Free Swashbuckler

A Swashbuckler is a flashy, showy, bombastic adventuring type, usually but not necessarily a swordsman. In Dungeons and Dragons 5e, the Swashbuckler is a Roguish Archetype specializing in a mix of Charismatic Panache and being an expert duelist. Some hear the name Swashbuckler and think pirate, and while that is a perfectly reasonable direction to take, there are plenty of other ways to play one. For every Captain Jack Sparrow among their ranks you’ll also find a d’Artagnan, Peter Pan, Robin Hood, and Zorro.

What sets Swashbucklers apart from other Rogues right away is their Rakish Audacity, allowing one to reliably apply Sneak Attack damage while in one-on-one combat. Additionally, Fancy Footwork grants the Swashbuckler what amounts to a free disengage vs their dueling opponent, for the most daring of acrobatic movements about the battlefield to leave a foe in shambles and disarray.

Speaking of acrobatic maneuvers, more accomplished Swashbucklers can give themselves Advantage on Athletics and Acrobatics checks in order to pull off such marvelous stunts. Never discount the usefulness of a well-timed shove or a daring leap to get yourself out of a jam. With such graceful mobility, your opponents won’t stand a chance against such a Master Duelist, turning a miss into a feint and exploiting the opening.

In the example build provided below, we’ll explore a fun way to build a Swashbuckler into a tough melee combatant that can hold its own with the best of them. Not a tank by any means, but not made of paper, the Thundering Thrillseeker shows off in combat as a nimble duelist that darts in and out of the fight with precision attacks.

Fancy Footwork

When you choose this archetype at 3rd level, you learn how to land a strike and then slip away without reprisal. During your turn, if you make a melee attack against a creature, that creature can't make opportunity attacks against you for the rest of your turn.

Rakish Audacity

Starting at 3rd level, your confidence propels you into battle. You can give yourself a bonus to your initiative rolls equal to your Charisma modifier.

You also gain an additional way to use your Sneak Attack; you don't need advantage on the attack roll to use your Sneak Attack against a creature if you are within 5 feet of it, no other creatures are within 5 feet of you, and you don't have disadvantage on the attack roll. All the other rules for Sneak Attack still apply to you.

Panache

At 9th level, your charm becomes extraordinarily beguiling. As an action, you can make a Charisma (Persuasion) 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.

If you succeed on the check and the creature is hostile to you, it has disadvantage on attack rolls against targets other than you and can't make opportunity attacks against targets other than you. This effect lasts for 1 minute, until one of your companions attacks the target or affects it with a spell, or until you and the target are more than 60 feet apart.

If you succeed on the check and the creature isn't hostile to you, it is charmed by you for 1 minute. While charmed, it regards you as a friendly acquaintance. This effect ends immediately if you or your companions do anything harmful to it.

Elegant Maneuver

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

Master Duelist

Beginning at 17th level, your mastery of the blade lets you turn failure into success in combat. If you miss with an attack roll, you can roll it again with advantage. Once you do so, you can't use this feature again until you finish a short or long rest.