Privateer Rogue

Privateers are the mercenaries of the high seas. Whether hired by crown, country or citizen they will sell their skills on the sea for profit. This may mean some are feared while others are loved for their deeds. For example, a Privateer of Chult may choose to serve the mysterious yet good-hearted Triceratops Society, perhaps they are hired by a Merchant Prince of Port Nyanzaru, some might serve a foreign power like Amn, while others may choose to do the work of more nefarious people like Ras Nsi.

Seafaring Skills

Your time on the high seas has helped you develop certain skills. You have spent time rigging boats, raising sails, swabbing the deck and fighting ship to ship.

Starting at 3rd level you gain proficiency in Firearms and Vehicles (water).

Suave Defense

Life on the high seas is for the daring and dashing alike. Your time on the high seas has taught you how to smirk or smile your way through a fierce fight and finish with a fancy flourish. 

Starting at 3rd level when you are not wearing armour or a shield your AC is 10 + Dexterity modifier + Charisma modifier

In addition, when an enemy misses you with an attack you may use your Reaction to make an attack against them. You may use this feature a number of times equal to your proficiency bonus before finishing a long rest.

Fame and Infamy

Adventures on the high seas have helped develop your reputation for good or for ill. Starting at 9th level your reputation on the high seas precedes you. As an action you can make a Charisma (Intimidation) check contested by a creature’s Wisdom (Insight) check. The creature must be able to hear you, and the two of you must share a language. An enemy creature that succeeds on this check is immune to it for 1 minute.

If you succeed on the check and the creature is hostile to you, it must use its Reaction to Dash, moving as far away from you as its movement allows. The creature doesn’t move into obviously dangerous ground, such as a fire or a pit.  Creatures that are immune to Frightened are immune to this effect.

If you succeed on the check and the creature isn’t hostile to you, it is Frightened of you for 1 minute. While Frightened in this way, the target may be willing to give you information or perform a small task that causes no harm to it. This effect ends immediately if you or your companions do anything harmful to it.

Menace of the Seas

Starting at 13th level, you can use a bonus action on your turn to gain advantage on the next Charisma (Intimidation) or Charisma (Deception) check you make during the same turn.

Suave Strike

Starting at 17th level your ability to flourish often flusters your foes. When you hit with an attack, you can deal Psychic damage equal to your Charisma modifier.