'Naut dutifully fulfills their captain's request, walking up behind the near-lifeless body and casting cure wounds, restoring 6 hit points to the downed sailor.

Pirate 2 - Undamaged
-
Yevelda - 6 damage
William - 11 damage (after 'Naut's healing), prone
-
Pirate 4 Pushed into the ocean by Sayyida
Pirate 5 - Head cleaved in half by Yevelda
Pirate 3 - Just got his throat torn out by Areleo
Pirate 1 - 22 damage
Pirate 6 - Undamaged
Pirate 8 - Undamaged
-
Areleo - 10 damage
Sayyida - 5 damage
-
Pirate 7 - Stabbed with a rapier by Harold
-
Sae - 2 damage from Pirate 1
Harold - Undamaged
'Naut - Undamaged
Emrys - Undamaged

End of round 2, 6 more grappling hooks hit the ship from starboard side! It will take a round for the associated pirates to cross the gap, giving you an opportunity if anyone wishes to cut/burn etc. ropes or crossing pirates before they make it onto the ship.

Back to the top of the round!

Pirate 2, seeing that he's more likely than not about to die, is just going all-in to try to hack up Areleo
Attack: 15 Damage: 3
Attack: 13 Damage: 5

Pirate 8 manages to land a blow on Yevelda... but he doesn't get to saver it long as Yevelda unleashes her fury on him! She strikes at him without thinking, her axe already gleaming with his crewmate's blood! The half-orc attacks wildly, not caring about her own safety
Attack: 22 Damage: 8 + 6 bonus damage if she scores a crit
Attack: 23 Damage: 17 + 1 bonus damage if she scores a crit

William, revitalized by 'Naut's magic, springs to his feet and takes a few steps to the left. Dual-wielding daggers, he strikes at Pirate 6
Attack: 10 Damage: 7
Attack: 19 Damage: 5 

Unfortunately, Will does not have the opportunity to deal sneak attack damage as no one else is next to the pirate.

Pirate 1 finishes climbing the stairs and charges at the guy who just hit him with a beam of magic and summoned a tentacle on him... unfortunately, he doesn't know much about warlocks and this may well come back to bite him if he lands a hit.
Attack: 22 Damage: 5
Attack: 21 Damage: 8

Pirate 6, seeing that Will has been healed and gotten back up, tries to un-heal him.
Attack: 12 Damage: 6
Attack: 20 Damage: 3

Pirate 8, assuming he survived Yevelda's assault, sees an opening in her defenses and attempts to capitalize with two swings of his scimitar.
Attack: 12 Damage: 5
Attack: 20 Damage: 8

6 grappling hooks hit your deck starboard side at the end of last round, pirate reinforcements will be on your deck at the beginning of Round 3 unless something is done about 

Areleo and Sayyida are up!

As it turns out, Pirate 1 made a very foolish decision by attacking Emrys. One of the two attacks hits... only a blast of icy shards explode in the pirate's face. Pirate 1 falls backwards, staring up at the sky glassy-eyed, a thin layer of frost covering his body where Emrys' spell struck him.

Map




(The red dots represent grappling hooks that just hit your deck)

Updated combat tracker:

Areleo will move at an unnatural speed, moving his claws through the pirate's flesh. The longer he stays in this beast form the more savage he becomes. 

Claw attack #1: 16 Damage: 6 

Claw attack #2: 16 Damage: 9 

Arleo having things well in...claw....Sayyida moved quickly across the deck and slashed at the nearest grappling rope.

Action- Vs Rope - Attack: 12 Damage: 5 

Sayyida easily severs one of the lines, but there are still 5 more.

I'll go ahead and take Harold and 'Naut's actions right now

Harold, seeing his brother very fall a second time, lets out a battle cry and launches two attacks at Pirate 6, dual-wielding his rapier and dagger
Attack: 7 Damage: 11
Attack: 20 Damage: 4

'Naut decides to follow Sayyida's lead and use his action to dislodge one of the grappling hooks. They attempt a DC 10 Athletics check to dislodge the hook from the ship's railing.
Athletics: 9

Sae and Emrys are up!

Sae, seeing that she is the farthest from any grappling hooks, decides to try another fire arrow to prevent any more from that side for some time to come.  Raising her eyes to the mainsail of the second ship, she kindles the bundle of tow and fires

========================

Longbow attack 24

Piercing to sail 6, plus fire distraction effect

Okay, so the burning sail will distract the starboard-side pirates for 6 rounds while they scramble to put out the blaze.

Meanwhile, Emrys' tentacle hits Pirate 6, doing 8 cold damage. Simultaneously, a stream of pure eldritch power crosses the deck to hit the farthest grappling hook from Emrys (the hook by the bow of the ship; 120ft is a long range...). The hook breaks from the force, sending an unfortunate pirate into the water with a Wilhelm scream and a splash.

Top of the round, 3 pirates manage to clamber onto the deck.

Pirate 9 Init: 14
Pirate 10 Init: 7
Pirate 11 Init: 2

End of round. 4 rounds until pirates start coming over from the portside ship.

Updated combat tracker

Pirate 2 - Undamaged
-
Yevelda - 8 damage
William - 16 damage
-
Pirate 4 Pushed into the ocean by Sayyida
Pirate 5 - Head cleaved in half by Yevelda
Pirate 3 - Just got his throat torn out by Areleo
Pirate 1 - Killed himself by hitting Emrys
Pirate 6 - 17 damage
Pirate 8 - 23 damage
-
Areleo - 10 damage
Sayyida - 5 damage
-
Pirate 7 - Stabbed with a rapier by Harold
Pirate 11 - Undamaged
-
Sae - 2 damage
Harold - Undamaged
-
Pirate 10 - Undamaged
-
'Naut - Undamaged
-
Pirate 9 - Undamaged
-
Emrys - 7 damage (absorbed by AoA, no 'real' damage)

Top of round

Pirate 2 will use multi attack against Areleo

Attack: 12 Damage: 4
Attack: 8 Damage: 4

Meanwhile, Yevelda recklessly attacks Pirate 8; if she kills it him with her first attack, she use her movement to engage with Pirate 11 and strike him with her second attack

Attack: 23 Damage: 9 + 2 bonus damage on a crit
Attack: 22 Damage: 17 + 9 bonus damage on a crit

Will strikes with his twin daggers at Pirate 6
Attack: 9 Damage: 7
Attack: 13 Damage: 6

If either attack hits, he deals 1 bonus damage from Sneak Attack

Yevelda's first attack decapitates Pirate 8; his head rolls gruesomely across the deck. But as she charges towards Pirate 11, her reckless tactics finally fail her and her swing goes wide.

At the same time, Will's two daggers do their work! The first blade carves pirate 6 across the belly, while the second sinks into the man's throat. The pirate topples backwards into the sea.

Areleo and Sayyida are up!

Updated combat tracker:

Areleo dodge the first attack and takes the second attack head on as he closes in for the pirates throat and heart. 

Claw Attack #1: 24 Damage:9

Claw Attack #2:11 Damage: 6

Sayyida was rapidly running out of targets but seeing the pirate fighting the orc woman still stood she sprinted across the deck and tried to run him through.

Action- Vs Pirate 4 - Attack: 10 Damage: 5 if it hits + 7 Divine Smite.

Both of Areleo's attacks hit home, but Pirate 2 is still standing.

Sayyida, meanwhile, hits home, sending Pirate 11 reeling back.

(Dex save to avoid being pushed off the boat entirely... 8)

...and Sayyida has sent another pirate into the sea. Not that he was likely to survive more than a round after that anyway.

Sae is up!

Updated combat tracker:

The pirates movement is reduced by 10 ft if he tries to move

Quote from OisinmacCameron >>

Seeing a wholly unscathed pirate so close to the two brothers, and how badly William is wounded, Sae screens out all other distractions and sights down her arrow shaft straight at Pirate #10's throat.  Taking a deep breath, she pulls the string back to full draw and lets fly ...,

===============

Longbow attack: 18           Damage: 9 piercing

Insightful Fighting: 5     (As a bonus action, you can make an Insight check against a creature you can see that isn’t incapacitated, contested by the target’s Deception check. If you succeed, you can use your Sneak Attack against that target even if you don’t have advantage on the attack roll, but not if you have disadvantage on it for 1 minute or until you use this feature against a different target.)     Extra damage if successful: 

 ...in the event the pirate is more unfocused than that. extra damage would be 7

Pirate 10 Deception

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