Peri:

"I don't know how you expect to get answers without takin' the ship? I figure the Council's payin' us to take out the smugglers, and the best way t'do that is to sink or burn the ship. Might be our best course is to hit it from a buncha directions all at once." He then throws out a plan in which Gerrard starts boring holes in the hull, and Peri summons an Unseen Servant to pour oil on the rigging and sails. As soon as the crew raises the alarm about the leaks, Gerrard can try to Gust it aground, and when the crew tries trimming the sails one of them can torch them. Then the party can board the ship in the chaos, hopefully causing enough confusion that the ship either sinks, burns, or grounds. 

Gerrard:

”I’ll defer to your experience,” says Gerrard, grabbing the drill and peering through the darkness to try and see what he can discern about the smuggler ship.

Perception:  16

You survey the situation:

Gerrard deduces that Gust of Wind is unlikely to push the ship completely ashore, but the force of its impact could definitely add to the chaos of the moment, if needed.

The boat does not appear to be anchored right now – that could change at any moment – but Peri knows that a ship this size likely would use a pretty hefty chain, not a rope, and a capstan, maybe even winch-operated. So it would be very difficult to cut the chain with the tools you have; you'd need to get aboard to raise the chain. But right now it is unanchored and drifting slightly, the sail luffing in the breeze.

The hull looks wet and slimy and slippery, but appears to have a number of potential footholds for scaling. On the other hand, everything looks too wet to burn easily; in addition to oil, you'd need some dry kindling of some sort to really attempt to burn it to the waterline. But of course, burning oil, even on a damp surface, could make a great distraction.

Holing: it's likely that drilling holes in the hull - or even chopping it with an axe - would potentially result in a sinking that would be measured in hours, not minutes.

Peri makes out a figure in the crow's nest, but it appears to be facing the shore, not the Stone. 

You see a faint blinking light - somebody on the aft near the tiller is attempting to signal the shore with a lantern, most likely. Long–short–short–short, it blinks.

Gerrard:

After assessing the situation, Gerrard says, "On second thought, drilling the hole might take a long time for them to notice, so it may not be the best distraction.  As it isn't anchored right now, perhaps climbing up the side and attacking with flaming oil, wind gusts, and weapons might be a better approach--those of us who can't throw fire from afar anyway."  But the drill is still in his hand, and Gerrard adds, "but if you still think it best, I am ready with the drill Master Fenwader."

((A powerful outside force -- perhaps the voice of Brandobaris himself! -- is telling me the holes will do no good, and the rigging won't burn. Those were my best ideas.  Anyone else have a plan that isn't "jump over the side and hope for the best?"))

(OOC: Don't let the DM whisper in your ear! The dice will have a lot to say in the matter. Try whatever you think might be fun!)

Gerrard:

OOC:  If it helps, Gerrard just wants to do things that are 1) effective, and 2) will make a suitably heroic story later when he is wooing the fair Lady Esmerelda.  Spending 10+ minutes trying to bore a small hole below the water line in a big ship while treading water seems pretty miserable, but jumping around with a rapier in one hand and a magic fan in the other while alternating stabbing the smugglers or simply blasting them overboard with wind gusts sounds like more fun.

The ship appears to flash the signal again. Fossie is getting anxious, shifting her weight rapidly from foot to foot. "They're prob'ly gonna leave soon. Time to act. You wan' me to come alongside it? I can sail most 'o the way, but I'll need your help with the oars when we get close. Maybe they won' see us if we come up on their starboard. Everybody seems to be lookin' at the shore." How she can see that in the near total darkness is a bit of a mystery, though. Those of you with darkvision or devil's sight can barely make out a handful of figures on deck.

Gerrard:

"Yes, let's go now!" whispers Gerrard excitedly, not wanting to miss their opportunity.  Attacking from behind while everyone was looking towards shore, then causing what distractions they can once on board seemed like the right call...

Fossie pulls on the halyard and you begin moving forward again. She tacks her way within a hundred feet of the seaward side of the smuggler vessel. She quickly and quietly comes about into the wind and lowers the sail. She pantomimes for the four of you to grab an oar and row the rest of the way.

So far, so good - there's no indication that you've been spotted, yet. You hear a voice shout an order on the deck, but you cannot make out the words.

You count at least six figures on the top deck - two on the (central) Main Deck, one on the Forecastle (bow), and three on the Poop Deck (stern) including the sailor with the lantern.

Dwal

Dwal grabs a oar as quietly as he can, knifes it in the water gently and rows. 

"Gonna be a climb and I'm crap for climbing.' he thinks to himself. 

Once the smaller craft pulls along side Dwal looks for a dangling rope or hand holds along the side or even a ladder.

Investigation: 20

Peri:

Before taking up his oar, Peri will pull a rope and his oil flasks from his pack. He ties a loop into the end of the rope and arranges it and the flasks at his feet. Then he will quietly pull his oar until they near the ship. 

He stows the oar, then uses his mage hand to carry the loop up to the gunwhale and hook it over a convenient bollard. He will quietly summon an unseen servant and direct it to carry the oil flasks up to the sails and begin soaking them in oil.

There are handholds visible, but they are wet and slimy and somewhat slippery-looking. No ropes, but you see where a rope ladder is likely coiled up on the deck.

The vessel stands about nine feet above the waterline to the top of its main deck rails.

The sound of the waves and sea is quite loud, but you can hear a thick voice calling out, "I don' like this!"

Gerrard

Rowing quietly as well, Gerrard makes sure the fan and his weapons are close at hand...If they can get the drop on the smugglers, a well-aimed wind blast might send a few into the drink.  He waits anxiously for the rope to be ready and for Peri's indication that he is ready for Gerrard to go.  Once he gets the go-ahead, he tries to slowly and quietly climb up the side of the boat using the rope.

Athletics:  22

Gerrard:

Assuming that works, Gerrard drops the rope ladder quietly over the railing behind him and waits for the others to be ready.  He has the fan at the ready, planning to activate it and blow some smugglers overboard if he can before they can react, but he holds his action as long as the enemy doesn't see him (to give the others time to ascend).

He stows the oar, then uses his mage hand to carry the loop up to the gunwhale and hook it over a convenient bollard. He will quietly summon an unseen servant and direct it to carry the oil flasks up to the sails and begin soaking them in oil.

Peri carries out both of these tasks quickly and quietly – you watch as both the rope and the oil flasks levitate independently up into the air. The rope is soon neatly looped to a cleat on the main deck - just about at the midpoint of the ship. You can barely make out the oil running down the canvas sails in the inky darkness above.

Gerrard deftly climbs the rope, and peers over the side. Though the light is very dim, you can see details of the ship’s main deck. In the center, forward of the mast, a jolly boat is lashed to the deck with ropes. Aft of the mast is a hatch to the belowdecks area and a rope ladder climbing to a crow’s nest above. Two human figures lean against the rail mid-deck, staring toward the coast. To fore and aft, below the upper decks, stand vague outlines of doors. You can also see ladders that lead to the upper decks, the aft one on the port side, the forward one on the starboard.

A gruff-looking man with a longsword and wiry teenager with a scimitar look shoreward. A small amount of light spills out of the hatch leading belowdecks. Gerrard quietly pulls the rope ladder toward him and lets it fall down the side, toward the Stone.

Peri:

He silently prays to Brandobaris, asking the Trickster for a bit of luck, then takes up his spear and quietly climbs the rope ladder.  He clears the rail and slides to the right (toward the forecastle) to make room for the dwarves.  He crouches, ready to spring forward at the first cry of alarm.  He will also direct his unseen servant to the base of the mast, near the belowdecks hatch.

Qivys

As the smaller boat pulls alongside, Qiv stops his humming. Infact his mood becomes much more serious. He watches as Gerrard virtually runs up the side of the boat with little help from the dangling rope. Stowing his Warhammer and slinging his shield on his back he spots into both hands and runs them together. Quietly he whispers to Dwal "See you up there brother". He ascends the rope ladder somewhat elegantly and clears the top rail. He shuffles to the left as he silently draws a dagger and releases his shield from its clasp.

Athletics 15

Dwal

As quietly as his clumsy feet allow Dwal will ascend the latter last. Once up top he will attempt to be silent and prepare himself for what is to come.

"When they come, form and hold the line." he whispers.

Dwal will then move to where he hears the voices of the pirates/slavers are, trying to stay just out of their light. If he is spotted he will make no pretenses or faints he will hold shield and hammer in the ready position.