well timed quip in battle you have masterred the art of killing as a form of performance. When you hit with an attack on a creature the same size as you or smaller you may use a bonus action to intimidate them, they gain disadvantage on attack rolls until your next turn.

An eye for Treasure

Starting at 13th level Your love of treasure and a long career creating your own horde have given you a good eye for identifying what might fetch a good price. Whenever you make an Intelligence (Investigation) or Wisdom (Insight) check pertaining to the value of an item, you are proficient in the check and add double your Proficiency Bonus to the roll.

Once per short rest you may identify an item as if casting the spell identify as a ritual without material components.

Dread Pirate

Starting at 17th level Your name strikes fear into common folk accross the realms and your name alone can win battles before you so much as draw your sword.

You also gain the ability to strike fear into the hearts of targets  before combat begins. In the first round of combat you may use an action to intimidate of enemies equal to 1 + your charisma modifier . These enemies must be able to speak at least one langue although you do not need to share a language with them. Targets must make a wisdom saving throw (DC = 8 + Proficiency + CHA) or be frightened of you for one minute.  A target that fails by 10 or more must spend its turns trying to move as far away from you as it can, and it can’t willingly move to a space within 30 feet of you. It also can’t take reactions. For its action, it can use only the Dash  action or try to escape from an effect that prevents it from moving. If there’s nowhere to move, the creature can use the dodge action.

If you are targeting creatures larger than your self each creature counts as 1 additional enemy for every size catagory  larger than your own. (e.g. if you are size medium a size large enemy counts as 2 enemies for calculating how many you can target, huge = 3 gargantuan = 4)

Improved intimidation

Your Ability to intimidate enemies  as part of ' Intimidating and audacious' can now target creatures up to 1 size larger than you.