Eventually convincing Jolly to allow them a test run as new recruits, the PCs bunk up in Riverguard Keep. The next morning, they are split into two groups to help man the two vessels captained by their ol' pal Shoalar Quanderil, the genasi, and his first mate, a halfling. The remaining crew was made up of pirate brigands from the keep, equipped with sharktooth longswords and crab shell shields. Oh, and one passenger with red-tinted skin and a mysterious air about him.
Once upon the wide Dessarin River, the two keelboats were directed to approach a merchant vessel. Demanding protection money, Shoalar quickly lost patience with the desolate crew and ordered the new recruits to kill them. Although Vorganth was quick to unsheath his great sword, Sparrow quickly boarded and attempted to convince Shoalar they had the money after all. Whether he thought he crew liars, hold-backs, or just fell prey to his pirate instincts, the execution order stayed. As the PCs hesitated, Shoalar's hunch was confirmed and he ordered the attack.
With Sparrow on the merchant vessel, Buskin faced four pirates and the halfling. He quickly scrambled to the merchant vessel for higher ground and some friendly faces. Goodbelly and Vorganth challenged Sholar directly on the second vessel, but not after Vorganth connected with the red-skinned one and forced him to cast a defensive mirror image. Devastating attacks by Vorganth and Goodbelly quickly took the smirk and mirth from Shoalar, and he fell dead early in the combat.
As Buskin and Sparrow tangoed with the pirates now on board the merchant ship, the red-skinned mercenary surprisingly turned on his fellows, casting a shower of electricity onto the halfling's boat, causing damage all around and the ship to catch fire. Vorganth looked a bit confused, but the mysterious humanoid retreated to the larger boat as well.
With pirates clawing to get off the burning keelboat, Vorganth leapt the distance between the two and joined the fray. In the meantime, Goodbelly shockingly melded into the form of a panther and squeezed in between Buskin and Sparrow on the main ship's deck. Witnesses disagree as to whether Newt the badger may or may not have been riding the panther, in the known T-rex/shark style:
Despite struggling to find purchase on the rocking boat and connect with many attacks, Buskin's intimidating manner caused at least one pirate to flee and was nearly taken down in his ill-fated escape attempt. Although Buskin and Sparrow surely would have handled the 'situation', Goodbelly the panther, Vorganth in a rear position, and the 'red one' from a distance helped finish the group, leaving one prisoner alive.
The mercenary Sharis (red one) hinted at being in an unfavorable position with Jolly's crew and offered up helpful information to the group. With the help of Sparrow's suggestion on the prisoner, the PCs decided to take the merchant wares and sink the ship. Employing a ruse to re-enter Riverguard Keep, they eventually convinced Jolly the 'surprise attack' cost the lives of his men. The testimony of the one remaining pirate ultimately eased his suspicion.
Knowing the remaining Dwarven books from the Mirabar caravan were most likely located in the keep chapel, the group immediately ventured inside to investigate. Two door guards and two bodyguards to the priestess Drosnin eyed the group as they attempted to chat up the holy woman. Their words were quickly drowned out by her oratory, with no end in site. Goodbelly successfully sneaked up the side of the aisle behind a bodyguard and identified more Dwarven books on the shelves.
Sharis attempted to discretely cast sleep on the priestess, and although she continued to preach loudly, both pirates near her collapsed to ground, asleep. Goodbelly felt his eyes droop a little, but quickly shook it off. After seeing the door guards start to run up behind the PCs, realization dawned on the priestess. Initiative!!
EDIT: Retcon to correct our misapplication of sleep. Lowest HP characters (including PCs) are affected first.