Swashbuckler Rogue Build Guide – A Pirate’s Life For Me – 2024 Update
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For the purposes of this guide, it will be assumed that you would not be multiclassing. While multiclassing can be excellent for many of these, this is for those who want to play the build all the way through in the same class. Guides that use multiclassing will be separate from these.
For spellcasters, you may notice substantial overlap between the spell lists of builds with the same base class. This is due to each guide utilizing a generically good spell list and not considering extenuating factors that will influence how you particularly sculpt your spell list. When creating your own spell list, you should take into account the campaign setting, what spells any other party members are capable of casting, potential overlap (ritual spells tend to overlap so it’s rare you need multiple people capable of casting them), or potential shortcomings in the parties total spell list. While this guide can definitely help point you in the right direction for crafting a spell list, you should use your judgement and preferences to figure out what spells make the most sense for your character.
To that end, please refer to the Spell List and Spell Tier list for any substitutions you’d want to make to the build.
Why Swashbuckler Rogue?
While the flavor for a Swashbuckler is awesome as who doesn’t want to be a pirate, the subclass is a bit disappointing. You are at odds with your subclass incentivizing close combat, but your smaller health pool and lower AC incentivizing you to stay far away to avoid hits. If you have a martial ally or two who doesn’t mind being up close with you, they can take the hits for you as you dip in and out of combat hitting enemies with Sneak Attacks.
Swashbuckler Rogue
Fancy Footwork (Level 3) – B+ Tier – This is a really nice ability as Rogues seldom want to be right next to enemies when they end their turn.
Rakish Audacity (Level 3) – A- Tier – Bonuses to your initiative and a new and easy way to trigger Sneak Attack is really strong as this means you don’t have to constantly use your cunning action to hide if you need damage.
Panache (Level 9) – C+ Tier – This is an interesting ability as it has both in and out of combat applications, but it isn’t easy justifying using this in combat versus just attacking the enemy. That said, if you want to really hurt an enemies damage potential and you can stay out of their way, you could go for this check and just keep a solid distance so they can’t get to you.
Elegant Maneuver (Level 13) – D Tier – Useful out of combat, I can’t imagine when you would use this in combat.
Master Duelist (Level 17) – C Tier – Turning a missed attack into a potential sneak attack is nice, but you don’t get to use this often and abilities similar to this tend to be stronger.
Quick Level Up Guide
| Level | Class Features/Feat | Notes |
| 1 | Expertise, Sneak Attack, Thieves’ Cant, Weapon Mastery | Sneak Attack 1d6 |
| 2 | Cunning Action | None |
| 3 | Swashbuckler Fancy Footwork Rakish Audacity Steady Aim | Sneak Attack to 2d6 |
| 4 | Feat: Skulker (DEX) | None |
| 5 | Cunning Strike, Uncanny Dodge | Sneak Attack to 3d6 |
| 6 | Expertise | None |
| 7 | Evasion, Reliable Talent | Sneak Attack to 4d6 |
| 8 | Feat: Defensive Duelist (DEX) | None |
| 9 | Panache | Sneak Attack to 5d6 |
| 10 | Feat: Mage Slayer (DEX) | None |
| 11 | Improved Cunning Strike | Sneak Attack to 6d6 |
| 12 | Feat: Constitution to 18 | None |
| 13 | Elegant Maneuver | Sneak Attack to 7d6 |
| 14 | Devious Strikes | None |
| 15 | Slippery Mind | Sneak Attack to 8d6 |
| 16 | Feat: Constitution to 20 | None |
| 17 | Master Duelist | Sneak Attack to 9d6 |
| 18 | Elusive | None |
| 19 | Epic Boon: Boon of Combat Prowess | Sneak Attack to 10d6 |
| 20 | Stroke of Luck | None |
Level One Build
Species: Halfling
Attributes:
| POINT BUY | |
| STRENGTH | 8 |
| DEXTERITY | 15 (+2 background) = 17 |
| CONSTITUTION | 15 (+1 background) = 16 |
| INTELLIGENCE | 8 |
| WISDOM | 10 |
| CHARISMA | 14 |
Class: Rogue
Class Features: Expertise, Sneak Attack, Thieves’ Cant, Weapon Mastery
Skill Proficiencies: Acrobatics, Insight, Investigation, and Perception
Background: Criminal (Alert)
Starting Equipment: Scimitar, Dagger, Shortbow and quiver of 20 arrows, Leather Armor, Thieves’ Tools, and 11 gp + 50 gp from background
Species: Halfling
While I’m not a big fan of what Halfling brings to the table, being able to Hide behind a larger party member is really good if you miss with your Vex weapon and don’t have any other form of obscurement in combat. That said, the other abilities are decent as well, even if they won’t be relevant that often.
Attributes
| POINT BUY | |
| STRENGTH | 8 |
| DEXTERITY | 15 (+2 background) = 17 |
| CONSTITUTION | 15 (+1 background) = 16 |
| INTELLIGENCE | 8 |
| WISDOM | 10 |
| CHARISMA | 14 |
Dexterity and Constitution are always going to be the Rogue’s primary stats, and your extra points can go to either pumping Wisdom or Charisma depending if you want better saving throws or better conversation skills.
Proficiencies: Acrobatics, Insight, Perception, and Persuasion
Common proficiencies for Rogue as between these and your background you have all the DEX skills covered as well as other great proficiencies.
Background: Criminal
Good proficiencies, great feat, and it makes a lot of sense with Rogue in general
Starting Equipment – Scimitar, Dagger, Shortbow and quiver of 20 arrows, Leather Armor, Thieves’ Tools, and 11 gp + 50 gp from background
This is very similar to the starting equipment, but the Scimitar is much better than the Shortsword so you have to take the starting gold to get it.
Class – Rogue
Rogues are a very versatile class with a lot of practical applications in and out of combat making them a fan favorite. Starting off, Rogues come with three abilities: Expertise, Sneak Attack, Thieves’ Cant, and Weapon Mastery.
Expertise allows you to take two of your skills and add double your proficiency bonus to them to make them extremely reliable. While the skills you select really depends on what you personally prioritize, it’s hard to go wrong with Perception and Stealth. These are two excellent skills you are going to constantly use so making them as consistent as possible will constantly pay off.
The second ability is the Rogue’s most iconic one – Sneak Attack. Sneak Attack adds extra damage if you can attack an enemy while you have advantage from any means. Normally, this is going to mean you’re hiding, beat the enemies Perception check, and you’ll have advantage on that attack and can Sneak Attack. Every two levels you add an additional d6 to the damage you deal which is pretty solid scaling, although it will generally not keep up compared to other martial classes.
The third ability, which is really just pure flavor, is Thieves’ Cant. This is like its own language that only other rogues or similarly nefarious individuals would know so you can speak in code and such.
The final ability is Weapon Mastery, and you should take the Scimitar and Shortbow mastery considering that’s what you’re going to be using! As a note, make sure your Scimitar is in your main hand to make use of its Weapon Mastery property effectively.
The Build Level 2 Onward
Level 2-5
Level 2
Class Features: Cunning Action
One of the best abilities on Rogue, you can now convert your Bonus Action into a Dash, Disengage, or the Hide action. While the Hide Action is going to be the most common action taken so you can continuously get Sneak Attacks, Dash and Disengage are also excellent actions to take if you really need to get out of wherever situation you’re in.
Level 3
Class: Swashbuckler
Class Features: Fancy Footwork, Rakish Audacity, Steady Aim, Sneak Attack to 2d6
Level 3 brings your subclass, Swashbuckler, and two new features to the table – Fancy Footwork and Rakish Audacity.
Fancy Footwork gives you a piece of the mobile feat by stopping any creature who you attacked to hit you with an opportunity attack. This is good to dip in and out of a creature’s melee range as, while you want to fight up close, you are definitely no tank.
Rakish Audacity is the Swashbuckler’s key feature that lets them get Sneak Attacks simply by having no allies around them and being 5 feet away from the enemy. While having advantage would obviously be beneficial to help connect, being able to get Sneak Attack in this way is very good and will make your Sneak Attacks super consistent.
Finally, you get Steady Aim which lets you give up your bonus action and movement for a turn in order to have advantage on your next attack. If you have no way to gain advantage otherwise, this is a really nice way to get it!
Level 4
Feat: Skulker (DEX)
Class Features: None
Level 4 brings your first feat, and Skulker is perfect for Rogues! Getting some amount of Blindsight is nice, but the real prizes here are the advantage to hide in battle and missing with an attack doesn’t reveal you which gives you another chance to get that Sneak Attack! These are some really nice abilities that you’re going to get a lot of mileage out of.
Level 5
Class Features: Cunning Strike, Uncanny Dodge, Sneak Attack to 3d6
Level 5 brings two new features to the table with Cunning Strike and Uncanny Dodge.
Cunning Strike is an interesting ability that lets you trade in Sneak Attack damage dice for a small, but generally good additional effect. You start with three different options for your Cunning Strike – Poison, Trip, or Withdraw.
Poison can be solid, but Constitution saving throws are generally the easiest to save out of.
Trip is definitely solid if you have other martial allies and especially if they’re behind you in the turn order (which they will likely be).
Withdraw lets you reposition without drawing opportunity attacks so you don’t have to use your Cunning Action to disengage.
Overall, this ability is pretty good as you have versatile options that can all be impactful!
Uncanny Dodge lets you use your reaction to halve the damage of one incoming attack. Unfortunately, this is a pretty bad ability as multiattacks are going to become more common making the ability to halve just one of those attacks pretty forgettable. Furthermore, Defensive Duelist is going to be taking your reaction more often than not, but if you know that you have to take some damage on a turn, then this is here for you.
Level 6-10
Level 6
Class Feature: Expertise
You get two more bouts of Expertise to pass around, and once again, it really depends on whatever skills you find yourself using often. In a generic sense, I like picking up Insight and either Investigation (if no INT people in your party) or Sleight of Hand.
Level 7
Class Features: Evasion, Reliable Talent, Sneak Attack to 4d6
Level 7 brings two neat abilities with Evasion and Reliable Talent.
Evasion is a really solid ability that makes any effects that forces Dexterity based saving throws way worse against you as you naturally mitigate half of their effect and potentially the whole effect if you pass the save.
Reliable Talent is a cool ability that makes all rolls for skills you’re proficient in be a minimum of a 10, which means you have a much higher chance of passing skill checks with skills you are proficient in and you’ll very rarely fail checks involving skills you have Expertise in.
Level 8
Feat: Defensive Duelist (DEX)
Class Features: None
Level 8 brings another feat, and while you could go straight to 20 Dexterity for the highest AC, attack rolls, and initiative, I like taking two feats instead. To that end, and I really like grabbing Defensive Duelist! Rogues rarely get to use their reaction and they tend to have low ACs, so having the means to deflect attacks if you’re drawing any aggro is really nice.
Level 9
Class Features: Panache, Sneak Attack to 5d6
Level 9 brings your next subclass ability with Panache!
Panache is a strange ability that makes you an unparalleled smooth or smack talker. You can use your action and make a contested Persuasion/Insight roll in order to charm the target in one of two ways. If they’re hostile to you, they’ll have disadvantage on attacks not aimed at you for a minute or until an ally decides to hit them. If they’re neutral or friendly to you, they are charmed and regard you as a friendly acquaintance. This ability is definitely not strong enough to use in battle, but outside of battle this is a good way to persuade people to do things for you that a normal Persuasion roll may not have normally succeeded in. Not a bad utility ability, but a bit disappointing for a ninth level feature.
Level 10
Feat: Mage Slayer (DEX)
Class Features: None
You get yet another feat this level, and you can finally get 20 DEX with Mage Slayer. Being able to really mess with casters is nice as a martial character, and getting a functional charge of Legendary Resistance? Incredible! A really strong feat that I have most of my martial characters taking.
Level 11-15
Level 11
Class Features: Improved Cunning Strike, Sneak Attack to 6d6
Level 11 brings an improvement to your Cunning Strike! Now you can use two Cunning Strike features simultaneously, and while you still have to pay the associated costs, this is still a pretty solid ability!
Level 12
Feat: Constitution to 18
Class Features: None
More health and better saving throws is never a bad thing, even if you’re probably not getting hit that often!
Level 13
Class Features: Elegant Maneuver, Sneak Attack to 7d6
Your next subclass feature is Elegant Maneuver!
You can use your Bonus Action to gain advantage on Acrobatics or an Athletics check on your turn. I guess this is helpful when you really need to pass an Acrobatics roll, but this ability is extremely disappointing.
Level 14
Class Features: Devious Strikes
You get your final upgrades to your Cunning Strikes with Devious Strikes!
Like the original Cunning Strikes, you get three more options that have both higher costs and more powerful effects with Daze, Knock Out, and Obscure.
Daze can limit somewhat limit what an enemy does on their turn, but considering not many monsters have uses for their Bonus Action, this probably isn’t that good of a feature.
Knockout takes out most of your Sneak Attack dice, but you have a chance to render an enemy unconscious until it passes the save or takes damage. This ability could have been strong if they were stunned for a full turn cycle, but just one ally being able to take advantage of this makes this pretty bad.
Obscure is easily the best of these options as you can potentially blind an enemy which is a pretty brutal status condition.
Overall, this ability is not particularly great, but they can’t all be winners.
Level 15
Class Features: Slippery Mind, Sneak Attack to 8d6
Gaining proficiency in Wisdom and Charisma saving throws is very strong, even if it comes a bit late in your progression. Wisdom, in particular, is the most common spell saving throw you’ll have to contend with so you’ll have a substantially better chance of passing these saves now.
Level 16-20
Level 16
Feat: Constitution to 20
Class Features: None
Max health and CON saves is always great!
Level 17
Class Features: Master Duelist, Sneak Attack to 9d6
Level 17 brings your subclass capstone ability – Master Duelist!
Master Duelist lets you reroll a missed attack and give you advantage on that roll once per short or long rest. This is definitely nice as missing with your attack can feel so back-breaking, so getting a way to help you out is great. I dislike that you rarely get to use this, but it is a solid ability.
Level 18
Class Features: Elusive
As long as you aren’t unconscious, enemies can’t have attacks at advantage against you anymore. This can be good, but it’s not too often that enemies are going to have advantage on attacks against you anyway, so this likely isn’t going to come up often.
Level 19
Epic Boon: Boon of Combat Prowess
Class Features: Sneak Attack to 10d6
Your Epic Boon choice, as I will pick for every martial character, is the Boon of Combat Prowess. Converting a miss into a hit is functionally getting an Extra Attack, but better, and I will take an additional attack every day of the week.
Level 20
Class Feature: Stroke of Luck
Every short or long rest, you can turn any failed d20 test into a critical success. Obviously this is pretty strong, even if you don’t get to use it often.
