Ankita is taken aback by the cost they want to charge them just to take a couple days off their journey?  And Jolly sure doesn't seem too Jolly!  And what was with the smirk?  Olaerys seems to know what he's doing, so she decides to follow his lead.  

Holger leads you to a reasonable sized boat. The captain is a blue skinned genasi named Shoalar. He looks at you with askance but a glance at Holger settles him.

"Alright then, Beliard it is. All aboard friends! Pike! Get the boat ready. Time to set sail"

Before we reach the dock and the boat, in a relatively quiet section of the walk with Holger, Olaerys says “Holger, I thank you for your hospitality but we really do not have deep purses.  We could offer 10 gold for the group of us to go up river and I think that is a fair price, but 10 each is too much, we just can’t afford it.  We could walk there, but since you have a boat already going so it does make sense… Can you help us here?  What do you say?”  He touches to arm of Shrek and makes a thumbs up and gives a big toothy grin to Holger, hoping to convince him.  

(Rolling with help from Shrek, Persuasion : 16 

Holger looks around to make sure no one's watching. "I'm not in the bloody charity business, and what do I bloody tell Jolly when I'm light on the gold? " He thinks for a second and smiles. "Ok. Here's the bloody deal. I hate that damn genasi. 20 gold and I'll put you on the bloody boat. I'll tell bloody Shoalar to collect the rest when you reach Beliard. All you need to do is refuse to pay him. He might get violent, but he's not something the likes of that big fella can't handle", nodding at Shrek. "I get gold, you get bloody Beliard, and bloody Shoalar gets knocked down a peg. Win all around."

Randall just watches Olaerys work out the deal.  He had been prepared to pay the 10gp without further complaint... it felt expensive, but he had no idea what the going rate was for armed fighting groups providing boat transport to other armed fighting groups.

This entire visit to this fort has seemed incredibly tense, but he cannot put his finger on what is going on.  He makes a mental note to ask Olaerys and the other about all of this once they reach Beliard.

"Honestly, it looked like Jolly was going to have us bloodied by the end of the trip anyways, works for me." Ankita adds.  Though she is realizing she might be in for more than she bargained for when she offered to assist.  Well, in for a penny, in for a pound.  

Olaerys keeps talking to Holger, walking toward the dock.  After the offer is made, he makes a point of giving the gold to Holger and having this observed by the crew on the ship, including the captain.  "Fine, you have a deal.  The deal is the deal.  More expensive than we wanted, but we are in need of transport."  

He walks out to the boat and climbs aboard with the crew, ready to head to Beliard.  If approached by the Captain, he will inform him that the price for the trip has already been paid.

Shrek follows Olaery's onboard the boat, but remains alert to any shenanigans the entire trip (Perception: 18), making sure to never let his guard down, not fully trusting the crew and captain.

But fails miserably.  In fact, he quickly falls asleep due to exhaustion from the hike and observing the negotiations, wracking his two brain cells trying to follow along...

The large keelboat is moored to the inner side of the keep’s east wall, floating in the boat basin. A rope ladder leads from the top of the wall to the deck of the boat, about six feet below. Hatchways lead into the boat’s cabin from the bow and the stern.

At Shoalar's command, a halfling appears from somewhere and begins to prepare the boat to leave. Shoalar has a quick word with Holger, and turns to you, looking at you in an odd way, paying particular attention to Melchor. "Should be about a 5-6 hour trip. I'll get you there by midnight." The boat pushes off shortly later and you are on your way!

DM check: 15

2 hours later, dusk settling in, you hear Shoalar whistle and the boat drifts to a near stop in the middle of the wide river. His voice booms, unnaturally loud, and two 

"Pirates! Best be ready to fight. They won't just stop at Pike and I."

As he does you see a large keelboat blocking the way up river, preparing to board you.

DM rolls:

 A quick count is concerning, as there are more than 10 pirates you can see.

Crud. 

His heavy chainmail armor makes a tactical retreat to shore out of the question.  Randall draws his spear and huddles up with his allies to prepare to defend themselves and their ship.

Ankita's eyes open wide as she looks at the foes about to board their boat.  She glances around wildly and figures to herself, yep, we're trapped on a boat.  Great.

(Assuming the boat is within 90', otherwise disregard this next bit)

She calms herself and refocuses.  Ankita lifts her quarterstaff up and holds it horizontally.  She speaks a few words under her breath and casts entangle in the middle of the pirates from where she can see, hoping to slow them down, or scare them enough to let them pass.

For DM:

‘We can’t let them board us…’ Melchor warns, as he prepares a flaming chromatic orb to cast at the boat containing the pirates, as soon as it comes within 90feet….

Quote from JorvikDave >>

For DM:

When Shoalar was checking Melchor out, did he get the impression this might be another outpost of his erstwhile colleagues?

‘We can’t let them board us…’ Melchor warns, as he prepares a flaming chromatic orb to cast at the boat containing the pirates, as soon as it comes within 90feet….

Olaerys has his shield out, crouched down below the gunwale on the deck, watching the approaching vessel.  “Looks like our ride got a little more interesting” he says to the Captain.  He readies a javelin to hurl at the first target visible, when they are within 30 feet.  

Shrek wakes from his unscheduled nap to a large amount of commotion onboard the boat.  "Huh?  Whoza-wuzza-what's goin' on?!"

Rubbing the sleep from his eyes, he sees Melchor towering over him, with a ball of colorful electricity sizzling around his hands.  Taking a handful of seconds to come-to, he finally realizes what's going on.  "We's under attack?!" he calls out to his compatriots.

He quickly rolls over and peers over the gunwale to apprise himself of the tactical situation.  That's when he finally notices the pirate ship.

A little late on the draw, he mirrors Olaerys by unclasping a javelin from his back quiver, and waits to see how the situation unfolds.

As the boat approaches, Shoalar makes a dramatic gesture with his arms and a huge wave appears out of nowhere and quickly swamps the craft. Pike, the halfling, laughs maniacally.

DM rolls: 

15

 When the wave passes you see 1 pirate missing. 2-3 are picking themselves up, as is what appears to be the captain

2 pirates, unmoved by the wave, fire crossbows at Shoalar, embedding in him but not seeming to bother him

Attack: 12 Damage: 2

Attack: 7 Damage: 9

The boat is now at 90 feet away. All player turns are up. (Melchor, specify a target).

Randall will dodge any incoming bolts this round, and will use his reaction the first time an ally within 5ft is attacked to impose disadvantage on that attack (protection fighting style).

As posted above...  now that the boat is within 90 feet..

She calms herself and refocuses.  Ankita lifts her quarterstaff up and holds it horizontally.  She speaks a few words under her breath and casts entangle in the middle of the pirates from where she can see, hoping to slow them down, or scare them enough to let them pass.

(Sorry if I wasn’t clear, Melchor was targeting the boat itself - i.e. trying to set the boat on fire… If it’s too wet/waterlogged after the wave he’ll cast at the Captain..) 

Attack: 22 Damage: 13 Fire Damage