Buccaneer

Swashbucklers, brigands, and sea-raiders, buccaneers thrive in the chaos of a crowded brawl. Where other rogues slip through shadows, a buccaneer wades into the press of enemies with fists raised and a grin on their face.

Their greatest weapon is not a blade, but their swagger. A buccaneer’s charm can unnerve rivals, inspire allies, and turn even the fiercest fight into a stage for their bravado. They know how to make every punch count, striking with precision and unleashing a barrage of blows when surrounded. Against frightened foes, their confidence only grows more dangerous, as they read every flinch and exploit every moment of hesitation.

Whether dueling on the rolling deck of a storm-tossed ship, breaking up a tavern melee, or standing shoulder-to-shoulder with their crew in a desperate last stand, buccaneers fight with their wits, their fists, and the roaring spirit of the sea itself.

Pugilist

When you choose this archetype at 3rd level, you’ve trained to fight with your fists as effectively as with blades. Your unarmed strikes count as simple melee weapons for you and have the finesse property. When you hit with an unarmed strike, you deal damage equal to 1d4 + your Strength or Dexterity modifier (your choice). This damage die increases to 1d6 at 9th level and to 1d8 at 17th level. Immediately after you take the Attack action on your turn and make an unarmed strike, you can make one additional unarmed strike as a bonus action.

Swaggering Assault

Starting at 3rd level, your confidence propels you into battle. You can add your Charisma modifier to your initiative rolls.

In addition, you gain a new way to use your Sneak Attack. You don’t need advantage on the attack roll to use your Sneak Attack against a creature if you are within 5 feet of it, at least one other creature is also within 5 feet of you, and you don’t have disadvantage on the attack roll. All other rules for Sneak Attack still apply.

Beguiling Presence

At 9th level, your charm becomes disarmingly dangerous. You can make Deception, Intimidation, or Persuasion checks as a bonus action.

When you make one of these checks contested against a hostile creature, that creature must succeed on a Wisdom saving throw against a DC equal to the result of your check or become frightened of you until the start of your next turn.

Predator’s Edge

Starting at 13th level, you can easily exploit fear in your foes. You have advantage on attack rolls and ability checks you make against creatures that are frightened of you.

Serpent of the Storm

Beginning at 17th level, you can channel the raging spirit of the ocean through your fists. When you take the Attack action on your turn and make an unarmed strike, you can choose for the strike to deal lightning damage, thunder damage, or its normal damage type.

In addition, once per short or long rest when you hit with an unarmed strike, a great spectral sea serpent erupts from your fist. Each creature of your choice within 10 feet of the target takes thunder or lightning damage (your choice) equal to your Sneak Attack damage.