Gerrard forces the door open with his shoulder, and quickly discovers what was holding the door shut: webs. Sheets of webbing fill this room. You can barely see ten feet into this cabin through the thick webs. 

Gerrard:

Backing off and drawing his rapier, Gerrard looks to Peri, saying, "Want to go fishing for webs again, Master Fenwader?"

Peri:

((Somehow missed the above post so I'll change mine, but I thought it was funny so I'll put the original in the spoiler block below.))

 Imagining the number of spiders that could be living in that much webbing sets Peri's skin crawling. He prepares to once again heave the grappling hook into the webs and begin the work of clearing them. "I'd set the whole blasted mess on fire if I didn't think it'd burn down the ship. D'you think you could make a controlled burn in this mess, Mr. Fiercehammer?"

The door has indeed been forced open. Nothing but webs impedes you now.

Gerrard:

As before, Gerrard keeps guard at the side of the door as Peri dredges out the webs.  With his glowing rapier drawn, the young noble agrees over his shoulder, "Yes, fire would be perfect to clear out these webs if we didn't have to worry about burning down the ship and us with it."

Kei 

(Short rest 3 x HD 22)

The rest brings a little relief to the battered bard. He rises and gingerly follows the others back up to the main deck. The near death experience still at the front of his mind, he falls in behind Gerrard. Although a few steps further back than last time. "Does taking the brunt of an ambush repay my debt to you young noble?" he asks with a chuckle. "Either way, I still have your back. I just hope the next monster doesn't want to eat mine."

HD again24

((Worked now so I'll take the original roll))

Peri fetches his sticky grappling hook and begins to clear the initial portion of the cabin - enough for some of you to step inside.

These webs are different - thick and opaque, but not sticky. They don't impede movement, just visibility. Peri makes quick work of what's in front of him.

Stepping inside, Gerrard and Kei can see what looks like it might be a hole in the deck or a narrow staircase, to port.
To starboard, Peri can see battered furniture, including a chair of some sort, clotted with webs, as well as a heap of garbage or debris.

The floor is split and spongy here. There's no immediate collapse danger in your immediate area - just a mildewy porousness to the decking. 

Gerrard:

Sweeping his blade out in front of him, Gerrard moves forward and points it down the hole, wary of any more spiders that might come rushing out.  He keeps an eye out for other movement in the webs around him as best he can as well.

Perception:  8

(Edited to force roll to resolve)

Gerrard approaches the hole, find that his blade is just as effective against these webs as Peri's hook. It turns out to be a narrow staircase down. Gerrard sees nothing at the bottom of the stairs - just more worn decking. All is quiet.

Gerrard:

"Let's get all the webbing down in this room so we hopefully won't get jumped by anything else hiding in the debris," suggests Gerrard, suiting action to words and moving around the cabin clearing the webs, keeping an eye out for any more hidden bugs waiting to jump out from cover.

Perception:  8

Quote from Mithdraugaer >>

Peri:

((Somehow missed the above post so I'll change mine, but I thought it was funny so I'll put the original in the spoiler block below.))

Peri watches Gerrard struggle with the door for a bit before offering him the crowbar that he has, in fact, given him in the past. "Very wise, Lord Feldren. Someone certainly should carry a crowbar." If Gerrard can't pry the door open, Peri can fire a couple of eldritch blasts into the lock and let the lordling try again.

 Imagining the number of spiders that could be living in that much webbing sets Peri's skin crawling. He prepares to once again heave the grappling hook into the webs and begin the work of clearing them. "I'd set the whole blasted mess on fire if I didn't think it'd burn down the ship. D'you think you could make a controlled burn in this mess, Mr. Fiercehammer?"

 Dwal
"If'n we go slow I can use fire to burn them bit by bit."
Dwal will use his torch to burn the flames then use Control Flames to control the burn and guide the flames to burn the webs away. If the flames start to get out of control Dwal will use Control Flames to extinguish the flames.

Gerrard:

Once they have cleared the webs and searched the room, Gerrard prepares to lead the way down the steps again, saying, "Maybe follow a few more steps behind this time, Kei.  I'm sure to need your aid at some point soon, and I want you to be healthy enough to deliver it."

Investigation in the current room as the webs are cleared:  13

Perception (including looking on the ceiling this time) after going down the steps:  6

Kei 

Drawing his short sword he follows the lead of Gerrard, swinging wide while keeping an eye on the room.

Perception 12

As the last of the web's come down he stows the simple tool and fingers through his component pouch making a mental note of what remains. He swings the cittern over his shoulder and holds it by the neck. It looks somewhat like a stringed club in his hand.

"Ready when you are Gerry. I'll try not to get eaten this time. Wasn't particularly enjoyable." He takes a step back from Gerrard, and then another half step - just in case.

Gerrard, Peri, and Kei systematically begin to clear out the webs in the cabin, as Dwal burns them away (an equally effective, if smellier, approach.)

Kei spots it first: a table still covered with charts and maps ...and a pair of large insect eyes well-hidden in the webbing and shadows on the ceiling above it.

(Roll initiative if you want to engage it, or if you want to examine or take a map...)

Gerrard:

As soon as he sees another spider, Gerrard says, "Ugh, another spider infests this cabin.  I'll take care of it."

With his rapier out already providing light, Gerrard prepares to draw his Main Gauche and engage the creature.

Initiative:  19

(Here we go!)

Initiative:
Gerrard:  10
Big bug: 8
Kei: 11
Peri: 11
Dwal: 19
Bjorn: 16
Oceanus: 5
The OTHER big bug (Giant Spider): 4

Gerrard approaches the insect eyes in the ceiling with his rapier drawn.
What he doesn't see - and in fact all of you miss until it's too late - is the OTHER massive spider hiding nearby on the ceiling. It surprises all of you.

Giant Spider Bite Attack vs. Gerrard: 20  Piercing damage: 5 (on a hit, Gerrard must make a DC 11 Constitution saving throw, taking 10 poison damage on a failed save, or half as much damage on a successful one.)

Gerrard may respond to the first attack if he has a reaction or something, but then Dwal may act next.

Reordered initiative:
Dwal: 19
Big bug Gerrard is after: 18
Bjorn: 16
Kei: 15
Sneaky Giant Spider: 15
Peri:  4   11
Gerrard: 10
Oceanus: 5

Gerrard:

Barely getting his blades up in time to block the spider, Gerrard manages to throw off its aim just enough that its dripping mandibles scrape off his armor with a loud screech but do not find purchase in his flesh!

Peri:

((Initiative is technically an ability check, so I'd like to use that sweet, sweet Luck o' the Halflings to try it again: 22))

((And it made effectively zero difference...))

Dwal may act next.