Path of the Sea Dog

Ar har har, looks like ye chose the life of a pirate, matey. The high seas have fine-tuned yer fighting senses, that's fer sure, and yer camaraderie with yer shipmates has given ye a strong sense of teamwork and loyalty. But yer reckless and carefree attitude, and yer… ahem… "uncivilized" way of life can be both a boon in battle and a burden around the high society folks. They might see ye as nothing but a scurvy dog, aye, but as long as they've got some good rum in stock, they be friends of yers, laddie.

Rum & Song

When ye choose this path at 3rd level, ye gain proficiency in Brewer's tools and the performance skill.

If yer in a place that serves alcohol, or have alcohol in yer possession, ye have advantage on all performance checks, and advantage on all persuasion checks against non-hostile creatures who are also drinking alcohol or who enjoy drinking alcohol.

No matter where ye are in the world, ye can expend 5gp for rum-making materials, and add a single bottle of rum to yer possessions.

Sea Shanty

At 3rd level, ye can bolster yer team's morale with a jaunty jig, matey. Ye can't do this if yer currently raging. As a free action at the beginning of yer turns, ye can sing a line about yer current situation or battle, and if yer teammates all respond with another sung line, ye and all yer mates get a +1 bonus to AC until the start of yer next turn. Yer team's response can simply be a repetition of yer own line, or it can be a generic response such as "yo ho ho and a bottle of rum," but they must all do the response in unison like a chorus. Anyone who doesn't join the response doesn't get the bonus to their AC, including any mates who are silenced, unconscious, or otherwise unable to speak. Ye can continue this shanty on each of yer turns, but ye must come up with a new line on each turn. Yer mates, however, can keep repeating all yer lines, or can keep repeating their generic chorus.

Plunder Yer Booty

At 6th level, ye can check the corpse of any humanoid and see they have some coin left on them. Roll a d4 when ye check a corpse, and if ye roll a 4, it means ye found some coin. Roll the d4 again and gain that much gp.

Guard Dog

Beginning at 6th level, if one of yer mates within 5 feet of ye gets hit by a melee attack, ye can use yer reaction to make a melee attack against the scurvy creature who hurt yer mate.

Drunken Rage

Beginning at 10th level, whenever ye activate a rage, ye can choose to down a bottle of rum and go into a Drunken Rage instead.

A Drunken Rage works the same as a regular rage, but with a coupl'a benefits:

• Yer Rage Damage is doubled
• Ye get Critical Hits on a roll of 19 or 20
• Ye can't be frightened or charmed, and can't fall unconscious
• Ye have advantage on all Constitution and Charisma saving throws

As well as a coupl'a flaws:

• Ye can't use reactions
• Ye can't add yer proficiency bonus to yer attack rolls.
• Ye have disadvantage on all Dexterity, Wisdom, and Intelligence saving throws.

Grace In Injury

Starting at 14th level, yer injuries become part of yer charm. The less HP ye have, the bigger the bonus ye get to Charisma, matey.

When ye have:

• 75-99% of yer max HP, ye get +1 to all Charisma checks and saving throws.
• 50-74% of yer max HP, ye get +2.
• 25-49% of yer max HP, ye get +3.
• 1-24% of yer max HP, ye get +5, yar har har.

Molotov Cocktail

At 14th level, ye gain the ability to make Molotov cocktails with yer rum bottles.

To throw a Molotov cocktail, ye must expend one full bottle of rum, and must have one hand free to throw it. Ye can't use a Molotov on the same turn that ye attack with a two-handed weapon. Otherwise, throwing a Molotov counts as a single ranged weapon attack, with a range of 60 feet. Ye have proficiency with these ranged attacks, and can throw Molotovs as either attacks or Bonus Actions.

On a hit, a Molotov deal 1d6 bludgeoning damage and 2d6 fire damage, and at the start of the target's next turn, they must succeed on a Constitution saving throw or take an additional 1d6 fire damage. (Save DC = 8 + your Dexterity modifier + your proficiency bonus)