Sky Sailor
You served for years aboard a skyship, living with open air beneath your feet and the endless horizon ahead. You’ve flown through aether storms, battled sky-born creatures, and faced enemies determined to send your vessel plunging into the clouds below. Though the sky still calls to you, your life has taken a new course.
Work with your Dungeon Master to determine the nature of the skyship you served on. Was it a merchant vessel hauling cargo between floating ports, a military airship enforcing a nation’s will, an exploration craft charting unknown skies, or a sky-pirate ship living by speed and plunder? How well known was the ship—respected, feared, or quietly infamous? Is it still flying, or was it lost to disaster, betrayal, or war?
Decide what role you filled aboard the ship. Were you a deckhand, navigator, engineer, cook, officer, or captain? Who commanded the vessel, and who served as second-in-command?
Finally, consider how your service ended. Did you leave on good terms, seeking a different life? Were you forced out by tragedy or conflict? Or are you on the run, with former crewmates—or enemies—still watching the skies for you?
- Skill Proficiencies: Athletics, Perception
- Tool Proficiencies: Navigator’s tools, vehicles (Sky)
- Equipment:
Navigator's Tools, 50 feet of silk rope, a sky-charm (such as a shard of lift-crystal or a stamped docking token), a pair of reinforced sky-gloves (worn with your common clothes), a set of common clothes, and a pouch containing 10 gp.
When you need to, you can secure free passage on a ship for yourself and your adventuring companions. You might sail on the ship you served on, or another ship you have good relations with (perhaps one captained by a former crewmate). Because you’re calling in a favor, you can’t be certain of a schedule or route that will meet your every need. Your Dungeon Master will determine how long it takes to get where you need to go. In return for your free passage, you and your companions are expected to assist the crew during the voyage.
Suggested Characteristics
Sailors can be a rough lot, but the responsibilities of life on a ship make them generally reliable as well. Life aboard a ship shapes their outlook and forms their most important attachments.
| d8 | Personality Trait |
|---|---|
| 1 | My crew knows they can rely on me when the winds turn bad. |
| 2 | I work hard during a run so I can spend freely at the next skyport. |
| 3 | I love docking in new ports and trading stories with whoever will listen. |
| 4 | I exaggerate my tales of storms and sky-beasts—only a little. |
| 5 | A tense standoff on a docking platform doesn’t scare me. It excites me. |
| 6 | I never refuse a wager, especially about wind speed or navigation. |
| 7 | My language is as rough as a broken hull plate. |
| 8 | I prefer careful planning—but I’m not above letting someone else take the risk first. |
| d6 | Ideal |
|---|---|
| 1 | Respect. The thing that keeps a ship together is mutual respect between captain and crew. (Good) |
| 2 | Fairness. We all do the work, so we all share in the rewards. (Lawful) |
| 3 | Freedom. The open sky belongs to no king or council. (Chaotic) |
| 4 | Dominance. The skies reward strength; the weak fall. (Evil) |
| 5 | People. I’m committed to my crewmates, not to ideals. (Neutral) |
| 6 | Ambition. One day I’ll command my own vessel and choose my own course. (Any) |
| d6 | Bond |
|---|---|
| 1 | I’m loyal to my captain first, everything else second. |
| 2 | The ship is most important—crewmates and captains come and go. |
| 3 | I’ll never forget my first time leaving the ground behind. |
| 4 | There’s someone waiting for me in a skyport who nearly made me stay. |
| 5 | I was cheated out of my fair share of the profits, and I want to get my due. |
| 6 | Ruthless pirates murdered my captain and crewmates, plundered our ship, and left me to die. Vengeance will be mine. |
| d6 | Flaw |
|---|---|
| 1 | I follow orders, even if I think they’re wrong. |
| 2 | I’ll say anything to avoid having to do extra work. |
| 3 | Once someone questions my courage, I never back down no matter how dangerous the situation. |
| 4 | Once I start drinking, it’s hard for me to stop. |
| 5 | I can’t help but pocket loose coins and other trinkets I come across. |
| 6 | My pride will probably lead to my destruction. |
You served aboard a skyship that lived outside the law. Whether you called yourselves privateers, free traders, or something harsher, you survived by speed, nerve, and reputation. You raided merchant vessels, smuggled forbidden cargo, and vanished into cloudbanks before authorities could respond. Your ship’s name carried weight in dockyards—sometimes fear, sometimes admiration.
Consider what still follows you. A bounty? A rival crew? A former shipmate who wants revenge—or reunion?
If your character has a Sky sailor background, you may select this background feature instead of Ship’s Passage.
No matter where you go, people are afraid of you due to your reputation. When you are in a settlement, you can get away with minor criminal offenses, such as refusing to pay for food at a tavern or breaking down doors at a local shop, since most people will not report your activity to the authorities.
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