DragonDenn’s Theros Game

For the upper deck... Yes Casseopeia managed to get between the hatch and the captain. The captain has moved to the further end of the boat, near the wheel, which is about 40 feet from the hatch you are near. He started that way as soon as the others started down the ladder. There is a mast, with some crates near it, between you and the captain. There is no other entrance, that you can see anyway, into the lower deck, other than the hatch the others went down.

Ritha give me an athletics check, to carry Io up the ladder and to the upper deck. This is a feat of raw strength, and I think it deserves a check to make it happen. (Just for clarity, carrying Io would normally cut your speed in half, and climbing a ladder is also at 1/2 speed, so the above check is you pushing past your normal movement limitations to do a feat of heroic strength.)

Hearing the yelling from below Kassiopeia shouts in the direction of the Jester: "IT'S A TRAP!" (free action)
Chanting a short prayer to Karametra she creates an oversized cornocopia floating in the air in front of the merchant which swings at him rather angrily (Cast: Spiritual Weapon lv.2) (bonus action)
Attack: 15
Damage: 5

Taking a few steps to the side she gets ready to slam the hatch shut and lock/bar/secure it, once the last of their group has emerged from the lower deck. (ready an action)

Edit: (OOC dice roller messed up)

Quote from DragonDenn >>

Ritha give me an athletics check, to carry Io up the ladder and to the upper deck. This is a feat of raw strength, and I think it deserves a check to make it happen. (Just for clarity, carrying Io would normally cut your speed in half, and climbing a ladder is also at 1/2 speed, so the above check is you pushing past your normal movement limitations to do a feat of heroic strength.)

 Io would be very cooperative since he wants to get out of there as well. I know it's not Io's turn and thus can't really take any actions but would him being very cooperative with being dragged up the ladder work for giving Ritha advantage?

I will say Ritha has advantage on the athletics check, as Io aids in grabbing the ladder and such when possible. It is not like Ritha is just carrying dead weight after all. The DC is not all that high here either, do to Io helping out.

Ritha Athletics (with advantage): 15

Ritha managed an impressive feat of strength, lugging Io up the ladder and both flopping, prone, onto the deck above.

Kassiopeia creates a floating cornacorpia that then slams into the merchant, bashing him hard. Moving to the side of the hatch, she grips the door to the latch, prepared to slam it shut as soon as her companions are safely out of the hold.

As its reaction, The pirate first mate strikes at Ritha as they go up the ladder... Longsword. Melee Weapon Attack: 21 to hit, reach 5 ft., one target. Hit: 3 slashing damage. (add 7 if a crit.)

As its reaction the bandit near the ladder strikes at ritha as well, as they leave his reach... Light Crossbow. Ranged Weapon Attack: 16 to hit, range 80 ft./320 ft., one target. Hit: 7 piercing damage. (add 2 if a crit.)

The pirate first mate then strikes at Kanlos... (normal turn action. Move to d10) Longsword. Melee Weapon Attack: 15 to hit, reach 5 ft., one target. Hit: 7 slashing damage. (add 2 if a crit.)

Kanlos and Spyro are up. Not going to update the map just yet, will wait for Kanlos's action, as the lower battle might be over if he gets out of there before he can be totally cut off from the exit. Also, that last attack should not have had advantage on Kanlos, only use the first of the two attack rolls from that last post. As with Ritha, you will have attacks of opportunity against you as you go up the ladder, so be aware. The bandit can't actually do so again, as they already used their raction, and have not had a turn again yet. The first mate can though, as their reaction has reset with them having their normal action just now.

The only enemy above deck is the captain correct?

Ritha grits her teeth and grunts in pain as both the blade cuts deeply into her.  Still, somehow, she manages to make it up top, panting and hoping that Kanlos will follow them up swiftly so they can trap the bandits below and commandeer the pirate ship.

(Actually the bandit with the crossbow can't hit, you don't get attacks of opportunity with ranged weapons, even when you're in melee range and even if you have the crossbow expert feat.)

(Ok, bandit does not get the attack of opportunity with the crossbow. Also, yes just the one enemy on the top deck.)

"I knew it! Your corpse will be an offering to Thassa's the satyr would shout. Spyro would bound quickly towards the captain and pull the carved rod from his pocket. Pointing it towards the man he would quickly cast witch bolt while simultaneously moving to position himself behind anything that could provide some cover while allowing him to maintain his concentration on the enemy. 

Attack: 23 Damage: 3

"Thassa!" Ritha manages to groan weakly from her prone position on the deck.

Kanlos flinches back from the blow (still hits) and then pushes the blade further out of the way as it slices past and heads up the ladder, looking for a way to bolt it as Kassiopeia slams it shut.

Bonus action-disengage
Movement-up ladder
Action-try and bolt/cover door if possible

As Kanlos emerges from the hatch Kassiopeia slams it shut, drops her shield on top and kneels on the shield to put some extra weight on.

Using the bolt/bar to seal the cargo hold shut.