Spoiler: OOC: Battlefield Info
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Will be trying a mapless approach for this one.
Approximate ranges between areas are given. Those within a given area are all within movement range of one another unless they seek a specific position somewhere using greater movement speed. Characters may engage other characters in the same area in melee unless unable for some reason, entering threat range using their movement.

Enemies taking cover will lose cover when engaged in melee by a creature, or by a threatening spell such as Create Bonfire or Flaming Sphere smoking them out.

A ship without a manned navigation and/or propulsion is unable to move effectively. Siege attacks and spells used against a stationary ship hit/fail Dex saves automatically. Characters manning navigation can wield weapons or cast spells with one hand without leaving their position unmanned.

We'll feel out more as we go.

East Cliff: Creatures without a Climb speed treat the ground as Difficult Terrain / ~30 feet from Naval Battle, ~100 feet up / ~180 feet from West Cliff
Sarith: Exposed Weakness (1d4), Wither 3
Nilvae, Engaged by Giant Spiders A&B
Mr. Spide, Engaged by Giant Spiders A&B
Enemies
Drow Agent: Near Death
Drow Scout A: Unharmed, Half Cover
Drow Crossbowman A: Dying, 1 Success
Drow Arcane Archer A: Scratched, Half Cover
Giant Spider A: Unharmed, Engaging Spide and Nilvae
Giant Spider B: Unharmed, Engaging Spide and Nilvae

West Cliff: ~180 feet from Naval Battle, ~80 feet up / ~180 feet from East Cliff
Galdar: Riding Charlotte
Charlotte: Climbing on Cliffside
Allies
Topsy: Damaged, Riding Charlotte
Enemies
Drow Scout B: Dead
Drow Crossbowman B: Bloodied, Falling from Cliffside
Drow House-Mage of Mizzrym: Unharmed, Concentrating on Fly, 60 feet off the cliffside
Giant Spider C: Dead
Giant Spider D: Dead

The Black Manta (Damaged, Burning 1): ~100 feet down, ~60 feet away from East Cliff / ~80 feet down, ~200 feet away from West Cliff
Faedryl: Concentrating on Create Bonfire under Drow Sailor B's Harpoon Gun
Elara: Bloodied, Twilight Sanctuary (1d6+5)
Borthan: Manning Steering Comms (decides if the ship moves closer or further away, Sailing tool check used for ship's Dex saves)
Derendil
Ront: Tower Shield Half-Cover towards Drow Ships, Dawnbringer Shining
Turvy: Badly Wounded, Unconscious (Drow Poison)
Allies
Kuo-toa Sailor A: Dying, 2 Failed, 1 Succeeded
Kuo-toa Sailor B: Unharmed, Belowdecks, manning Oars
Kuo-toa Sailor C: Unharmed, Belowdecks, manning Oars
Kuo-toa Sailor D: Unharmed, Belowdecks, manning Oars
Kuo-toa Sailor E: Dying, 2 Succeeded, 1 Failed
Kuo-toa Marauder B: Dying, 2 Failed
Dr. Donk: Unharmed, Belowdecks, manning Oars
Stool: Unharmed
Enemies
Drow Venomancer A: Dying, Poisoned Weapon
Drow Venomancer B: Dying, Poisoned Weapon
Giant Spider F: Dead
Drow Hexer A: Dead
Drow Hexer B: Dead
Mini Retriever A: Dead
Mini Retriever B: Dead

The Iron Eel (Undamaged): Surfaced alongside DSHS 1
Allies
Blurg: Unharmed
Y: Unharmed

Dark Pirates' Duergar Sloop (Undamaged):
Allies
Orog Wilder: Near Dead, Vision 5 ft. until Arcane Archer turn, manning Wheel, Engaged by Venomancer D
Orc Deckhand A: Near Dead, manning Cannon, Cannon needs loading action, Engaged by Venomancer C and Hexer D&E
Orc Deckhand B: Dying, 1 Failed, at Cannon, Cannon needs loading action, Engaged by Venomancer C
Orog Arbalest: Unharmed, Belowdecks, positioned in Bunker, Engaged by Hexer C
Orog Stonehorn: Unharmed, Belowdecks, manning Crystal Engine
Enemies
Drow Venomancer C: Unharmed, Engaging Orc Deckhand A and B
Drow Venomancer D: Unharmed, Engaging Orog Wilder
Drow Hexer C: Unharmed, Poisoned Weapon, in Bunker, Engaging Orog Arbalest
Drow Hexer D: Unharmed, Engaging Orc Deckhand A
Drow Hexer E: Unharmed, Engaging Orc Deckhand A

Drow Slave-Hunter Ship 1 (Enchanted Hull, Damaged, Slowed (Siege attacks have Advantage)): Crow's Nest ~20 feet up
Allies
Kuo-toa Marauder A: Lightly Damaged, 2 Bleed, Belowdeck, Recklessly Attacked
???
Jorlan (scarred male drow from Velkynvelve): Bloodied
Enemies
Ilvara Mizzrym, Priestess-Commander of Velkynvelve: Damaged
Shoor (Ilvara's lover): Damaged
Asha (Ilvara's junior priestess): Dying, 2 Succeeded
Drow Elite A: Scratched, 2 Bleed, in the water
Drow Elite B: Scratched, 2 Bleed, in the water
Drow Arcane Archer B: Scratched, 2 Bleed, in water
Drow Wizard: Dead
Drow Crossbowman C: Dying, 1 Success, Guiding Bolted, in Crow's Nest
Drow Crossbowman D: Unharmed in Crow's Nest
Drow Sailor A: Unharmed, manning Wheel
Drow Sailor B: Bloodied
Drow Sailor C: Damaged, 2 Bleed, in the water
Harpoon Gun B: Harpoon attached to Black Manta

Drow Slave-Hunter Ship 2 (Rudderless, Sinking 2) Crow's Nest ~20 feet up
ALADIN: Belowdeck
Enemies
Drow Crossbowman E: Unharmed, in Crow's Nest
Drow Crossbowman F: Unharmed in Crow's Nest
Drow Sailor D: Unharmed, manning Wheel
Drow Sailor E: Unharmed, manning Harpoon Gun, Harpoon attached to Pirate Ship
Drow Sailor F: Unharmed, manning Harpoon Gun, Harpoon attached to Pirate Ship


Spoiler: Initiative
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With Timing, the naval battle will begin on round 2. Characters on the Manta can currently see the flanking battles, but the enemies above have 3/4 cover from the angle. Characters above have a vantage to fire on characters on the drow ships.

Jorlan - n20

Drow Agent (Legendary Action) - 23
Ilvara (Legendary Action) - 22
Drow Agent - 18

Orog Arbalest - 17

Ilvara Mizzrym, Velkynvelve Priestess-Commander - 16

Orog Wilder - 15
Orc Deckhands - 15
Kuo-toa Marauders - 15
Elara/Turvy - 14

Drow Venomancers - 14
Drow Crossbowmen - 14
Drow Sailors - 14

<inhale> Faedryl/Sarith/Nilvae/Spide/Donk/Galdar/Charlotte - 13

Shoor - 12
Drow Scouts - 12
Giant Spiders - 12
Drow House-Mage (Legendary Action) - 11
Drow Elites - 11

Kuo-toa Sailors - 10

Asha - 10
Drow Arcane Archers - 9
Drow Hexers & Mini Retrievers - 9

The Iron Eel - 8
Borthan/Derendil - 8

Drow House-Mage - 8

ALADIN/Ront - 6
Topsy - 6
Orog Stonehorn - 5
Stool - 4

Borthan and Derendil are up! ALADIN and Ront may also act.


East Cliff

Light of healing soothes Sarith's pain, forcing its way past the cursed flesh as strands of crawling growths struggle to close the wound alone. His weapon is as true as hers', however, and his bolt finds its mark in the agent's shoulder as she tries to fall back into cover. The trail of blood left behind her suggests he hit something dire.

Popping between cover for long enough to get a shot off, the agile scout strikes Nilvae with an arrow. The opening allows another spider bite to land upon her, and Spides is unable to evade the same fate this time as one of his lesser, Lolth-touched kin sinks her violet fangs in.

Hounded by Sarith's cursed spirits, the arcane archer draws another arrow and fires. This one is not ensorcelled, and Sarith's cover deflects it.

Spoiler: Combat Log
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Sarith sneak attacks Drow Agent for 21 damage, Bloodying her and nearly enough to KO. Whispers deals 2 more damage to Arcane Archer A.
Sarith regenerates 3 hit points from his crawling flesh, but Withering negates it.
Sarith is healed for 5 and 10 after Withering, by Nilvae and Spide.

Scout A shoots Nilvae for an 11 damage sneak attack.
Giant Spider A bites Nilvae for 4 damage, and 3 poison after a successful save.
Giant Spider B bites Spide for 10 damage, and 6 poison after a successful save.
Arcane Archer A shoots at Sarith, but misses.


West Cliff

With the spiders cut down, Galdar guides Charlotte forward. Palm stretched in front of him, he conjures a flood of thunderous sound that blasts the remaining drow solder from the cliffside, sending him into a deadly plummet towards the inky black water below. His steeder steps down the cliffside, now perched with her riders seated horizontally on the steeder saddle.

Turning back to look at the thunderous sound, the drow mage scowls and reaches out a hand. A thorny vine stretches out over the long gap between them and wraps itself around Charlotte's leg, stinging it with tiny blades as he tries to yank her towards him and break her grip on the cliffside. She holds.

Spoiler: Combat Log
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Galdar casts Thunderwave, blasting Crossbowman B off the ledge and dealing 21 damage.
Charlotte moves over the edge onto the side of the cliff.

Drow House-Mage uses his Legendary Action to hit Charlotte with a range-extended Thorn Whip, dealing 7 damage and yanking her towards him. Since he is not directly away from the wall, she passes a Dex save to avoid losing her grip.


Naval Battle

With a telekinetic yank, Faedryl pulls one of the drow sailors over the railing. He plummets into the icy water, quickly chewed on by fish. A cursed ringing hounds Shoor's ears, and he looks pale as her cantrip sinks into him, weakening him. He, however, is more concerned with coming to the defense of his lady.

Drawing his shortsword, Shoor joins the fight against Jorlan on the opposing deck, but his weapon is parried. Jorlan is maimed, but no less swift.

From the second ship, two drow in the longcoats of the warrior elite take aim with their hand crossbows. One bolt strikes Borthan, and the second hits Turvy - who passes out on the deck of the ship. Their shots fired, the two of them leap from the sinking ship to avoid being pulled down by its suction, swimming towards their sister vessel.

From under the water, a long metallic shape rises alongside Ilvara's ship. The crew, those who notice it, give it confused looks - and fearful ones from those in the water. The party knows it to be the Iron Eel, hopefully surfacing to lend more direct aid.


The pirates are not doing well. The surrounded deckhand is nearly toppled by the blows coming from all sides, and the one on the floor is on fire.

Spoiler: Combat Log
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Faedryl pulls Drow Sailor into the water, where he takes 5 damage and 2 Bleed from carnivorous minnows.
Faedryl casts Toll the Dead on Shoor, dealing 7 damage.

Shoor attacks Jorlan twice with a shortsword, but misses both.
Drow Elite A shoots Borthan for 10 damage.
Drow Elite B shoots Turvy for 10 damage, and he fails a save against Drow Poison, falling unconscious.
The two elites jump ship, taking 2 and 5 damage respectively and 2 Bleed from the fish.
Arcane Archer B Dashes to get down from the crow's nest, and jumps into the water after them, taking 3 damage and 2 Bleed.

Hexer C strikes Orog Arbalest for 24 critical damage and Bloodies, but they resist the drow poison.
Hexer D strikes Orc Deckhand A for 10 damage, Orc Deckhand B takes 10 from green-flame and is now dying.
Hexer E strikes Orc Deckhand A for 4 damage, Orc Deckhand B takes a failed death save from green-flame.


Underwater

Spoiler: Combat Log
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The Iron Eel attempts to grapple Ilvara's ship again, but the enchanted hull resists the grip of its teeth.
The Society members abandon the attempt and begin to surface.