The Triolan corsairs are renowned throughout Midgard for their flamboyant ferocity and near monopoly on organized shipping and piracy throughout the (northern) Middle Sea. But the sea lanes and merchant armadas are not the only means to move goods and services to and from the rich trade centers of the great peninsula. Eager merchants still foolishly brave back roads and “shortcuts” to hurry their goods to Tolmezo, Melana, and Peltzheim. Likewise, the coastal roads to Raguza or west into Trombei are rich with petty nobles and their slackjawed coachmen, careless smugglers, and the occasional tax collector caught out after dark.
You, however, were no roadside robber or woodland brigand. You counted yourself among the storied (and the somewhat storied) Triolan highwaymen, many of whom are still recounted in tavern songs and bawdy, roadhouse limericks.
The “title” of highwayman is most often bestowed by the local populace or by regular association with a reputable highwayman. It denotes an individual (frequently a bastard of the gentry or a disgraced, rebellious, or disillusioned aristocrat) who has established a reputation (or a secret identity) for flair, finesse, and even fashion while exhibiting abhorrence for violence and bloodshed.
You are courteous, polite, and charming, and even in the face of death, your etiquette is impeccable. As a highwayman, you championed the liberties (resentments) of the peasantry, targeting only the rich and powerful: members of the merchant monopolies, corrupt officials, and decadent nobility, some of whom may have been peers or associates of yours at one time. Most highwaymen are rumored to support local causes and reforms or somehow give back to the region or the less privileged.
Triolan Highwayman (Variant Folk Hero)
Skill Proficiencies: Deception and choose 1 from Acrobatics, Athletics, Perception or Persuasion
Languages: Southern and Trade Tongues
Tool Proficiencies: A musical instrument of your choice, a gaming set of your choice, vehicle (land)
Equipment: A token or memento of a happier past, a set of traveler’s clothes, a (stolen?) riding horse (with saddle and tack), a leather belt-pouch containing 3 gp
Feature: Flattery, Footwork, and Flourish
With swirling cloak, flashing blade, and rapier wit, you taunt, tease, and vex your opponent. Whenever you take the attack action, wielding a one-handed, versatile weapon you are proficient with, all allies within 15 ft. who can see, hear, and understand your antics may add 1d4 to any attack rolls or saving throws that turn. This feature may be used once between long rests. Additionally, you are always considered proficient in Animal Handling when dealing with animals of an equine nature.
For the admiral’s tour of that scandalous and swashbuckling city-state Triolo (and their neighbors, peoples, powers, and politics), be sure to check out the Midgard Campaign Setting from Kobold Press. Or