(Frightened for 5 minutes, you have to avoid looking over the railing of the ship or else you'll suffer disadvantages. And cannot move with 5 feet of the edge of the ship while Frightened. You can take a turn trying to calm your nerves by doing a wisdom save, DC of 10.)

As the scream sounds out from Lilliana, the pirates look over to the group of Aiden, Lilliana, and Gaèl. The Aarakocra yells out for the others to get them and that she'll handle the man. They have not noticed Nate, who managed to get behind them amazingly, and Liana, as she is crouched by the ship's inner railings.

@Nate

OOC: Since the pirates are at the Stern and we (except Nate) are at the bow, I assume we have a few seconds to ready ourselves? Also, from your description of a railing, does that mean we are on top of a forecastle of sorts? With stairs/ladders that the pirates will have to climb to get to us?

Aidan quickly rushes Lilliana to the center of the ship, next to the "inner railing", and attempt to reassure her while taking cover from any ranged attacks the pirates might fire. (Effectively using the "Help Action" for her WIS Save if possible.)

 Before she attacks Nate will attack her with his swords after her crew rush his companions.

Rapier 14 Damage 4

Scimitar 8 Damage 9

If with advantage, rapier's second roll 25

(Nevermind on the advantage, they're both worse than the original rolls)

Scimitar's second roll 7

(Yup, there are stairs leading up to you and there on both sides of the inner railings. The crew pirates are currently  equipped with scimitars and is 60 feet away. And I misread LaRue's post and did not mean to put her there. Since she did move and went for cover, she should be by the mast and technically right by the crew pirates. And Lilliana does have advantage if for the wisdom save)

Nate's rapier does a shallow pierce into her while the scimitar seemingly bounces off her feathers. She notices and looks over to Nate, pointing one blade to him.

(Roll for initiative.)

(OOC: im guessing that Gaèl would not have managed to draw both of his swords? Edit: Oh wow.)

Initiative: 4

Initiative: 20

OOC: Not counting the Aarakocra, how many pirate crew members? Also, if I had time to move Lilli to cover, you probably could draw both, Vyr.

Initiative - 4

Lilliana allows herself to be escorted by Aiden, still shaking from the terror of her near-death experience. Her hands dart out and clutch the inner-railing after he pries his hands away and she stares down at the deck, trying not at all to look near the outer railings...

Wisdom Save - DC10 9

This die roller really seems to hate Lilliana lol.

Nate points his own blade at her.

Initiative 4

(Jesus Christ, that's three natural ones for the party)

OOC: It seems I will be going first, so I will go ahead and roll my turn. Got an appointment to get to and I'm not sure what time I will be back to check on this.

With the pirates 60ft away and closing, Aidan will attempt to hide behind any crates, railing, or stacks of supplies that he can, waiting for the aggressors to close the distance.

Action: Hide

Stealth Roll: 10

(Well that roll sucked...)

Edit: If you rule there is nothing behind which he can hide, he will simply take cover at the railing and hold his action to throw a dagger when an enemy comes into effective range.

Initiative: 12

(I'll still be using Toll the Dead when the time comes.)

(So what's the initiative order?)

Order:

1. Aiden
2. Red
3. Aarakocra
4. Gaèl
5. Lilliana
6. Nate
7. Pirates

Held Action: Throw dagger at target in effective range.

Attack Roll: 5 Damage: 5 piercing plus 6 sneak attack (If applicable).

(Still trying to maintain cover as much as possible.)

Edit: (Well that stinks...)

OOC: Virst? 

(For Liana's turn.)

Liana continues to hold her action until one of the pirates are injured. Readying her toll of the dead.

(For Aarakocra)

The Aarakocra whispers a word as a wind sort of comes around her as she dashes off to the man, striking at him.

Attack: 25 Damage: 8

 The man manages to parry the bird woman as he points his blade back in protest.

(Does Nate get an AoO since he was within five feet of her? If yes)

AoO 18 Damage 4

For his turn, Nate will say, "Oh no you don't," get around her to flank with the guard, and attack. 

Rapier 15 Damage 6

Scimitar 25 Damage 6

(Dang it, you know.)