Does an Insight: 19 reveal anything about the crew?  

You heard Lazar bark commands and they all seem to be rushing toward the front of the boat with some serious purpose - presumably to try and save themselves from whatever this gargantuan creatures is that seems hellbent on smashing the boat.

After watching in horror as Brask was flung off the ship, Kurama saw Effort running towards the front of the ship and called out to stopped her.  "Effort!  Use the other boat at the back!  I'll find Brask!"  Before hearing a reply, he rushed to the edge of the boat and leaned over the rail in an attempt to find the minotaur.  If he caught sight of him at all, he'd foolishly jump into water after him.

Perception: 27 (NAT 20!!)

It's probably really dumb to have Kurama jump in the water, but it's what he'd do XD

You see the tips of two horns poking above the surface. Keying in on that spot, you eventually see Brask's head come up for air. He thrashes about, bobbing beneath the surface again. Kurama, you dive in after him and, using your dash, can make it about 2/3rds of the way to your furry friend.

Brask, you're up. You're not actively drowning, but you (I'm guessing) aren't the most confident swimmer either. As you come up sucking for air, you see Kurama splashing through the water heading toward you. In the distance, you can see the outline of the boat surrounded by the massive tentacles that absolutely dwarf it. Despite the fact that you all might die here, the silhouette is pretty bad-ass.

Brask isn't an experienced swimmer, but he has some powerful strokes and isn't too troubled by the situation he finds himself in.  He's definitely glad of his extensive training with heavy armour.  He swims towards Kurama and the boat as fast as he can.

If needed:  Athletics 17

You reach Kurama after a few moments. In the distance, you can hear wood snapping as the creature's body slowly begins to push up against the bottom of the ship. 

A few members of the crew reach the front of the boat and pull on a pair of levers. The forecastle of the ship partly opens up, revealing a smaller boat built into the front of the vessel. Lazar appears from his quarters carrying two big sacks over his shoulders. He throws them into the boat and yells something at the crew. It's inaudible as one of the tentacles smashes down again onto the deck. This time a huge chunk is broken off, falling into the water as rushing sea begins to fill the exposed rooms below deck.

Pip and Effort struggle for a moment to maintain their footing. Pip eventually reaches the back of the ship, grabbing one of the ropes tied to the trailing skiff.

The sky has grown noticeably dark overhead, and you can see little flashes of lightning buried within the gray and black sky.

Effort, you're up.

Effort orders Cadmael to track Brask and Kurama.  Staggering, she abandons her play for the crew's skiff and makes her way over to Pip instead (if she can).  "Hold fast to me!" she yells, unwilling to leave the little goblin behind.

(If Effort can reach Pip, she'll cast guidance on him.  If she can't reach Pip, she'll dash until she can.)

You can certainly reach Pip on your turn. 

Pip leaps up, still with one eye on the ocean trying to keep watch over the others.

Effort hisses, using her action to lash a rope around Pip's waist and connect it to her own.  There's some give, so the goblin can still move a bit freely, but enough so that they can't be separated should the ship shudder and lurch, at least not without severing the rope with a dagger.

Kurama & Brask, you guys are up out on the open sea! I am guessing you'll keep swimming but LMK if there's anything else you would like to do.

Yup, Kurama is swimming towards Effort, Pip and the Boat!  As he makes his way over to them, can he tell how the rest of the crew is fairing?  (11 Perception if needed)  

You see motion toward the front half of the boat as the entire thing is slowly starting to tip from the gushing seawater, but you can't focus for too long as you're trying to keep your head above the waves and swim closer.

(I don't know if we're still in turn order, but...)

"Pip, we need to get to the other skiff," Effort says as the boat begins to tilt dangerously.  "Are you ready to let go and run?"

Brask is swimming mightily towards wherever Kurama, Effort and Pip are.

Pip nervously nods, starting toward the back of the boat as he keeps turning his head to look over the side toward Brask and Kurama. 

The storm clouds darken further, and as the beast raises its enormous tentacles into the sky, three stark lightning bolts shoot down toward the ship. As they strike, the middle section of the ship is completely blown apart, sending both halves lurching either way. The clouds slowly funnel downward, making things even more difficult to see.

Effort & Pip, make DEX-saving throws as you try to avoid shrapnel and keep whatever footing is possible! Pip: 6

Brask & Kurama, make DEX-saving throws as well to avoid the bits of ship splashing down into the water.

Kurama DEX Save: 16  (Let me know if he needs to roll with disadvantage (or advantage etc.) Due to being in the water

Brask's DEX save: 9

Just need one from Effort.

Straight roll is fine, Kurama. Never ask for disadvantage! Haha.

Haha too true!! I've just been DMing too much lately XD

(sorry, had a very busy week, Effort got a 9 :O )