Also, a refresher on the layout of your ship (I'm planning for this fight to take place by means of the aforementioned boarding parties which are busy grappling the ship right now). The two crossbows towards the front of the ship are both actually arcane cannons.
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(I'll go ahead and skip forward since I think you guys have done pretty much everything you need to do, but correct me if I'm wrong and there's anything else that you need to do.)
(Pretty much only thing I can think of on Sae's part is that I realized reading over my post just now she never explicitly told Emrys about the [item]helm of telepathy[ /item] ... I'd think it would be the sort of thing that would occur to her to mention sometime in the ensuing couple of days though, as being perhaps slightly useful strategically in predicting the dragonborn's next move? LOL)
Also, are the two ships flanking us, one on each side? If not, are they on the side with the quarter boat in the second diagram from top, or the side that's clear?)
Drawing one of the arrows she'd prepared with pitch and tow out of her quiver, Sae concentrates on the two approaching ships and begins planning her first shot. Knowing little of this strange gunpowder magic, she yet knew enough to keep her arrows far from any part of the attackers where it was likely they'd store the stuff ... kind of hard to be captured by a pirate ship that's at the bottom of the ocean. But a fire in the rigging that would keep some of the attacking pirates busy quenching it ... that was another matter. And though the closest ship would probably be her target, it would impress 'Hailstorm' even more if she was able to pick out the flagship of this pair of pirates and toast that a little ... She found herself almost on the verge of truly smiling for the first time in a very long while. She hadn't truly allowed herself to know how bitter and lonely her life had been for a long time now, or how long it had been since she'd been able to tuly
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Famh Thrawn Fiadhaich - 'half elven' sorcerer (wild magic) 2, Sleeping Gods - A Dragon Warriors campaign in the Lands of Legend
Quspira Inirali - tiefling cleric (Life domain) 4, Painted's "He'll be the father of my child"
---RETIRED HEROES' REST HOME---
Sae Ivui Nailo - wood elf rogue (inquisitive) 5 , Sea of Death: Captain Hailstorm's Lost Treasure
Ryshraxea "Shra" Naranthi - tabaxi artificer 1, Nyx's Tomb of Annihilation - Group 1
Drawing one of the arrows she'd prepared with pitch and tow out of her quiver, Sae concentrates on the two approaching ships and begins planning her first shot. Knowing little of this strange gunpowder magic, she yet knew enough to keep her arrows far from any part of the attackers where it was likely they'd store the stuff ... kind of hard to be captured by a pirate ship that's at the bottom of the ocean. But a fire in the rigging that would keep some of the attacking pirates busy quenching it ... that was another matter. And though the closest ship would probably be her target, it would impress 'Hailstorm' even more if she was able to pick out the flagship of this pair of pirates and toast that a little ... She found herself almost on the verge of truly smiling for the first time in a very long while. She hadn't truly allowed herself to know how bitter and lonely her life had been for a long time now, or how long it had been since she'd been able to truly give herself to the joy of battle with comrades at her side.
Investigation 5
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Famh Thrawn Fiadhaich - 'half elven' sorcerer (wild magic) 2, Sleeping Gods - A Dragon Warriors campaign in the Lands of Legend
Quspira Inirali - tiefling cleric (Life domain) 4, Painted's "He'll be the father of my child"
---RETIRED HEROES' REST HOME---
Sae Ivui Nailo - wood elf rogue (inquisitive) 5 , Sea of Death: Captain Hailstorm's Lost Treasure
Ryshraxea "Shra" Naranthi - tabaxi artificer 1, Nyx's Tomb of Annihilation - Group 1
Drawing one of the arrows she'd prepared with pitch and tow out of her quiver, Sae concentrates on the two approaching ships and begins planning her first shot. Knowing little of this strange gunpowder magic, she yet knew enough to keep her arrows far from any part of the attackers where it was likely they'd store the stuff ... kind of hard to be captured by a pirate ship that's at the bottom of the ocean. But a fire in the rigging that would keep some of the attacking pirates busy quenching it ... that was another matter. And though the closest ship would probably be her target, it would impress 'Hailstorm' even more if she was able to pick out the flagship of this pair of pirates and toast that a little ... She found herself almost on the verge of truly smiling for the first time in a very long while. She hadn't truly allowed herself to know how bitter and lonely her life had been for a long time now, or how long it had been since she'd been able to truly give herself to the joy of battle with comrades at her side.
Investigation 22
So, the ships are indeed flanking you guys and pirates are trying to board from both sides.
The portside ship is a bit bigger and appears to have a larger crew, so you can conclude that it is likely the flagship of the pair.
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This post has potentially manipulated dice roll results.
Looks like NPCs go first...
Pirate 2 takes two swings with his scimitar at at Areleo Attack 1: 13 Damage: 5 Attack 2: 6 Damage: 8
Yevelda is next, and she uses a bonus action to RAGE; she is not going to frenzy right now to avoid the exhaustion as she might need to perform at her peak again later. She proceeds to attack Pirate 5 twice with her greataxe Attack 1: Attack: 17 Damage: 10 Attack 2: Attack: 19 Damage: 14
Next is William, who strikes at Pirate 7 using two daggers Attack: Attack: 25 Damage: Unable to parse dice roll. BA attack: 14 Damage: 4 If either attack hits, he deals 3 bonus Sneak Attack damage
Pirates 4, 5, 3, 1, 6, and 8 next
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Pirate 4 uses multi-attack; he aims one slash at Areleo and one at Sayyida Attack 1 (Areleo): Attack: 11 Damage: 5 Attack 2 (Sayyida): Attack: 16 Damage: 7
Pirate 5 grunts as the half-orc slashes him across the chest, but he recovers quickly and lunges at her, striking twice with his scimitar Attack 1: Attack: 10 Damage: Unable to parse dice roll. Attack 2: Attack: 16 Damage: 8
Pirate 3 makes two scimitar attacks against Areleo Attack 1: Attack: 19 Damage: 8 Attack 2: Attack: 14 Damage: 4
Pirate 1 draws two pistols; he fires one at William and one at 'Naut Attack 1 (Will): Attack: 18 Damage: 15 Attack 2 ('Naut): Attack: 15 Damage: 4
Pirate 6 takes two swings at Will Attack 1: Attack: 5 Damage: 5 Attack 2: Attack: 19 Damage: 3
Pirate 8, seeing his buddy get slashed across the chest, rushes across the deck to engage Yevelda in battle. The half-orc is now being flanked by the two pirates. Attack 1: Attack: 7 Damage: 3 Attack 2: Attack: 11 Damage: 5
Areleo and Sayyida are up!
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(OOC: If we see them closing on us, how do we not get at least one shot with our cannons and missile weapons before they are in range to board? Or for that matter while they're climbing over their rails, crossing the distance between our ships, and then crossing our rails?)
(OOC: If we see them closing on us, how do we not get at least one shot with our cannons and missile weapons before they are in range to board? Or for that matter while they're climbing over their rails, crossing the distance between our ships, and then crossing our rails?)
(OOC: Honestly... a large part of the reason is because it's easier for me to run it this way. That being said, there's thick fog and you basically ran right into them while rounding a cape; my apologies that I didn't have a good map to show the relative positions of the ships for the start of the encounter. You pretty much had a second or two between realizing the pirates were there and the grappling hooks hitting your railings. The fog isn't so dense that you can't see what's on your deck, but you can't see much beyond that, at least not clearly. Basically, one ship was waiting in ambush as you rounded the cape; the second one wasn't obviously a pirate ship because of the fog until they were next to you throwing their hooks)
Sayyida winced as the pirates blade slipped past her shield, " Ok, your on my shit-list."
She pressed the pirate savagely with the fury of a raging tempest.
Action- Vs Pirate 4 - Attack: 16 Damage: 8 if it hits + 10 Divine Smite.
Bonus Action-
Channel Divinity: Fury of the Tides
Once per turn for the duration, when you hit a creature with a weapon attack, you can choose to push the target 10 ft. away from you. If pushed into an obstacle or another creature, the target takes +3 bludgeoning damage. This lasts for 1 minute.
Sayyida Initiative- 14
" Man the Cannons!"
Just for reference:
arcane cannon
You have two cannons on your deck.
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Also, a refresher on the layout of your ship (I'm planning for this fight to take place by means of the aforementioned boarding parties which are busy grappling the ship right now). The two crossbows towards the front of the ship are both actually arcane cannons.

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(Pretty much only thing I can think of on Sae's part is that I realized reading over my post just now she never explicitly told Emrys about the [item]helm of telepathy[ /item] ... I'd think it would be the sort of thing that would occur to her to mention sometime in the ensuing couple of days though, as being perhaps slightly useful strategically in predicting the dragonborn's next move? LOL)
Also, are the two ships flanking us, one on each side? If not, are they on the side with the quarter boat in the second diagram from top, or the side that's clear?)
Famh Thrawn Fiadhaich - 'half elven' sorcerer (wild magic) 2, Sleeping Gods - A Dragon Warriors campaign in the Lands of Legend
Quspira Inirali - tiefling cleric (Life domain) 4, Painted's "He'll be the father of my child"
---RETIRED HEROES' REST HOME---
Sae Ivui Nailo - wood elf rogue (inquisitive) 5 , Sea of Death: Captain Hailstorm's Lost Treasure
Ryshraxea "Shra" Naranthi - tabaxi artificer 1, Nyx's Tomb of Annihilation - Group 1
(Sae's initiative: 9
==============================================
Drawing one of the arrows she'd prepared with pitch and tow out of her quiver, Sae concentrates on the two approaching ships and begins planning her first shot. Knowing little of this strange gunpowder magic, she yet knew enough to keep her arrows far from any part of the attackers where it was likely they'd store the stuff ... kind of hard to be captured by a pirate ship that's at the bottom of the ocean. But a fire in the rigging that would keep some of the attacking pirates busy quenching it ... that was another matter. And though the closest ship would probably be her target, it would impress 'Hailstorm' even more if she was able to pick out the flagship of this pair of pirates and toast that a little ... She found herself almost on the verge of truly smiling for the first time in a very long while. She hadn't truly allowed herself to know how bitter and lonely her life had been for a long time now, or how long it had been since she'd been able to tuly
Famh Thrawn Fiadhaich - 'half elven' sorcerer (wild magic) 2, Sleeping Gods - A Dragon Warriors campaign in the Lands of Legend
Quspira Inirali - tiefling cleric (Life domain) 4, Painted's "He'll be the father of my child"
---RETIRED HEROES' REST HOME---
Sae Ivui Nailo - wood elf rogue (inquisitive) 5 , Sea of Death: Captain Hailstorm's Lost Treasure
Ryshraxea "Shra" Naranthi - tabaxi artificer 1, Nyx's Tomb of Annihilation - Group 1
Investigation 5
Famh Thrawn Fiadhaich - 'half elven' sorcerer (wild magic) 2, Sleeping Gods - A Dragon Warriors campaign in the Lands of Legend
Quspira Inirali - tiefling cleric (Life domain) 4, Painted's "He'll be the father of my child"
---RETIRED HEROES' REST HOME---
Sae Ivui Nailo - wood elf rogue (inquisitive) 5 , Sea of Death: Captain Hailstorm's Lost Treasure
Ryshraxea "Shra" Naranthi - tabaxi artificer 1, Nyx's Tomb of Annihilation - Group 1
So, the ships are indeed flanking you guys and pirates are trying to board from both sides.
The portside ship is a bit bigger and appears to have a larger crew, so you can conclude that it is likely the flagship of the pair.
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As soon as Sae realizes which ship is likely in command, she aims her bow at its sails and calls to the others, "That'll be the boss!"
Famh Thrawn Fiadhaich - 'half elven' sorcerer (wild magic) 2, Sleeping Gods - A Dragon Warriors campaign in the Lands of Legend
Quspira Inirali - tiefling cleric (Life domain) 4, Painted's "He'll be the father of my child"
---RETIRED HEROES' REST HOME---
Sae Ivui Nailo - wood elf rogue (inquisitive) 5 , Sea of Death: Captain Hailstorm's Lost Treasure
Ryshraxea "Shra" Naranthi - tabaxi artificer 1, Nyx's Tomb of Annihilation - Group 1
Maps:


(If anyone would like to start their character at a different location, just let me know)
'Naut Initiative: 18
Pirate 1: 19
Pirate 2: 9
Pirate 3: 10
Pirate 4: 14
Pirate 5: 19
Pirate 6: 12
Pirate 7: 14
Pirate 8: 4
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NPC Initiative:
Yevelda - 16
William - 16
Harold - 9
Xorich - Is in the kitchen, safely out of harm's way
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Initiative:
Pirate 2
-
Yevelda
William
-
Pirate 4
Pirate 5
Pirate 3
Pirate 1
Pirate 6
Pirate 8
-
Areleo
Sayyida
-
Pirate 7
-
Sae
Harold
'Naut
Emrys
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Areleo would be as close to the on coming pirates as he can before they land on the boat.
Noted, I'll move Areleo closer to the four portside pirates
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Updated map. Are there any other changes that anyone would like to make before the battle begins?

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Looks like NPCs go first...
Pirate 2 takes two swings with his scimitar at at Areleo
Attack 1: 13 Damage: 5
Attack 2: 6 Damage: 8
Yevelda is next, and she uses a bonus action to RAGE; she is not going to frenzy right now to avoid the exhaustion as she might need to perform at her peak again later. She proceeds to attack Pirate 5 twice with her greataxe
Attack 1: Attack: 17 Damage: 10
Attack 2: Attack: 19 Damage: 14
Next is William, who strikes at Pirate 7 using two daggers
Attack: Attack: 25 Damage: Unable to parse dice roll.
BA attack: 14 Damage: 4
If either attack hits, he deals 3 bonus Sneak Attack damage
Pirates 4, 5, 3, 1, 6, and 8 next
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Pirate 4 uses multi-attack; he aims one slash at Areleo and one at Sayyida
Attack 1 (Areleo): Attack: 11 Damage: 5
Attack 2 (Sayyida): Attack: 16 Damage: 7
Pirate 5 grunts as the half-orc slashes him across the chest, but he recovers quickly and lunges at her, striking twice with his scimitar
Attack 1: Attack: 10 Damage: Unable to parse dice roll.
Attack 2: Attack: 16 Damage: 8
Pirate 3 makes two scimitar attacks against Areleo
Attack 1: Attack: 19 Damage: 8
Attack 2: Attack: 14 Damage: 4
Pirate 1 draws two pistols; he fires one at William and one at 'Naut
Attack 1 (Will): Attack: 18 Damage: 15
Attack 2 ('Naut): Attack: 15 Damage: 4
Pirate 6 takes two swings at Will
Attack 1: Attack: 5 Damage: 5
Attack 2: Attack: 19 Damage: 3
Pirate 8, seeing his buddy get slashed across the chest, rushes across the deck to engage Yevelda in battle. The half-orc is now being flanked by the two pirates.
Attack 1: Attack: 7 Damage: 3
Attack 2: Attack: 11 Damage: 5
Areleo and Sayyida are up!
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(OOC: If we see them closing on us, how do we not get at least one shot with our cannons and missile weapons before they are in range to board? Or for that matter while they're climbing over their rails, crossing the distance between our ships, and then crossing our rails?)
Famh Thrawn Fiadhaich - 'half elven' sorcerer (wild magic) 2, Sleeping Gods - A Dragon Warriors campaign in the Lands of Legend
Quspira Inirali - tiefling cleric (Life domain) 4, Painted's "He'll be the father of my child"
---RETIRED HEROES' REST HOME---
Sae Ivui Nailo - wood elf rogue (inquisitive) 5 , Sea of Death: Captain Hailstorm's Lost Treasure
Ryshraxea "Shra" Naranthi - tabaxi artificer 1, Nyx's Tomb of Annihilation - Group 1
(OOC: Honestly... a large part of the reason is because it's easier for me to run it this way. That being said, there's thick fog and you basically ran right into them while rounding a cape; my apologies that I didn't have a good map to show the relative positions of the ships for the start of the encounter. You pretty much had a second or two between realizing the pirates were there and the grappling hooks hitting your railings. The fog isn't so dense that you can't see what's on your deck, but you can't see much beyond that, at least not clearly. Basically, one ship was waiting in ambush as you rounded the cape; the second one wasn't obviously a pirate ship because of the fog until they were next to you throwing their hooks)
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(Oh, I understand now ,,, sorry.)
Famh Thrawn Fiadhaich - 'half elven' sorcerer (wild magic) 2, Sleeping Gods - A Dragon Warriors campaign in the Lands of Legend
Quspira Inirali - tiefling cleric (Life domain) 4, Painted's "He'll be the father of my child"
---RETIRED HEROES' REST HOME---
Sae Ivui Nailo - wood elf rogue (inquisitive) 5 , Sea of Death: Captain Hailstorm's Lost Treasure
Ryshraxea "Shra" Naranthi - tabaxi artificer 1, Nyx's Tomb of Annihilation - Group 1
Sayyida winced as the pirates blade slipped past her shield, " Ok, your on my shit-list."
She pressed the pirate savagely with the fury of a raging tempest.
Action- Vs Pirate 4 - Attack: 16 Damage: 8 if it hits + 10 Divine Smite.
Bonus Action-
Once per turn for the duration, when you hit a creature with a weapon attack, you can choose to push the target 10 ft. away from you. If pushed into an obstacle or another creature, the target takes +3 bludgeoning damage. This lasts for 1 minute.