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Grace O’Malley Pirate Queen “The Dark Lady of Doona”

Grace O'Malley Pirate Queen "The Dark Lady of Doona"
  • Alias: Gráinne Mhaol, Pirate Queen
  • Gender: Female
  • Race: Irish
  • Occupation: Pirate, Chieftainess
  • Religion: Catholicism (with elements of Gaelic spirituality)
  • Allies: Clan members, fellow seafarers, local leaders supportive of Irish autonomy
  • Enemies: English authorities, rival clans, those who seek to undermine Irish independence
  • Abode/Base of Operations: O’Malley Castle, County Mayo, Western Coast of Ireland
  • Nationality: Irish
  • Languages: Irish Gaelic, English
  • Alignment: Chaotic Good
  • Affiliation(s): O’Malley Clan, Independent Irish Resistance
  • Significant Others: Donal O’Flaherty (first husband), Richard Burke (second husband), family and clan members

In the heart of Ireland, a tempestuous and daring figure emerges from the misty shores of County Mayo – Grace O’Malley, the legendary Pirate Queen. With the wind in her hair and the sea in her veins, Grace defies conventions, taking to the waves as a fearsome sailor, leader, and defender of her homeland.

Character Description: Grace O’Malley is a woman of both wild spirit and calculated strategy. Her raven-black hair dances like the sea spray, mirroring her fierce determination and untamed nature. In the twinkle of her eyes lies the essence of a chieftainess unafraid to embrace the crashing storms of life. Her voice, a melody of command and wisdom, carries tales of both daring escapades and quiet moments of reflection.

Driving Fear and Motivation: While Grace fears the crushing weight of oppression, she also dreads the loss of her people’s freedom, a fate she vows to defy at all costs. The conquering English rule that threatens her beloved land and the traditional way of life she holds dear are her constant foes. This fear fuels her actions, propelling her to seize control of her destiny and steer the ship of fate with her own hands.

Unveiling the Why: Grace’s pursuit of maritime glory and territorial dominion is not merely for personal gain. Deep within her heart, she carries a fervent desire to protect her people’s rights, sovereignty, and ancestral traditions. The salt-kissed air, the rhythmic tide, and the sunsets on the horizon – they are all intertwined with her sense of duty. Her actions reflect her unwavering commitment to a legacy of honor and respect, showcasing her undying loyalty to those she leads.

The Grand Ambition: As the salty winds whisper tales of distant lands and uncharted waters, Grace O’Malley’s grand ambition comes to light. She yearns to secure her family’s legacy and ensure her people’s independence. With each ship she commandeers, each battle she wages, she sails towards a future where her people can thrive without the shackles of foreign rule. Her ambition is to be remembered as a symbol of freedom, an embodiment of Ireland’s unyielding spirit.

In the annals of history, Grace O’Malley’s legacy shines like a lighthouse, guiding the way for generations to come. Her audacious adventures, steadfast resolve, and unquenchable thirst for justice make her a beacon of courage and empowerment, reminding us all that even in the face of adversity, a single individual’s determination can change the course of destiny.

  • D&D 5E Grace O’Malley
  • D&D 5E Grace O’Malley, Pirate Queen
Grace O'Malley

D&D 5E – Mythological Figures: Grace O’Malley | EN World | Dungeons & Dragons | Tabletop Roleplaying Games

Grace O’Malley
Medium humanoid (human), neutral fighter (brutal) 11/rogue (thief) 5
Armor Class 17 (studded leather, defense fighting style)
Hit Points 115 (11d10+5d8+32)
Speed 40 ft.

14 (+2)​18 (+4)​14 (+2)​14 (+2)​12 (+1)​14 (+2)​

Saving Throws Str +7, Con +7
Skills Athletics +7, History +7, Insight +11, Perception +6, Persuasion +12; disguise kit +7, forgery kit +7, navigator’s tools +7, thieves tools +9, vehicle (water) +14
Senses passive Perception 16
Languages English, Gaelic, Latin, Thieves’ Cant
Challenge 10 (5,900 XP)

Background: Nautical. Grace is able to acquire passage on a sailing ship for her and her allies free of charge. She has no control over the ship’s route, departure, or return, and although no coin is required she and her companions do have to help crew the vessel.

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

Brutal Toughness. Grace 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). Grace can take a bonus action to take the Dash, Disengage, Hide or Use Object action, Dexterity (Sleight of Hand) check, or to use thieves’ tools to disarm a trap or open a lock.

Feat: Diplomatic. Grace can make a Charisma (Persuasion) check contested by the Wisdom (Insight) check of a creature that can understand what she says during 1 minute of talking. On a success, as long as Grace remains within 60 feet of it (and for 1 minute afterward) the target is charmed by her. Grace automatically fails on the check if she or her companions are fighting the target.

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

Indomitable (1/Long Rest). Grace can reroll a saving throw that she fails but must use the new roll.

Second-Story Work. Climbing does not cost Grace extra movement. When she makes a running jump, the distance she covers increases by 4 feet.

Second Wind (1/Short Rest). On her turn, Grace can use a bonus action to regain 1d10+11 hit points.

Sneak Attack (1/Turn). Grace deals an extra 10 (3d6) damage when she 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 Grace that isn’t incapacitated and Grace doesn’t have disadvantage on the attack roll.

Extra Attack. Grace attacks three times when she takes the Attack action. When she uses a bonus action to engage in two-weapon fighting using a dagger, she can add her Dexterity modifier to the damage of her fourth attack.

Cutlass. Melee Weapon Attack: +9 to hit, reach 5 ft., one target. Hit: 11 (1d6+1d6+4) slashing damage.

Dagger (4). Melee or Ranged Weapon Attack: +9 to hit, reach 5 ft. or thrown 20/60 ft., one target. Hit: 10 (1d4+1d6+4) piercing damage.

Pistol (2). Ranged Weapon Attack: +9 to hit, range 30/90 ft., one target. Hit: 13 (1d10+1d6+4) piercing damage.

Musket. Ranged Weapon Attack: +9 to hit, range 40/120 ft., one target. Hit: 14 (1d12+1d6+4) piercing damage.

Uncanny Dodge. When an attacker Grace can see hits her with an attack, she can use her reaction to halve the attack’s damage against her.

Grace O'Malley, Pirate Queen

Medium humanoid (human), Chaotic Good

Armor Class: 16 (studded leather armor) Hit Points: 110 (13d8 + 52) Speed: 30 ft.

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

Saving Throws: DEX +8, CON +8, WIS +7 Skills: Athletics +5, Perception +7, Persuasion +6, Survival +7 Senses: Passive Perception 17 Languages: Common, Gaelic


Cutlass. Melee Weapon Attack: +8 to hit, reach 5 ft., one target. Hit: 8 (1d6 + 4) slashing damage.

Flintlock Pistol. Ranged Weapon Attack: +8 to hit, range 30/90 ft., one target. Hit: 10 (1d10 + 4) piercing damage.

Commanding Shout. Grace can use a bonus action to shout an inspiring command to her crew. Allies within 30 feet gain advantage on their next attack roll or saving throw before the start of her next turn.


Evasion.When Grace is subjected to an effect that allows her to make a Dexterity saving throw to take only half damage, she instead takes no damage on a success and half damage on a failure.
Uncanny Dodge.When an attacker Grace can see hits her with an attack, she can use her reaction to halve the attack’s damage against her.
Nautical Expertise.Grace has advantage on all checks related to navigation, ship handling, and seamanship.
Commanding Presence.Grace and her allies within 30 feet have advantage on saving throws against being frightened.
Lucky Charm.Once per long rest, Grace can reroll an attack roll, saving throw, or ability check.
Pirate’s Cunning.Grace can take the Hide action as a bonus action on her turn. She has advantage on Dexterity (Stealth) checks made to hide.


  • Studded Leather Armor
  • Cutlass (finesse, light, 1d6 slashing)
  • Flintlock Pistol (ammunition, range 30/90 ft., loading, 1d10 piercing)
  • Pirate Hat (worn for style and command)
  • Compass and Nautical Charts
  • Personal Trinket (a locket containing a picture of her family)

Magic Items

  • Tricorn of the Sea: A magical tricorn hat that allows Grace to cast Water Walk once per day without expending a spell slot.
  • Captain’s Compass: A compass that provides advantage on navigation-related checks.

Legendary Actions

Grace 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. Grace regains spent legendary actions at the start of her turn.

  • Parry. Grace can expend one legendary action to gain a +4 bonus to AC against one melee attack.
  • Quick Shot. Grace can expend one legendary action to make a single Flintlock Pistol attack.
  • Inspiring Speech. Grace can expend one legendary action to issue a rallying cry, allowing an ally within 30 feet to reroll a saving throw.

Lair Actions

Grace can take lair actions on initiative count 20 (losing initiative ties), causing one of the following effects:

  • Crashing Waves: A wave crashes against the enemies, forcing them to make a DC 15 Strength saving throw or be knocked prone.
  • Fog Veil: Grace can shroud the battlefield in dense fog, granting advantage on Dexterity (Stealth) checks for herself and her allies.
  • Tides of Bravery: Grace’s leadership bolster her crew. Allies within 30 feet gain temporary hit points equal to her Charisma modifier (3).

Currently in the World

Grace O’Malley stands at the helm of her weathered ship, her raven-black hair tousled by the salty sea breeze. Her eyes, as deep and mysterious as the ocean itself, scan the horizon with a mix of determination and anticipation. The sun’s golden rays dance upon her weathered skin, a testament to a life spent under the sun and the stars.

Her attire tells the story of a fearless leader and a seasoned mariner. Draped in a flowing coat of deep green, adorned with hints of gold, she exudes an air of authority that demands respect. A sturdy leather belt cinches her waist, holding a cutlass and a finely crafted pistol – tools of her trade that have seen both fierce battles and triumphant victories.

The ship beneath her feet creaks and sways with the rhythm of the waves, a constant companion in her lifelong journey across the seas. The crew members move about with purpose, their synchronized movements reflecting the harmony she has instilled among them. The deck, polished by years of devoted care, reflects the sparkling expanse of the ocean.

Surrounded by the endless blue of the sea and sky, Grace’s mood is one of quiet contemplation mixed with unwavering resolve. The rolling waves and the vastness of the ocean remind her of the struggles her people face against foreign dominion. Yet, her heart is lifted by the knowledge that she, the Pirate Queen, is a beacon of hope for her clan and all those who cherish Ireland’s independence.

As the ship cuts through the water, Grace O’Malley’s gaze remains fixed on the distant horizon. With the wind in her sails and the spirit of her ancestors at her back, she continues her voyage, steadfast in her mission to protect her homeland and preserve the legacy of the Irish people.

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