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  • Writer's pictureMark S. Cookman

Alternate Sailor Backgrounds for D&D 5e: The Jack Tar

For my own D&D 5e campaign, which is based mostly upon the high seas of various worlds, one background for a generic sailor just didn't work. On the coast, everyone sails. Because there are many different types of sailors and nautical personalities, I felt that there needed to be more variety than just one generic sailor so I created five additional nautical backgrounds to supplement the original sailor/pirate. They are merchant sailor/smuggler, marine, deep water sailor/explorer, jack tar, and fisherman/whaler. It is my plan to release one each day of this week. This is the third one. Here is where you can find the sailor/smuggler, here is where you can find the marine and here is where you can find the fisherman, in case you missed them. Finally, I hope you enjoy the jack tar.​

Jack Tar

You were born on the coast and the smell of the sea has always been in your nostrils; you can't imagine living anywhere else. You were brought up around hard-working men and women of the sea, but you've seen how some can make their own luck. Luck that brings a fortune 100 years of hard work could not. You have always looked for the quick fix, the fast coin, and the dream that is just over the horizon. At the same time, you have avoided long-term commitments, contracts, and duty-bound service to others in favor of the freedom to chase that illusive dream. Someday you'll catch it and then they'll all see.

You work as you are able at a variety of jobs around the port. You've been a temporary crewman, a harbor pilot, a nailer working in the shipyards, a long shoreman unloading freight onto the docks, a bouncer at the tavern, and a night time guard at the warehouses. You have sailed short term with a few independant crews, but the rigorous, never-ceasing duty of a merchant seaman or a navy sailor just isn't for you. You have had a variety of short careers over your life and you might stink of tar right now, but that's unimportant because some day you'll be the one everyone looks up to.

After choosing this background, you must work with the Dungeon Master to determine what kind of positions you have held. Roll randomly or choose 1d4+1 (2 - 5) previous jobs from the table below. The DM should also work out with you how you left your previous employers and whether or not they would hire you again.

Previous Jobs

d10 Previous Job

  1. You once worked as a night guard at a dockside warehouse. You weren't even working the night it got robbed by pirates, but you still lost the job.

  2. You worked as a sailor on a coastal merchant ship once that hit three different ports, each one only seperated by a week. You had a hot lover in all three. Pity that #2 was the bosun's sister. That kinda ruined the whole gig.

  3. You spent a year completely by yourself once, 3/4 of mile out on lighthouse island. They say that mermaids share a special bond with lighthouse keepers, but now you think they only tell people that to get them to sign up for the job.

  4. You worked as a cook in a dockside inn for a while, but that's nothing to write home about. It was 500 days of cooking and serving the same fishy slop to the same fishy customers.

  5. "I was working as a nailer in the shipyards when they built the Andromiche. I think she's got a double-reinforced hull with eight foot wide oaken. . .wait. . .did you say Andromida? Oh. Sorry, mate, I don't know. So many ships with so many names, plus I was the one hammered most of the time, if you know what I mean."

  6. "I was once the sole helmsman on the King's Ship, Interpid. I got called in as a harbor pilot to get her off the sandbar at the entrance to the channel. They ferried everyone else off the ship when they left me on it, but that's really beside the point I think."

  7. You spent three summers working for a cooper. Your job was to pitch the inside of some of the barrels he made. Every time you smell fresh pitch, you think of those long, hot, sticky summers, also most of your sense of smell is now gone.

  8. You worked for two years on the docks, loading and unloading cargo from the trade guild ships. It was miserable, back-breaking work. You hated absolutely everything about that job except the coins they paid you to do it.

  9. You spent two and a half years working in a waterfront bar. So you can say you've seen your share of fights, but mostly you just mopped up puke and washed glasses too stained to ever really be clean.

  10. You spent almost four years as an apprentice to a master carpenter. It sounds much more glamorous than it really was. Truth be told, you spent nearly four years cutting long boards into shorter boards before you realized how bored you had become.

Skill Proficiencies: Athletics and your choice of Insight, Intimidation or Persuation.

Tool Proficiencies: One artisan's tool set from a previous profession, Vehicles(water)

Equipment: A toolset from a former profession, a set of bone dice or a deck of cards, a set of common clothes, a leather flask of alcohol, and a belt pouch containing 10 gold.

Alternate Feature: Local Contacts

You are known to many in this port region because you once spent a few years here working various jobs for various folks. You know the basic "ins and outs" of the region and get to roll with advantage when searching for any particular resource to determine if and where it may be located or who might know. Additionally, you have one (plus a number equal to your charisma modifier, as long as that number is positive) contact(s). You must work with the Dungeon Master to determine the nature of your contact(s) and what benefits they might occasionally provide. Remember being well known around the region does not mean that you are well liked. Depending upon your history you may have more enemies than friends.

Local Contacts is an alternate feature that can be chosen instead of Ship's Passage (detailed on page 139 of the 5e PHB). Remember that a character may only have one background feature.

Suggested Characteristics

Please refer to the tables below to determine your personality trait, ideal, bond, and flaw.

Personality Traits

d8 Personality Trait

  1. I am a very amorous person. I have been with many partners already, but I am always looking for my next great love.

  2. I rarely have a plan for when things go wrong, because planning for things to go wrong is stupid. Besides, I'd rather just think on my feet.

  3. I work hard when I have to, but I'd just as soon let the other guys do the heavy lifting. I'm more of what you'd call the brains than those other guys.

  4. When I come into a new area, I'm greedy for information about forgotten ruins, abandoned manors, and hidden tombs. I collect treasure maps and legends like a dung heap collect flies.

  5. I sometimes get lost in my own thoughts and daydreams. When I do, I become completely oblivious to my surroundings.

  6. Sometimes I lie for absolutely no reason, just to watch the chaos insue.

  7. I'd rather sit back and plan out every possible aspect of an encounter before just leaping in. No one thinks well on their feet.

  8. I have a very bad reputation, but none of it's really my fault. My family is cursed by a powerful fiend, fey, or undead entity.


d6 Ideal

  1. Independence - I am free to make my own choices and follow my own paths. No one ties me down or forces me to do what I do not want. (Chaotic)

  2. Aspiration - I know that I will become a great success and that nothing that is going on right now can prevent that from happening in my future. (Any)

  3. Power - When I gain enough power, no one will be able to tell me what to do. (Evil)

  4. Community - We all must put aside our differences, pitch in, and work together if we hope to be as successful as we can be. (Lawful)

  5. People - I don't believe in religions, philosophies, or governments; I believe in people. (Neutral)

  6. Respect - People deserve to be treated with dignity and respect no matter who they are. (Good)


d6 Bond

  1. Somewhere out there I'm sure that I have sons and daughters who don't know me. I have to make the world a better place for myself, and for them.

  2. I am actually descended from a noble line. Once my nobility has been officially recognized, I will have my vengence upon those who displaced me.

  3. I have numerous back debts to people in the community, but I have a reputation for paying people back with more than was originally loaned.

  4. Someday I will become more powerful and influential than even I ever dreamed, but I will never forget where I came from. I will return home some day to reward the people and make the place greater than anywhere else in the world.

  5. I will always remember my first ship and my first captain. He changed my life with his words.

  6. Ruthless pirates raided my town by night, killed many of my family members and friends in their beds, plundered the place, set it to the torch, and sailed away before sunrise. I swear by all that is holy and unholy that I will track them down and have my revenge.


d6 Flaw

  1. I'm a sucker for a pretty face and smooth words.

  2. I always think that I can drink more than anyone else in the tavern. I am usually wrong.

  3. I often jump to the worst conclusions about people; I think that people are out to get me.

  4. I won't follow orders that I believe are wrong and I will make a scene about it.

  5. I can't keep a secret to save my own life, or anyone elses for that matter.

  6. Violence is too often my answer to any challenge. This behavior has landed me in trouble more than once.

#dnd #DnD #5e #pirate #rpg #dmadvice

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