Comments from the Writer: We originally built this Fighter subclass for a pirate-themed softcover High Seas. Sailing, exploration and swashbuckling are staples of Dungeons & Dragons, so this was an easy pick for our player expansion Valda’s Spire of Secrets. This is the most up-to-date version, now as freely available as the original!
The wide-open ocean, the salty breeze, and the freedom of a ship—these are the things a corsair values more than anything else. Though an archetypal corsair is no less trained than their military counterparts, they prefer a more swashbuckling, charismatic approach to life, and take well to privateering, smuggling, exploring, and other self-directed work.
Bonus Proficiencies
When you choose this archetype at 3rd level, you gain proficiency in the Sleight of Hand skill, if you did not already have proficiency.
Surprise Attack
At 3rd level, you’ve learned to strike foes when they least expect it. Once per turn, you can deal an extra 1d6 damage to one creature you hit with an attack if you have advantage on the attack roll. The attack must use a finesse or a ranged weapon.
You don’t need advantage on the attack roll if another enemy of the target is within 5 feet of it, that enemy isn’t incapacitated, and you don’t have disadvantage on the attack roll.
The amount of extra damage increases as you gain levels in this class. At 7th level, this damage increases to 2d6, at 11th level, this damage increases to 3d6, and at 15th level, this damage increases to 4d6.
Commandeer
At 3rd level, you can replace one of your attacks with an attempt to steal an item being carried by another creature. You can’t attempt to steal an object that is being worn as clothing or armor, nor can you steal an object that is being held in one of the target’s hands. Make a Dexterity (Sleight of Hand) check, opposed by the target’s AC. On a success, you successfully steal that object. You must have a free hand to use this ability.
Three Sheets
Starting at 7th level, whenever you use your Second Wind ability, you can also take the Dash or Disengage action as part of the same bonus action.
Charmed Life
By 10th level, you can saunter into trouble and make it out unscathed, thanks to your considerable luck. You can gain advantage on one ability check, attack roll, or saving throw that uses Dexterity or Charisma.
Once you use this ability, you can’t use it again until you finish a short or long rest.
Slippery Positioning
Starting at 15th level, whenever a hostile creature that you can see within 60 feet moves, you can move 5 feet without using your reaction or provoking opportunity attacks. On each round, you can use this ability a number of times equal to your Dexterity modifier.
Untouchable Swordsman
By 18th level, you are legendary with a cutlass. Whenever you hit a creature with your Surprise Attack, the target has disadvantage on attack rolls against you until the start of your next turn.
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Flavorful and powerful! This subclass creates something that’s hard to do in 5e– a powerful Dex-based fighter who can chase the Great Weapon Fighters for damage. It also has some solid support abilities beyond damage, with good defensive abilities, and even a little bit of noncombat support. This also would be an amazing multiclass with a Rogue, as Sneak Attack and Surprise Attack are different things, and so presumably would stack, to say nothing of combining Charmed Life with Evasion. This is very good.