Base Class: Bard
Swashbuckler bards grow up jumping from one boat to another, making fun of their friends and mocking their enemies. They are well known for their ability to improvise and easily get in and out of combat mostly unharmed. They use anything in their surroundings on their favor, this includes (but is not restricted to) chairs, tables, barrels and even their smaller or bigger friends. Their strategy consist into infuriate their enemies to make them fail. Throw things to disengage and use their panache to attack first (when no one expected) and run first.
Level 3: Bonus Proficiencies
When you join the College of Swashbuckling at 3rd level, you gain proficiency with medium armor and the scimitar. If you’re proficient with a simple or martial melee weapon, you can use it as a spellcasting focus for your bard spells.
Level 3: Deck Brawling
Starting at 3rd level, your self-confidence allows you to get in and out of combat safely.
In addition to your Dexterity bonus, you may add your Charisma modifier bonus to your initiative, once per long rest.
On each of your turns in combat, as a bonus action you can choose to take the dodge or disengage action. To succesfully dodge or disengage as a bonus action, you must succeed on either an athletics or acrobatics with a DC 12 skill check. You can use availible objects/terrain that are present to kick, throw or jump over, things such as; chairs, tables, barrels, other objects or even other allies, and use anything small to medium sized at your favor, in your vincinity to put a barrier between you and your enemy.
You automatically gain two handed fighting style.
Two-Weapon Fighting
When you engage in two-weapon fighting, you can add your ability modifier to the damage of the second attack.
Level 3: Mocking Failure
At 3rd level, when a hostile creature you can see fails an attack against you (spell, ranged or melee). You can cast vicious mockery as a reaction targeting them, once per turn.
Level 6: Dirty Tricks
When you reach 4th level, all those years in the sea allowed you to learn how to fight dirty, you can choose 2 tricks and another trick at levels, 8, and 10.
Disarm
You can use sleight of hand as a bonus action with a contested skill check vs your opponent's perception. If you succeed with a higher result or tie thier roll, you may disarm your opponent, this requires a free hand or a finesse weapon.
Distraction
You can use your deception with a contested skill check vs your opponent's insight, as a bonus action. If you succeed with a higher result or tie thier roll, your enemy has disadvantage on the next attack he receives.
Feint
You can use your deception as a bonus action with a contested skill check vs your opponent's insight. If you succeed with a higher result or tie thier roll you may have advantage on your next attack against the deceived creature.
Swap Positions
You can use athletics or acrobatics with a DC 12 skill check, as a bonus action to leap, jump, or maneuver quickly to swap positions with an ally within 10ft
Level 14: Extra Attack
Starting at 14th level, you can attack twice, instead of once, whenever you take the Attack action on your turn.