The Buccaneer

This is the updated version of The Buccaneer 0.5 as there were formatting issues that caused the abilities to not be displayed.

3rd Level - Bonus Proficiencies:

• Your time on the seas has given you proficiency with Waterborne vehicles, as well as advantage on CON checks related to holding your breath. Additionally, you immediately gain proficiency with Acrobatics or Perception, if you are already proficient with these skills, choose 1 additional skill from the Fighter list. You also gain proficiency with single shot flintlock pistols (if your DM allows). 

3rd Level - Unfaltering Footwork:

You gained your sea legs over the course of your life. 

• You do not suffer from Difficult Terrain created by unstable ground. For example, on a rocking galleon or rumbling earth. Additionally, getting up from prone costs 5ft of movement instead of half.

7th Level - Dirty Follow Through:

• You have a series of moves that you've developed throughout your journey. You can use 1 D.F.T per round, and the save DC is 8+CON+ half of your proficiency bonus rounded down.

1. Flash Powder: As a reaction, when targeted by an attack that you can see within 30ft of you, you may throw a pouch of flash powder at the attacker to impose disadvantage on the roll, additionally the target must pass a CON save or take -2 to the roll.
2. Rope Trick: As an action, when unseen by an enemy, who is no larger than 1 size category than yourself, you can spend your action to tie a rope around their legs and in the same movement make a shoving attack. The target must make an opposed athletics check at disadvantage, being knocked prone if it fails. The target must spend an action to free their legs and stand up. The move automatically fails if the target does not have legs.
3. Unsightly Duelling: As a reaction, immediately following a successful melee attack of opportunity you may make a second attack with your off hand weapon (Hand crossbow/single shot flintlock) targeting the site of the initial attack (rules for off hand weapons apply). If you hit the target they take an additional 2d6 piercing damage on top of the weapons damage.
4. Restless Grapple: As an action, when you are grappling a humanoid, or are grappled by a humanoid, you can attempt to headbutt your target (rolled with STR+PROF), dealing 1d4 bludgeoning + STR damage. On a successful attack the target must pass a CON save or suffer 1d6 bleeding damage for 3 rounds (can be ended early with healing). This attack fails to cause a bleed effect against non-living enemies. As a reaction, when you are grappled by a monster larger than you, you may immediately attempt to bite them (rolled with STR+PROF), dealing 2d4 piercing + STR damage. The target must then pass the same CON save.
5. Dishonourable Disarming: To activate this ability you MUST say "Yar'gh". As an attack action, you may take an attack to kick your opponent in the heat of battle (one vs one combat only), on a successful hit this move deals double unarmed damage (1+STRx2). This move does not work on creature's above size Large.

10th Level - Dead Man's Distorted Parley:

• You've gained some mastery of the seas many secrets. You gain the benefit of the Mirror Image spell once per long rest by channelling the mysterious powers of the oceans to create a mirage of yourself. Additionally, you gain proficiency in Deception and Intimidation, if you are already proficient in Intimidation, you instead gain Expertise.

15th Level - Captain's Gamble:

• You've learned to make your own luck on your many adventures. Once per short rest you may guarantee a critical hit after having succeeded in passing the target's armour class twice. To activate this ability you must acknowledge that you hit the target and declare the gamble, once done you roll again attempting to hit the target again and if you do the attack is treated as a critical hit. No matter what you must take the result of the second roll.

18th Level - "Down with the Ship":

• It all culminates in this moment, your tricks combined with the darkest secrets of the sea has left you with one final option, at a point in battle when you deem the situation unwinnable you may scuttle yourself as an action. When you so choose you may declare your intention to 'go down with the ship', at which point you have 1 round before you explode, immediately dealing a number of d6 equal to your Hit Die total of Force or Fire damage. Upon exploding you immediately drop to 0HP and have 2 failed death saves. Any creature within 15ft of you must succeed on a DC 8+CON+PROF Dexterity save to reduce the damage to 3 quarters damage (further reduced to a minimum of 1 quarter damage with abilities such as Evasion, Resistance, Immunity. Regardless of abilities any creature will take 1 quarter damage at least), and on a failed save you take full damage and are pushed 10ft away. 

3rd Level - Additional Speed:

• You gain a Climbing and Swimming speed equal to your Walking speed.