It would be ridiculous to try and out-do what Sean K. Reynolds has already brilliantly done for D&D 3.5 in The New Argonauts so at the start of every one of these posts I’m going to 1) thank him for making that supplement (thank you Sean!) and 2) tell you to go download it (it’s free–give it 5 stars because damn). This blog series is not intended to be a reproduction of that product, only a conversion update. Go get it.

Post 1: What You Need To Play

Master Page for D&D 5E Ancient Greece/Monster List

Scylla

Huge monstrosity, neutral
Armor Class 14 (natural armor)
Hit Points 46 (4d12+20)
Speed 20 ft., swim 40 ft.

Saving Throws Dex +5, Wis +3
Skills Athletics +7, Perception +6, Stealth +5
Damage Resistances bludgeoning, piercing, and slashing from nonmagical weapons
Senses darkvision 60 ft., passive Perception 16
Languages Common
Challenge 5 (1,800 XP)

Ageless. Scylla cannot suffer from frailty of old age, die from old age, or be aged magically.
Pounce. If Scylla moves at least 20 feet straight toward a creature and then hits it with a bite attack on the same turn, that target must succeed on a DC 15 Strength saving throw or be knocked prone. If the target is prone, scylla can make one bite attack against it as a bonus action.

ACTIONS
Multiattack. Scylla attacks seven times–once with her snake-tail and six times with her bite.
Bite. Melee Weapon Attack: +7 to hit, reach 10 ft., one target. Hit: 7 (1d6+4) piercing damage and if the target is a creature it is grappled (escape DC 15).
Snake-Tail. Melee Weapon Attack: +4 to hit, reach 15 ft., one target. Hit: 5 (1d6+2) piercing damage plus 4 (1d8) poison damage.

REACTIONS
Dog Heads. When Scylla uses her reaction to make an opportunity attack, she is able to take up to 5 more opportunity attacks before the start of her next turn. She can still only make one opportunity attack for each time a creature provokes.

The creature Scylla was once a beautiful human woman, daughter of a rivergod. She was loved by a man named Glaucon, who spurned Circe’s affections to pursue Scylla. In revenge, Circe poisoned the waters of Scylla’s favorite bathing pool with foul magic, and when Scylla went to bathe herself, the submerged portion of her body transformed into six barking dogs and a monstrous snake tail. Thereafter she lived in a seaside cave, living on fish, dolphins, and whatever sailors she managed to snatch from passing ships.

Scylla cares little for fighting and only attacks because she is hungry. She prefers to grapple one or more creatures with her improved grab ability, then retreat. If she fails to grab anyone with her first a􀄴acks, she tries again, and if those fail she retreats to wait for easier prey.

An Intelligence (History) check reveals the following information: 9—Scylla is a horrible female monster with six dogs and a snake tail instead of a lower body. She devours sailors whose ships come to close to her cave. 14—Scylla used to be human but was transformed by a jealous sorceress. When she attacks a ship, each of her six dog heads snatches a sailor, which she drags back to her lair to devour.