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Captain Charles Vane: The Dread Pirate of the Caribbean

Captain Charles Vane: The Dread Pirate of the Caribbean
  • Alias: Captain Vane
  • Gender: Male
  • Race: Human
  • Occupation: Pirate Captain
  • Religion: Irreligious
  • Allies: Edward Teach (Blackbeard), Calico Jack, Anne Bonny, Mary Read
  • Enemies: British Royal Navy, Spanish Armada, merchant ships, rival pirates
  • Abode/Base of Operations: Nassau, New Providence Island (pirate stronghold)
  • Nationality: English
  • Languages: English, some Spanish and French
  • Alignment: Chaotic Evil
  • Affiliation(s): Independent pirate captain
  • Significant Others: None officially recorded

Charles Vane, a notorious pirate, a man driven by a relentless thirst for freedom and adventure. As a character, he embodies the very essence of the lawless era of piracy in the Caribbean.

Introduction: In the dangerous waters of the Caribbean, Charles Vane is a name that strikes fear into the hearts of sailors and merchants alike. He is a man of indomitable spirit and an unshakable belief in his own freedom, making him an enigmatic and formidable figure in the Golden Age of Piracy.

Character Description: Vane is a rugged, weather-beaten man with a wild beard and piercing eyes that seem to constantly search for his next conquest. He dresses in tattered clothing adorned with stolen riches, a stark reflection of his disdain for authority and convention. He is fearless, ruthless, and utterly unapologetic about his life choices.

Fears: Charles Vane fears one thing above all else: captivity. He abhors the idea of being imprisoned, restricted, or controlled in any way. This fear fuels his determination to live a life outside the boundaries of society’s rules. He would rather face the perils of the open sea than be confined within the walls of a cell.

Motivation: His driving force is the pursuit of absolute freedom. He seeks to live life on his own terms, answering to no one but himself. The thrill of the chase, the taste of stolen riches, and the wind in his hair are the treasures he values most. Vane yearns for the uncharted horizons of the ocean, where he can defy empires and rewrite his own destiny.

Ambitions: Charles Vane aspires to become a legend, a name whispered in awe and terror across the Caribbean. He seeks not only wealth but also a legacy that will outlive him. His goal is to create a pirate utopia, a place where the free-spirited and rebellious can thrive beyond the reach of oppressive governments.

In the tumultuous world of piracy, Charles Vane stands as a symbol of defiance, a man who sails against the tide of convention, seeking the ultimate prize: his own unbridled freedom.

  • Captain Charles Vane 5e
  • Charles Vane 5e
Early 18th century engraving of Charles Vane, Captain Charles Vane
Early 18th century engraving of Charles Vane

Medium humanoid (human), neutral evil

Armor Class 15 (leather armor) Hit Points 110 (13d8 + 52) Speed 30 ft.

16 (+3)18 (+4)18 (+4)14 (+2)12 (+1)16 (+3)

Skills Acrobatics +7, Athletics +5, Intimidation +6, Perception +4, Stealth +7 Senses passive Perception 14 Languages Common, Pirate Cant Challenge 9 (5,000 XP)

Special Equipment. Captain Charles Vane carries a cutlass, a flintlock pistol, a bandolier of pistol shot, and a tricorn hat.

Cunning Action. On each of his turns, Captain Charles Vane can use a bonus action to take the Dash, Disengage, or Hide action.

Evasion. If Captain Charles Vane is subjected to an effect that allows him to make a Dexterity saving throw to take only half damage, he instead takes no damage on a success and half damage on a failure.

Nimble Escape. Captain Charles Vane can take the Disengage or Hide action as a bonus action on each of his turns.

Pirate’s Resilience. Captain Charles Vane has advantage on saving throws against being frightened.


Multiattack. Captain Charles Vane makes two cutlass attacks.

Cutlass. Melee Weapon Attack: +7 to hit, reach 5 ft., one target. Hit: 8 (1d8 + 4) slashing damage.

Flintlock Pistol. Ranged Weapon Attack: +7 to hit, range 30/90 ft., one target. Hit: 11 (1d10 + 4) piercing damage. Captain Charles Vane must spend a bonus action to reload the pistol.

Parry. When another creature damages Captain Charles Vane with a melee attack, he can use his reaction and expend one superiority die to reduce the damage by the number he rolls on his superiority die + 3.

Uncanny Dodge. When an attacker he can see hits him with an attack, Captain Charles Vane can use his reaction to halve the attack’s damage against him.


Counterattack. When a creature misses Captain Charles Vane with a melee attack, he can use his reaction to make a cutlass attack against the attacker.

Lair Actions

Fury of the Storm. Once per day, Captain Charles Vane can summon a fearsome storm in his vicinity. This storm lasts for 1 minute, and during this time, the area becomes heavily obscured. Vane gains resistance to all damage while in the storm. Creatures within the storm must make a DC 15 Strength saving throw or be pushed 15 feet away from him. After the storm ends, Captain Charles Vane cannot use this ability again until he has completed a long rest.

Legendary Actions

Captain Charles Vane can take 3 legendary actions, choosing from the options below. Only one legendary action option can be used at a time, and only at the end of another creature’s turn. He regains spent legendary actions at the start of his turn.

Move. Captain Charles Vane moves up to his speed without provoking opportunity attacks.

Attack. Captain Charles Vane makes a cutlass or flintlock pistol attack.

Evasive Maneuver (Costs 2 Actions). Captain Charles Vane uses his Cunning Action or Nimble Escape.

Swashbuckler’s Gambit (Costs 3 Actions). Captain Charles Vane takes an additional action on his turn.

Description Captain Charles Vane is a cunning and ruthless pirate captain known for his quick reflexes, deadly marksmanship, and fearlessness in battle. He wears leather armor adorned with various trinkets and carries a menacing cutlass and a flintlock pistol at his side. His tricorn hat casts a shadow over his cold, calculating eyes. Vane often lurks in the treacherous waters of the Caribbean, ambushing merchant ships and terrorizing coastal settlements. He fears nothing and will stop at nothing to amass wealth and power, even if it means resorting to betrayal and brutality. Vane’s ultimate goal is to become the most feared and legendary pirate captain in history.

D&D 5E Mythological Figures: Charles Vane

Charles Vane

For more than half a decade before that he earned a fearsome reputation as a ruthless and cruel pirate, quickly taking command of small fleets and becoming one of the Republic of Pirates’ leaders in Nassau.

D&D 5E – Mythological Figures: Charles Vane | EN World | Dungeons & Dragons | Tabletop Roleplaying Games

A terror on the waves of the Caribbean, the buccaneer Charles Vane is thought to have been 41 when they finally put him to the noose in Port Royal, Jamaica on March 29th in 1721.

After his first capture in 1718 he accepted the King’s Pardon but it was a brief reprieve and within months his criminal doings on the high seas continued. Rejoining with Calico Jack Rackham and others, he took at least a dozen ships before a shipwreck left him without a crew on an uncharted island in 1719. Ultimately a ship loyal to the British crown stopped there to pick up freshwater, an acquaintance recognized Charles for who he was, and he was taken to Port Royal to begin the process of his trial and execution.

Charles Vane​

Medium humanoid (human), chaotic evil rogue (mastermind) 5/fighter (brute) 7
Armor Class 17 (studded leather, sealegs)
Hit Points 85 (5d8+7d10+24)
Speed 40 ft., climb 40 ft., swim 40 ft.

14 (+2)​18 (+4)​14 (+2)​14 (+2)​10 (+0)​14 (+2)​

Saving Throws Dex +8, Int +6
Skills Athletics +6, Deception +10, Insight +4, Intimidation +10, Perception +4, Stealth +12; navigator’s tools +6, thieves’ tools +8, vehicles (water) +12
Senses passive Perception 14
Languages English
Challenge 8 (3,900 XP)

Background: Sailor (Pirate). Vane can make minor transgressions against the law—stealing meals and drink, shoplifting, destroying inexpensive property, and the like—without anyone reporting him to the local guard.

Action Surge (1/Short Rest). Once on his turn, Vane can take an additional action on top of his regular action and a possible bonus action.

Brutal Toughness. Vane gains a +1d6 bonus to saving throws and death saves (treating final results of 20 or higher on a death saving throw as a natural 20).

Cunning Action (1/Turn). Vane can use a bonus action to take the Dash, Disengage, Help, or Hide action.

Fast Learner. After Vane has heard a creature speak for 1 minute or longer, he can mimic its manner of speaking as long as he knows the same language as the creature (allowing him to seem like he is local to a given region).

Feat: Mobility. Vane can Dash through difficult terrain without requiring additional movement. Whenever he makes an attack against a creature, he doesn’t provoke opportunity attacks from that creature until the end of his turn.

Fighting Style: Sealegs. As long as he is not wearing heavy armor or using a shield, Vane gains a +1 bonus to AC, and he gains both climbing and swimming speeds equal to his speed (included above).

Second Wind (1/Short Rest). On his turn, Vane can use a bonus action to regain 1d10+7 hit points.

Sneak Attack (1/Turn). Vane deals an extra 10 (3d6) damage when he hits a target with a weapon attack and has advantage on the attack roll, or when the target is within 5 feet of an ally of Vane that isn’t incapacitated and Vane doesn’t have disadvantage on the attack roll.

Tactician. Vane is able to use the Help action to aid an ally attacking a creature as long as the target of the attack is able to see and hear Vane and is within 30 feet of him.

Extra Attack. Vane attacks twice when he takes the Attack action.

  • Cutlass. Melee Weapon Attack: +8 to hit, reach 5 ft., one target. Hit: 11 (2d6+4) slashing damage.
  • Dagger (4). Melee or Ranged Weapon Attack: +8 to hit, reach 5 ft. or thrown 20/60 ft., one target. Hit: 10 (1d4+1d6+4) piercing damage.
  • Pistol (4). Ranged Weapon Attack: +8 to hit, range 30/90 ft., one target. Hit: 8 (1d10+3) piercing damage.
  • Musket. Ranged Weapon Attack: +8 to hit, range 40/120 ft., one target. Hit: 9 (1d12+3) piercing damage.

Uncanny Dodge. When an attacker Vane can see hits him with an attack, Vane can use his reaction to halve the attack’s damage against him.

Currently in the World

Charles Vane is a rugged and imposing figure, standing at an above-average height with a muscular and well-built frame. His sun-kissed skin bears the weathered marks of a life spent at sea, tanned from the relentless sun and adorned with various scars that tell tales of past battles and skirmishes. His dark, unruly hair falls to his shoulders, framing a weathered face with a strong jawline and piercing blue eyes that seem to hide a world of secrets and cunning.

Currently, Charles Vane finds himself on the deck of his notorious pirate ship, the “Raging Tempest.” The ship is a formidable vessel, with tattered black sails billowing in the wind and a hull adorned with the skull and crossbones, the infamous Jolly Roger flag. The deck is bustling with a motley crew of cutthroat pirates, each going about their duties under Vane’s watchful gaze. The salty sea breeze whips through his hair as he stands at the helm, surveying the open ocean.

Vane’s mood is a volatile mixture of intensity and ruthlessness. His eyes narrow with a predatory glint as he scans the horizon, always on the lookout for potential targets or rivals. There’s an air of menace about him, a palpable sense that danger lurks beneath his every action. He’s a man driven by a relentless desire for power and wealth, and his current surroundings and mood reflect the harsh and unforgiving life of a pirate captain in pursuit of his goals.

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