(Just addressing this for now.)

As Nate tries to attack the bird lady, he finds that his blade cannot pierce through the wind around her as she moved. He gives chase and tries again at her. She blocks the rapier with her off hand sword and the scimitar again meets with a thud against her feathers.

(Gael and Lilliana are up.)

22 - Wisdom save DC 10
Thank goodness!

As the battle rages around her, Lilliana continues staring down at the deck, refusing to look up; however, she hears the voice urging her. 'On your feet! Fight! Do not lay down to die!' With the urging of the voice, Lilliana forces her breathing to slow and gets to her feet, but maintains a death grip upon the railing as she focuses her attention upon the battle and spends a moment gauging the ebb and flow.

Gaèl is a little startled with the fight breaking out so suddenly, but quickly wins back his composure. He unsheathes the one his shortswords and rushes in to fight off the feathered women.

Shortsword vs AC: 13 DMG: 7 piercing damage

(What the hell is wrong with those rolls dammit.)

OOC: Hey, Vyr? I think Nate is the only character in range of the Aaracokra, on the stern of the ship near the helm. The rest of us are at the bow, on top of the forecastle, with pirates 60ft away and closing.

(Right, i guess i misread that. Thanks for the notice!)

Seeing his new crewmembers take cover, Gaèl follows them to hide from the upcomming pirates, both weapons readied to jump into battle.

Stealth: 8

(Edit: SRSLY WHAT THE HECK)

The pirates move forward closing the distance between  half of the group while widening their distance from Liana.

(30 feet now.)

(Well, no wonder my dagger missed, if they only moved 30ft, they never entered my effective range. Also, just how many pirates are advancing on us?)

Aidan locks eyes with Gael.

"Hold the ladders. It will bottleneck them and might put them on an off footing."

Aidan then moves to the starboard ladder/stairway to block anyone from reaching the forecastle deck.

Movement: As indicated above. Aidan also draws his shortsword.
Action: Hold a shortsword attack until a pirate enters his melee range.
     Attack: 10 Damage: 4 piercing + 2 if sneak attack would apply because of positioning

 Edit: Why dice, why?!?!?

(Ladder yes, Stairway no. But will give you advantage if you stand up there and say 'It's over, I have the high ground, surrender now.')

OOC: While tempting, Aidan is a bit too serious of a character to say that kind of thing aloud without being drunk. Especially if the pirates outnumber us. Do the pirates outnumber us?

(I dont really care about the advantage, that move is just hilarious. I will do roll a twice tho, just in case. I am also not sure if its possible to ready an off-hand attack, if not just ignore that part.)

Gaèl nods in agreement. He unsheathes the second shortsword and then, both weapons readied, slowly walks up towards the staircase. ""Hello there.", he says with a big smile on his face. He then reaches out with his right sword towards the pirates coming from below in a taunting gesture, just like a fencer awaiting his opponent. "It's over! I have the high ground, surrender now!" He then ducks away from the stairs again to try and avoid incoming missiles.

Readied Action in case a pirates makes it upstairs:

Shortsword vs AC: 17 (Adv. if applies: 21) DMG: 9 piercing

Off-hand: 18 (Adv. if applies: 10) DMG: 4 piercing

(For whoever was damaged first - toll the dead is a WIS Saving throw vs DC 15. Damage will be 10 necrotic!)

Liana resists the urge to appear from out of cover. She pinches the air as red bells gong near her target. She whispers, "Hopefully your time is up."

(Gael make a persuasion check with advantage.)

The bird woman moves to strike at the man while also hitting the steering wheel with her other sword.

Attack: 24 Damage: 4

 Her first strike hits the man upon his shoulder, giving a yelp of pain as he staggers away from her. She strikes at the wheel's spokes causing the ship to suddenly start turning towards the city's engines.

Persuasion: 12

Nate tries to hit her again with his rapier, and then he'll also try to turn the wheel further so that it's pointed away from the city. "Get away from the wheel bird brain!"

Rapier 18 Damage 7

(I don't know if I have to roll to hit the wheel since she didn't. All I'm trying to do is turn the wheel even more the way she's trying to go to make it turn in a circle) 

The aaracokra is within 120' of Lilliana, correct?

(Correct, about 90 feet.)

Nate stabs the bird woman at her side and swipes at the ship's wheel, setting the ship's course away from the engine. And as the pirates approach Gael, they look to each other once before shouting, "You underestimate us!", they give a cheer as they continue towards you all.

(Just need Lilliana.)

Attack: 23 Damage: 14

2

Lilliana spots Nate fighting with the aaracokra over the controls of the ship and realizes he needs help desperately! She reaches out with her hand towards the pirate as a strange glow suddenly appears around it just before she sends another burst of the bluish energy streaking across the deck of the ship!

Casting Hex on the captain and then eldritch Blast! Oy! I keep forgetting I don’t have Agonizing Blast yet! So the damage is only 10+2 for a total of 12, not 16. Still not a bad roll!! Also, if that is enough damage to drop the captain, Lilliana will shift her Hex to the closest pirate to her.

(Lilliana, which ability would you like to make the Aaracokra have disadvantage with?)

14

 As the pirates rush up to meet with the half elf proclaiming advantage over them, they find themselves met with Gael's shortsword as Aidan promptly attacks as well from the side. The man is cut down quickly and even more as Gael strikes at another and Liana reveals herself with her [Tooltip Not Found], the pirate giving a cry as he drops dead. The other two pirates strike at the Aidan and Gael as Lilliana curses the bird woman and sending a blast of her eldritch energy her way as well.

Attack: 21 Damage: 5 to Aidan

Attack: 23 Damage: 3 to Gael

I'd like to apply Disadvantage to Strength please.

Aidan takes a nasty slash to the side of his abdomen that bleeds heavily. He grits his teeth as he draws a dagger in his off-hand to make two strikes against his assailant. 

Action: Shortsword Attack, 16 Miss
Bonus Action: Dagger Attack, 8 for 3 + 4 piercing damage