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

Charon

Medium monstrosity, lawful evil
Armor Class 18 (natural armor)
Hit Points 33 (6d8+6)
Speed 30 ft., fly 30 ft.

Saving Throws Wis +4, Cha +3
Skills Acrobatics +6, Insight +4, Intimidation +3, Perception +4, Religion +2, Stealth +6
Damage Resistances cold, fire, necrotic, radiant
Condition Immunities frightened
Senses darkvision 200 ft., passive Perception 14
Languages Common
Challenge 4 (1,100 XP)

Ageless. Charon cannot suffer from frailty of old age, die from old age, or be aged magically.
Magic Resistance. Charon has advantage on saving throws against spells and other magical effects.
Regeneration. Charon regains 5 hit points at the start of his turn. He dies only if he starts his turn with 0 hit points.
Unsinkable. While he remains within it, Charon has absolute control over his boat’s direction and speed, and it cannot sink while he is steering it. He cannot be removed from the boat against his will or made to leave it in any way.

ACTIONS
Quarterstaff. Melee Weapon Attack: +5 to hit, reach 5 ft., one target. Hit: 7 (1d8+3) bludgeoning damage. If the target is a creature, it must succeed on a DC 13 Strength saving throw or be pushed up to 10 feet away.

Charon is the ferryman of the dead, carrying spirits across the Styx if they were buried or cremated with a coin in their mouth, leaving them to wander the banks forever if they don’t. He appears an ugly older man with a grim face, conical hat, crooked nose, and a beard, though some see him as a winged fiend with snakes for hair (as a demon of the underworld, both may be his true form).

Charon prefers to deal with violent passengers by pushing them into the Styx. If frustrated in his attempts to push opponents into the river, he flies away with his pole, leaving his passengers to drift helplessly until they land on one bank or the other (randomly, 1d6 hours later).

An Intelligence (History) check reveals the following information: 10—Charon is the ferryman who takes souls across the Styx to the underworld. He won’t carry anyone unless they pay the toll of one coin. 15—Charon has ferried heroes across the Styx in the past, and charged them a coin for passage in each direction.