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: Wither 3, Engaged by Spider B
Nilvae: Dying, 2 Failed
Mr. Spide: Banished
Enemies
Drow Agent Xalith: Dying, 1 Success
Drow Crossbowman A: Dying, 1 Success, 2 Fail
Giant Spider A: Dead
Giant Spider B: Unharmed, Engaging Sarith
Surrendered
Drow House-Mage Ulryn of Mizzrym: Unharmed, Concentrating on Fly, Surrendered
Drow Scout A: Unharmed, Half Cover, Surrendered
Drow Arcane Archer A: Scratched, Half Cover, Surrendered

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: Dead
Giant Spider C: Dead
Giant Spider D: Dead

The Black Manta (Damaged): ~100 feet down, ~60 feet away from East Cliff / ~80 feet down, ~180 feet away from West Cliff / ~5 feet from Pirate Ship
Faedryl: Concentrating on Create Bonfire under Drow Sailor B's Harpoon Gun
Elara: Bloodied, Twilight Sanctuary (1d6+5)
Turvy: Badly Wounded
Allies
Kuo-toa Sailor A: Unconscious, Stable
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: Unconscious, Stable
Kuo-toa Marauder B: Dead
Dr. Donk: Unharmed, Belowdecks, manning Oars
Enemies
Drow Venomancer A: Dying, 2 Failed, 1 Succeeded, Poisoned Weapon
Drow Venomancer B: Dying, 1 Succeeded, 2 Failed, 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): Underwater, alongside DSHS 2
Allies
Blurg: Unharmed, Manning Steering

Dark Pirates' Duergar Sloop (Undamaged): Stalled Out (no power to engines) / ~5 feet from Black Manta
Allies
Borthan: Engaging Hexer E and Mini Retriever D
Derendil: Engaging Hexer E and Mini Retriever D
Stool: Scratched, Concentrating (Healing Spirit)
Orog Wilder: Near Dead, Vision 5 ft. until Arcane Archer turn, manning Wheel, Engaged by Venomancer C
Orc Deckhand A: Dying, Engaged by Hexer E, sharing space with Healing Spirit (heal 1d6 at turn start)
Orc Deckhand B: Dead
Orog Arbalest: Bloodied, Belowdecks, positioned in Bunker, Engaged by Hexer C
Orog Stonehorn: Unharmed
Enemies
Drow Venomancer C: Dying, 2 Failed, 2 Bleed
Drow Venomancer D: Dying, 2 Succeeded
Drow Hexer C: Damaged, in Bunker, Engaging Orog Arbalest
Drow Hexer D: Dead
Drow Hexer E: Scratched, Engaging Orc Deckhand A, Borthan and Derendil
Mini Retriever D: Unharmed, Engaging Borthan and Derendil

Drow Slave-Hunter Ship 1 (Enchanted Hull, Damaged, Slowed (Siege attacks have Advantage)): Crow's Nest ~20 feet up
Allies
Ront:
Dawnbringer: Caught on a railing, Dawnbringer Shining (Disadvantage to Drow attacks on board)
Kuo-toa Marauder A: Lightly Damaged, 2 Bleed, Belowdeck, Recklessly Attacked
Y: Unharmed
???
Jorlan (scarred male drow from Velkynvelve): Dying, 1 Failed
Enemies
Ilvara Mizzrym, Priestess-Commander of Velkynvelve: Dying, 1 Failure, 1 Success
Shoor (Ilvara's lover): Dying
Asha (Ilvara's junior priestess): Dying, 2 Succeeded, 2 Failed
Drow Elite A: Damaged, 6 Bleed, in the water
Drow Elite B: Damaged, 8 Bleed, in the water
Drow Arcane Archer B: Near Death, 6 Bleed, in water
Drow Wizard: Dead
Drow Crossbowman C: Dying, 2 Success, 1 Fail, in Crow's Nest
Drow Crossbowman D: Bloodied, Sawbladed
Drow Sailor A: Unharmed, manning Wheel
Drow Sailor B: Bloodied
Drow Sailor C: Bloodied, 2 Bleed
Drow Sailor D: Bloodied, 2 Bleed, in water
Drow Sailor E: Bloodied, 4 Bleed, in water

Drow Slave-Hunter Ship 2 (Rudderless, Sunken) Sunken
ALADIN: Belowdeck, Sunken
Enemies
Drow Crossbowman E: Scratched, 2 Bleed, Sunken (removed from combat)
Drow Crossbowman F: Scratched, 2 Bleed, Sunken (removed from combat)
Drow Sailor F: Damaged, 2 Bleed, Grappled by Slave Mob A, Sunken (removed from combat)
Drow Slave Mob A: Damaged, 2 Bleed, Grappling Drow Sailor F, Sunken (removed from combat)
Drow Slave Mob B: Damaged, 2 Bleed, chained belowdeck, Sunken (removed from combat)


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 Xalith (Legendary Action) - 23
Ilvara (Legendary Action) - 22
Drow Agent Xalith - 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 Ulryn (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 Ulryn - 8

ALADIN/Ront - 6
Topsy - 6
Orog Stonehorn - 5
Stool - 4
Drow Slave Mobs - 0

Stool is up!


Naval Battle

A quick vault over the railings brings Borthan onto the pirate ship as the rowers stop beside it. No matter - the enemy ship seems to be retreating. With a mark guiding his hand, a pair of two axe strokes brings down one of the large, bare-chested drow hexers. The scarified tattoos across his back glow and erupt into another bloody, metal arachnid. Derendil follows him over, angling his trident at the last hexer on the deck, but the weapon is caught on their foe's morningstar and turned away.

Leaping from the railing of the Black Manta, Ront activates the reeling function of his gauntlet. Much like the technique used by the drow boarders to leap onto their ship with their silk tethers, he hurls himself across the water. Landing firmly on the deck and letting the chain go slack again, he rushes the feebly standing Shoor. In spite of fading consciousness, the drow twists and parries the first gut punch with his gleaming shortsword, squinting against the glare of sunlight ringing Ront's looming eclipse.

The backhand that follows he doesn't have strength left to resist, and it sends him sprawling to the ground.

Spoiler: Combat Log
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Borthan hops onto the pirate ship and marks Hexer D. First hit deals 14 damage and the second deals 12, enough to finish him off. Mini Retriever D bursts from the corpse. Hunter's Mark is reassignable with a bonus action.
Derendil hops onto the pirate ship and barely misses Hexer E.
Ront successfully leaps to Ilvara's ship.
Ront's first swing is deflected by a Parry reaction, but he can't deflect the second which KO's him.


Underwater

Persistently, ALADIN works at the look upon the wall and is able to pull it loose with his multitool. The chained slaves begin trying to claw their way up from the sinking ship, even as the fish that flooded in with them gnaw at flesh and leave trails of red in the water.

Spoiler: Combat Log
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ALADIN frees Slave Mob B.