Illyrian Pirate

A menacing predator stalks the Adriatic Sea. Lying in wait within the coves and natural hiding points of the eastern shore, the Illyrians seek vulnerable prey. Merchants and travelers of any country or creed — none are safe from a surprise boarding. At their peak, the Illyrians dominated the Balkan peninsula as Queen Teuta united Illyria under one banner. Piracy in the Adriatic was made all the more terrifying as it was publicly backed by the Queen herself. This brazen lawlessness was denounced by the Greeks and Romans leading to a bloody war.

Illyrian pirates are known to be as fierce as they are clever. They wield a specialized curved blade — the sica. Its long, curved blade with the edge on the inner curve allows the Illyrians to reach over enemy shields and strike their opponents’ backs and necks. Their lembos, or ramming ships, are crewed by one hundred men, each ready to spill blood and snatch jewels. Once a target is stripped of their goods, they too are sold for whatever profit can be made in the rugged Adriatic markets.

Play Dirty

You have mastered the art of striking an opponent in unexpected places. The curved sica allows you to reach and slice around your target's defenses. Once per turn, when you hit a creature with a sneak attack, you subtract half your proficiency (rounded down) off the target's AC and saving throws until the end of your next turn.

Mariner's 'Mare

You gain advantage on all saving throws and skill and ability checks to control or seize control of a vehicle or mount. This applies on land and sea. If you don't already have proficiency in vehicles (land) and vehicles (sea) you gain it.

Submerged

You gain a swimming speed equal to your walking speed.

While submerged in water you gain advantage to stealth.

Also while submerged in water, you have advantage on attack rolls against creatures submerged in the same body of water as you, that doesn't have a swimming speed.

 

Anchoring

As a Bonus Action, you can make a ranged weapon attack against a creature. On a hit, you can choose to pull yourself towards the creature, pull the creature towards you or reduce it's speed to zero. This attack cannot deal any damage.

If submerged in water, you can do two options of Anchoring.

An Eye For It

Your eyes have sharpened to catch the most minute detail of treasures and the foes that carry them. You gain proficiency and expertise in the Insight and Investigation skills due to your experience with coin and items of value.

You also have advantage on Perception checks to search for items worth at least 1 gp, and you can track them as you would a creature. You can do so by tracking individuals, investigating hearsay, or discerning physical evidence relevant to the item.

King Captain's Quartering

Travelers fear the very mention of your presence as your infamous legend grows. You are now immune to the effects of difficult terrain. You gain a climbing and swim speed equal to your walking speed. When you hit a target with a sneak attack, they make a constitution saving throw (DC 8 + your proficiency bonus + Dexterity modifier). On a failed save, the target loses all resistances and immunities till the end of your next turn.
You can use this feature a number of times equal to your Dexterity modifier (minimum of once), and you regain all expended uses of it when you finish a short or long rest.