You sailed the seas as a freebooter, part of a pirate crew. You should come up with a name for your former ship and its captain, as well as its hunting ground and the type of ships you preyed on. Did you sail under the flag of a bloodthirsty captain, raiding coastal communities and putting everyone to the sword? Or were you part of a group of former slaves turned pirates, who battle to end the vile slave trade? Whatever ship you sailed on, you feel at home on board a seafaring vessel, and you have difficulty adjusting to long periods on dry land.

Skill Proficiencies: Athletics, Survival

Tool Proficiencies: Navigator’s tools, vehicles (water)

Equipment: A pirate flag from your ship, several tattoos, 50 feet of rope, a set of traveler’s clothes, and a belt pouch containing 10 gp

Feature: A Friendly Face in Every Port

Your reputation precedes you. Whenever you visit a port city, you can always find someone who knows of (or has sailed on) your former ship and is familiar with its captain and crew. They are willing to provide you and your traveling companions with a roof over your head, a bed for the night, and a decent meal. If you have a reputation for cruelty and savagery, your host is probably afraid of you and will be keen for you to leave as soon as possible. Otherwise, you receive a warm welcome, and your host keeps your presence a secret, if needed. They may also provide you with useful information about recent goings-on in the city, including which ships have been in and out of port.

Suggested Characteristics

Freebooters are a boisterous lot, but their personalities include freedom-loving mavericks and mindless thugs. Nonetheless, sailing a ship requires discipline, and freebooters tend to be reliable and aware of their role on board, even if they do their own thing once fighting breaks out. Most still yearn for the sea, and some feel shame or regret for past deeds.

d8 Personality Trait
1 I’m happiest when I’m on a gently rocking vessel, staring at the distant horizon.
2 Every time we hoisted the mainsail and raised the pirate flag, I felt butterflies in my stomach.
3 I have lovers in a dozen different ports. Most of them don’t know about the others.
4 Being a pirate has taught me more swear words and bawdy jokes than I ever knew existed. I like to try them out when I meet new people.
5 One day I hope to have enough gold to fill a tub so I can bathe in it.
6 There’s nothing I enjoy more than a good scrap—the bloodier, the better.
7 When a storm is blowing and the rain is lashing the deck, I’ll be out there getting drenched. It makes me feel so alive!
8 Nothing makes me more annoyed than a badly tied knot.
d6 Ideal
1 Freedom. No one tells me what to do or where to go. Apart from the captain. (Chaotic)
2 Greed. I’m only in it for the booty. I’ll gladly stab anyone stupid enough to stand in my way. (Evil)
3 Comradery. My former shipmates are my family. I’ll do anything for them. (Neutral)
4 Greater Good. No man has the right to enslave another, or to profit from slavery. (Good)
5 Code. I may be on dry land now, but I still stick to the Freebooter’s Code. (Lawful)
6 Aspiration. One day I’ll return to the sea as the captain of my own ship. (Any)
d6 Bond
1 Anti-slavery pirates rescued me from a slave ship. I owe them my life.
2 I still feel a deep attachment to my ship. Some nights I dream her figurehead is talking to me.
3 I was the ship’s captain until the crew mutinied and threw me overboard to feed the sharks. I swam to a small island and survived. Vengeance will be mine!
4 Years ago, when my city was attacked, I fled the city on a small fleet bound for a neighboring city. I arrived back in the ruined city a few weeks ago on the same ship and can remember nothing of the voyage.
5 I fell asleep when I was supposed to be on watch, allowing our ship to be taken by surprise. I still have nightmares about my shipmates who died in the fighting.
6 One of my shipmates was captured and sold into slavery. I need to rescue them.
d6 Flaw
1 I’m terrified by the desert. Not enough water, far too much sand.
2 I drink too much and end up starting barroom brawls.
3 I killed one of my shipmates and took his share of the loot.
4 I take unnecessary risks and often put my friends in danger.
5 I sold captives taken at sea to traders.
6 Most of the time, I find it impossible to tell the truth.
Section 15: Copyright Notice

Tome of Heroes ©2022 Open Design LLC; Authors: Celeste Conowitch, Jeff Lee, Sarah Madsen, Ben McFarland, Kelly Pawlik, Brian Suskind

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