(Drats! Time for Plan Delta for when his turn comes around!)

Initiative: 1.

(... eventually)

While still clasping his bucket, Nobody will crawl his way over to the main mast, struggle back to his feet, and using both it and his tail. 

"That... Gond help me.... That... was a warning shot. Now shoo."

He calls out with a voice still amplified by the spell.

(I'm should just go ahead and give him disadvantage at this point, right?)

Nobody tries to talk, but bile is all that comes out. Gynugri does a fancy magic trick as he slinks into the darkness and a small fog cloud appears in his hand.

(While we're waiting, I'll post my next turn.  What's the pirate's initiative?)

Melanthios will pop up above the railing, shoot his target once more, and drop back down (from now on, to avoid confusion, I'll call shots modified by Sharpshooter "piercing" attacks.)

Piercing Attack: 10 Damage: 20

Just realized something: are the pirates coming closer and going to be here within one turn?  If so, Melanthios will instead Hide: 24

(I perfectly understand if you hold me to my previous action, given my attack roll)

 Initiative: 17

Gene will go to the opposite end of the ship compared to the direction the threat is approaching from and will take up a fairly secure position there.

If she's within earshot, Tab will call out to the Captain:

"Ortimay! How far to Chult? Can we outrun them?"

(I'm a little confused about the order of things.  How many rounds have passed?)

(Just the one by my reckoning. Though the pirates haven't gotten a chance to move yet. And the same goes for our npc crewman)

(Sounds about right.)

"I doubt we'll be able to outrun them. Get ready to fight! Oh, and do try and capture the captain, Chult offers a pretty penny for any pirate captain captured."

She then stands down from the wheel and draws her scimitars, letting the pirates advance. The other sailors do likewise. 

YOU GUYS HAVE ONE MORE ROUND BEFORE THE PIRATES ARRIVE. WHAT'LL YOU DO?

Quote from LordShadowthorn >>

(While we're waiting, I'll post my next turn.  What's the pirate's initiative?)

Melanthios will pop up above the railing, shoot his target once more, and drop back down (from now on, to avoid confusion, I'll call shots modified by Sharpshooter "piercing" attacks.)

Piercing Attack: 10 Damage: 20

Just realized something: are the pirates coming closer and going to be here within one turn?  If so, Melanthios will instead Hide: 24

(I perfectly understand if you hold me to my previous action, given my attack roll)

 Here we are :)

Tab looks up, seeing the mast looming up above him. Seeking a higher vantage point, he pops his claws out with a subtle "snikt" sound, and climbs up to the yardarm, slinking along in the direction of the inbound ship. (Tab has a climb speed of 20 ft.) He will then wait until the boarding action begins, and try to leap/tackle someone important looking. Acrobatics: 17

From the darkness, Gynugri prepares himself the same frosty spell on his hands, ready to be unleashed at any suspecting pirate he can reach from his position.

Nobody groans pathetically into his bucket. If he could but muster the wherewithal this time, he'll take one look at the climbing Tab... and just chuckle hysterically as he made his way over to the wheel. "Just... ohh... don't mind me captain. Just..." He has to cover his mouth for a second. "Ugh... Just don't mind." Is all he can manage before pressing on to peer past the edge of the ship. 

If he can manage it, he holds his staff up high and try to hold onto to sleep meant to catch the largest cluster either in transit to board their ship. 

YEAH, YOU CAN GO. ROLL FOR SLEEP SLEEPINESS.

(So did I make the attack or am I stealthing?)

Sleep: 26.

Gene will let an arrow fly towards one of the non-sleeping enemies: Attack: 10 Damage: 11

(@LordShadowthorn I'll let you make the attack, then stealth, since you didn't realize you had an extra round(sorry for not telling you that))

(Oh, ok.)

(Side note: my phone just tried to autocorrect ok to Og . . .)

(Lol! That is awesome.)