As you approach a small, wooden dock you see a Keelboat waiting for you. A fish-folk (Lacathah) crew member is wrapping a thick rope as he looks up and waves a webbed hand.

Ugly Beard yells in his direction. "Prepare to set sail, fish-lips!" As you approach the Keelboat you can see that this ship has seen its fair share of voyages. Ugly Beard motions you to climb aboard. "Prepare your sea-legs, land lubbers!" 

The Salty Mermaid

https://www.dndbeyond.com/vehicles/keelboat

Ugly Beard's crew member: Heartless Fish

Pandew

Pandew snaps to and says "Aye Captain! What position do you want to be be at?" he asks. 

Ugly Beard, distracted with his booze, exclaims: "Prepare to set sail, fish-boy!" Pointing his cutlass into the air and taking a swig from a bottle. Heartless Fish pushes the boat away from the shore with a worn wooden oar...

Pandew

Pandew will grab another oar and help shove off then paddle out of the bay if that is the plan. 

The large wooden vessel moves slowly away from the small wooden dock. Pandew and Fish row casually. It's a bright sunny day and it's still morning. The keelboat has a door at the back, leading to the captain's quarters perhaps. There are a few rows of benches and a few oars as well. At the front of the boat, a ballista. There are 10 rounds of ammunition lying on the ground beside it. A single sail starts to propel you slightly faster as the wind picks up. There are a few crates and barrels scattered around the ship. Ugly Beard looks at Pandew, offering him the bottle, "Aye! Care for some fire in your belly?!" Ugly Beard lets out a gutteral laugh. 

Pandew

"I do not drink" Pandew says. 

Pandew turns to his task then looks out to the Ocean and he feels peace.

His peace is interrupted by a loud and sudden commotion... Ugly Beard lets out a blood-curdling scream as he rushes to the side of the ship, "Shark!" He points toward the port side of the ship as a giant fin raises out of the water. Heartless Fish bellows out a bubble-filled gasp as he begins to frantically row faster. Ugly Beard takes a long drink out of his bottle, racing for the ship's wheel. He yells towards Pandew, "Load the ballistas land-lubber! It's high time we break you in!" 

ROLL FOR INITIATIVE. 

Pandew 

Pandew rushes to one of the ballista's and tries to load one. If he does get it loaded he will try to track the shark.

Ugly Beard 17

Heartless Fish 7

Giant Shark 16

Initiative: 5

Heartless Fish stands up and runs to the side of the ship as he grabs his spear and stabs at the beast, just as the shark submerges itself under the water... 

Spear Attack 1

 He loses his grip as the spear plummets into the water and sinks. 

Ugly Beard yells out, "Is that all you got?! Do something fishboy! We're under attack!" 

He spins the wheel and the boat turns violently away from the shark. 

Everyone not steering the boat or manning a ballista must make a Dexterity Saving Throw or fall to the deck, prone and your weapon falls out of your hand. DC 10. 

Heartless Fish 3

Wait? Am I doing this right? HAHA Or did the fish really just roll two one's in a row?! HAHAHA 

Testing 15

Oh my... he did.

Heartless Fish loses his footing (finning?) and tumbles over the side of the ship. 

Ugly Beard screams, "Fishface! No!" As he takes a swig out of the bottle. 

All is silent... you hear not a thing...