As the ultimate jack of all trades, a 
Bard can fill just about any role in your party. While the 
Rogue is the archetypal thief, the Bard brings some unique abilities to the table that can make sneaking, stealing, and lockpicking extremely fun and easy. The combination of Disguise Self and easy Persuasion/Deception make it so that you can practically rob NPCs blind right in front of their noses.
In this guide, we’ll go over the best race, spells, feats, and equipment for a thief bard, as well as some tips that will help you steal everything in sight without getting caught.
Summary
This build is all about being an effective thief. To that end, we’ll be focusing on the Bard‘s strengths as a spell caster and skill master, rather than attempting a poor imitation of a Rogue. For this reason we’ll be using the 
College of Lore subclass and not one of the martial subclasses.
Character Creation
The smaller races are ideal for a thief character. Most of them have advantage on Stealth checks, and by shrinking yourself even further with the Enlarge-Reduce spell, you can access places that you wouldn’t otherwise be able to. Halflings get the Lucky feature, which allows them to reroll any 1. This is a huge benefit for a Bard, since rolling a 1 is often the only way you will fail a skill check. For your subrace, choose the Lightfoot Halfling for advantage on Stealth checks through the Naturally Stealthy feature.
For background and skills, it may be tempting to take Sleight of Hand, and you can certainly do that for the early levels if you wish, but keep in mind that we’ll get proficiency in this skill through the College of Lore subclass at level 3. For that reason you may want to avoid it, along with Arcana and Intimidation, which you’ll also get at that level. On the other hand, Stealth is an obvious choice. Perception is also great since there will be times when you’ll want to leave your party and sneak around alone, which means you won’t have the advantage of three extra sets of eyes to spot every trap or mechanism.
Every Bard should also be maximizing their conversational skills – Persuasion, Deception, and Insight. You’ll be using these skills even more as a thief to get yourself out of trouble when you get caught. The Criminal background offers Deception and Stealth proficiency, which are both great for our purposes.
- Race/Subrace – Halfling/Lightfoot Halfling
- Class – Bard
- Abilities
- 8 Strength
- 16 Dexterity
- 13 Constitution
- 10 Intelligence
- 10 Wisdom
- 17 Charisma
- Background – Criminal
- Skill Proficiencies
- Insight
- Perception
- Persuasion
To see what spells you’ll want to pick during Character Creation, see the following section.
Spells/Abilities
Unlike clerics, druids, paladins, and wizards, you can’t change your spells on the fly, so you need to be selective about which ones you learn. We’ll be focusing on spells that will help you avoid detection as well as providing some useful combat support. Like everything in this guide, these are only suggestions – you should consider your party composition and whether you need to compensate for any gaps in your group’s capabilities, such as healing or crowd control.
Cantrips:
- Vicious Mockery
- Your only real option for a damaging cantrip, which also offers a decent debuff to support your melee friends.
- Light
- You won’t have Darkvision as a Halfling. You can’t have this active while you’re sneaking around, but you can use it everywhere else, including in combat. The rest of your party can benefit from it as well. Characters without Darkvision have disadvantage on your attacks in low light, so this spell is actually a solid combat buff (that doesn’t require concentration).
Spells:
- Disguise Self
- You’ll never get caught – because you were never there!
- Charm Person
- Normally not worth taking due to its downside, especially since you will rarely fail skill checks in dialogue anyway. However, combine this with Disguise Self, and just like that, no more downside! Drop your disguise after you use this, and they won’t be able to accuse you of anything.
- Healing Word
- Heal someone at range with just a bonus action. A useful spell to have even if you aren’t the party’s primary healer.
- Sleep
- This is a solid crowd control ability that can give you time to escape or get your party into position. It’s always successful – no saves or attack rolls required. You can even use it on multiple targets. Very powerful at low levels.
Song of Rest:
This class feature gives you the option to take a third Short Rest each day. Short Rests are the best way to heal your party when you’re not in combat. Don’t waste your spell slots when you can Short Rest!
Spells:
- Feather Fall
- At least one person in your party should have this. This spell is marked as a ritual, meaning it does not cost a spell slot if used outside of combat.
Subclass:
You’ll be taking the College of Lore subclass at this level. The other Bard subclasses offer martial combat bonuses that won’t help you much as a thief.
Your subclass will give you Cutting Words, a powerful reaction. You’ll also get proficiency in Arcana, Intimidation, and Sleight of Hand, and you can choose two skills that you are proficient in for Expertise. You are now looking at an incredible +13 bonus to Sleight of Hand and Stealth before any other bonuses are applied.
Expertise:
Spells:
- Knock
- This spell is a waste on most locks, which you can easily open by picking. But there are a few doors in the game that require a key, and this spell will let you walk right through them.
Cantrips:
- Mage Hand
- Useful for levers and traps that you can’t reach. Unfortunately it’s not able to pick locks or pockets for you, which is why we didn’t take it right away.
Spells:
- Invisibility
- Sometimes being sneaky isn’t enough and you need to disappear altogether. This spell is best utilized in turn-based mode since it has a limited duration.
Feat:
The best option here is a straightforward Ability Improvement (+1 Charisma, +1 Constitution) to even out your odd scores and improve your effectiveness in both combat and dialogue.
You’ll gain Font of Inspiration and Improved Bardic Inspiration at this level, making you an Inspiration machine. Be sure to use this buff as much as possible!
Spells:
- Glyph of Warding
- Since you’re sneaking around a lot anyway, you may as well scout ahead and lay some traps of your own. You can also throw this out mid-battle as a regular old area-of-effect.
You’ll get the Countercharm action at this level, which can give your party the upper hand against enemies that charm and fear.
You’ll also gain your first spells through Magical Secrets. You’ll only get a few of these, but they can be spells from any class’s spell list, so choose carefully.
Spells:
- Enhance Ability
- This spell can let you roll twice on any skill check, which is immensely useful in both dialogue and combat.
Magical Secrets:
- Enlarge-Reduce
- Since we chose a smaller race, casting the Reduce version of this spell on yourself will allow you to fit into burrow holes. If you already have this spell on another character, you can take Pass Without Trace instead to help your less Stealth-inclined allies when you can’t go it alone.
- Arcane Lock
- Use it on a door to limit the number of enemies you have to deal with at one time. It can be a huge strategic advantage. It’s also guaranteed to work and lasts for 10 turns without requiring concentration.
Spells:
- Dimension Door
- Immensely helpful for gaining the high ground and correcting any positioning issues in combat. Since you can take someone with you, this spell can let you move half your party into position with a single action.
Spells:
- Greater Invisibility
- Like Invisibility, but greater! Unlike the lesser version, you can do whatever you want without breaking this – including picking pockets! Best used in turn-based mode since it only lasts for 10 turns.
Feats:
We recommend the Ritual Caster feat for two extra spells that don’t require spell slots when cast out of combat, namely:
- Find Familiar
- The cat familiar is especially useful for our purposes – its meow causes all nearby NPCs to go investigate. Unlike Minor Illusion, the familiar persists and can keep causing distractions without you having to cast it again.
- Longstrider
- Gain an extra 3m to your movement speed for the rest of the day, without even using concentration. Not bad.
Spells:
- Hold Monster
- Put this on a boss and watch your melee go ham.
You’ll gain Improved Bardic Inspiration and Expertise at this level. Expertise in Persuasion, Deception, or Intimidation will make you unstoppable in dialogue checks.
Skills:
- Persuasion (or Intimidation)
- Deception
Cantrips:
- Minor Illusion
- Great for creating distractions, and as a cantrip it’s free to cast.
Spells:
- Bane
- A very effective multi-target debuff. Feel free to take a different spell at this point if you feel your party is missing something important.
Magical Secrets:
- Counterspell
- Someone in your party should have this. You can choose to Nope someone’s spell as a reaction. If your party already has it covered, you can opt for Haste instead.
- Gaseous Form
- Get your whole party through burrow holes and the like. At this level, a level 3 spell slot is no big deal. You could opt to replace Feather Fall once you take this spell.
Spells:
- Eyebite
- One of two options for a level 6 spell, the other being Otto’s Irresistible Dance. Eyebite has broader applications since you can choose how to use it, and it lasts for a lot longer (if your concentration isn’t broken).
Spells:
- Greater Restoration
- Remove just about any negative status effect. If someone in your party already has this, you can opt for something else that you’re missing.
Feats:
We recommend another Ability Improvement for two additional points in Dexterity. But you can always opt for something more flavorful if it strikes your fancy.
Equipment
We’ll focus on items that improve your stealth. For your weapons, pick up the best rapier and hand crossbow you can find.
Act 1
- Leather Armour +1
- This armor should be easy to find as loot or from many merchants, including Roah Moonglow, the Zhent trader in the Goblin Camp. It gives +1 to Stealth checks.
- Spidersilk Armour
- Worn by Minthara. It gives +1 to Stealth checks and advantage on Constitution saving throws.
- Amulet of Misty Step
- Found in a chest in the Defiled Temple. Lets you use the Misty Step spell, correcting problematic positioning with a mere bonus action.
- Shapeshifter’s Boon
- Dropped by the Strange Ox if you kill it. Gives +1d4 to all skill checks when you’re disguised.
Strategy & Tactics
Whenever you’re up to your thieving shenanigans, you should always use Disguise Self. This will let you take advantage of the Shapeshifter’s Boon bonus, as well as preventing people from pointing fingers at you if you’re caught.
Your companions will not be as stealthy as you, so you’ll generally want to do your thieving solo. Toggle off Group Mode (G on the keyboard, left trigger on a controller) to de-couple their movement from yours and go it alone. They can also help you by drawing NPCs’ attention elsewhere.
Spells like Invisibility are best utilized in turn-based mode, since they last for a limited number of turns. Turn-based mode will allow you to take your time and plan your moves carefully.
Thank you for this guide, it’s exactly what I was looking for and provides great detail. I wanted to replace Astarion in my party and as a bard I wasn’t doing much dps anyway. So, thieving is a good replacement. However, I’m having trouble with the Disguise Self mechanics. I’m using the dialogue mechanic to split out of the party, disguising myself, successfully executing the pickpocket, ending the dialogue then popping out of disguise. Actually I’ve tried several variations on when to come out of disguise. The merchant always identifies me. My only option is to move a fair distance away before ending the dialogue. But I can do that whether I am in disguise or not.
Can you provide a little more information on how I should be using disguise?