Sailor Background 5e – Don’t Overlook These Features!

© Wizards of the Coast

The sea rages with the fury of a god. A half-orc sailor struggles to keep his small ship from being torn asunder by the crashing waves and howling winds.

His companion—a human wizard—waits in the ship’s tiny cabin, frozen with terror. With his friend’s life on the line, the sailor carefully ties a bowline knot and remembers the words of his father: “Always check your knot twice, son.”

With the sailor background, your character will be a master of the high seas. Not only will you know how to sail a ship, but you’ll have the salty swagger of a veteran sailor. 

It’ll be up to you to decide how you learned this trade. Maybe you were employed on a merchant’s ship, or were raised by pirates. Either way, you’ll know how to use a compass and fight sharks.

Sailor Summary

Skill Proficiencies: Athletics, Perception

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

Languages: None

Equipment: A belaying pin (club), 50 feet of silk rope, a lucky charm such as a rabbit foot or a small stone with a hole in the center (or you may roll for a random trinket), a set of common clothes, and a pouch containing 10 gp

Characteristics: While sailors are famous for their discourteous behavior, life at sea produces other traits as well. Sailors can be steadfast and reliable companions.

Ship’s Passage:  You can secure free passage on a ship for yourself and your adventuring companions. While onboard the ship, you and your party will be expected to assist in the crew’s duties.

Pirate Variant: You’ve spent time with the most ruthless cutthroats to ever sail the salty seas. You’ve fought bandits and sharks and everything in between in the name of pride and treasure. Those who know of your deeds—or your crew—have nothing good to say about you. 

Bad Reputation Feature Variant: This is an optional feature that ensures that your character has spent time engaging in piracy of the worst kind. Your reputation is so foul that people are often afraid of you.

Life at Sea

You’ll need to decide how your character came to be a sailor. Were you born into a life of piracy? Maybe you spent years on a merchant ship after running away from home.

Or did you grow up in a small fishing village where your father taught you to knot a rope and follow the stars?

Whatever your origin, you’ll need to talk to your DM about your experience as a sailor and figure out what type of ships your character is familiar with. Discuss what role your character had on the vessel.

Were you a boatswain, a cook, or a sailing master? Maybe you were once the captain of your own ship before falling victim to a vicious mutiny.

The possibilities for your character are as open as the sea. By spending time on your character’s backstory, you’ll ensure that you have plenty to draw from when it comes to roleplaying.

Sailors can be militaristic nobles or outrageous outlaws. As pirates, sailors make wonderful, if not unconventional, adventurers.

A Salty Personality

Everyone knows sailors are a rude lot, right? While you’re certain to find a sailor that meets this description during your adventures, not all seamen are uncivil.

Life on the open seas can be as dangerous as it is exciting. Only the truly courageous can survive the dangers.

It’s worth it to take some time and consider your characters ideals, bonds, and flaws. How did  life at sea leave its mark on your character? Did it breed distrust and paranoia, or were you left humbled and accomplished? With the sailor background, you’re free to explore a variety of characteristics. 

Players are free to pick whatever personality traits they want for their characters. If you prefer to let the dice do the work for you, use the following tables:

d8Personality Trait
1My friends know they can rely on me.
2I work hard so that I can play hard when the work is done.
3I enjoy sailing to faraway locations, meeting new people, and trying new things.
4I know that a story is always better when the truth is exaggerated.
5Starting a brawl is my way of meeting new friends.
6A little wager never hurt anyone.
7My language is as rough as the sea in a hurricane.
8I’m not afraid to delegate my work to someone else. In fact, I prefer it that way.
d6Ideal
1Respect: Mutual respect is the only thing that keeps a crew together. (Good)
2Fairness: Everyone must share the workload. (Lawful)
3Freedom: Life is at sea is about going anywhere and doing what you want. (Chaotic)
4Mastery: I see others as prey. (Evil)
5People: I care about my crew more than any law. (Neutral)
6Aspiration: I hope to own my own ship someday. (Any)
d6Bond
1I would never betray my captain.
2Captains come and go. The ship is what matters.
3No ship compares to the first one I sailed on.
4My paramour is out there waiting for me.
5A dastardly captain cheated me out of my profits and I want revenge. 
6I was the victim of a ruthless pirate attack. The murderous rogues killed my captain and crewmates, plundered our ship, and left me for dead.
d6Flaw
1I do whatever I’m told by my superior.
2I will do anything to get out of working.
3I can’t stand to be called a coward. I will do whatever it takes to prove I’m as courageous as anyone.
4I drink like a fish.
5A loose coin purse practically steals itself. 
6To insult my pride is to invite death.

How to Play a Sailor

Giving up the sailor’s life isn’t easy, but there comes a time when every sailor must say goodbye to the freedom and mystery of the deep blue sea and try their fortunes back on land.

While any character can take the sailor background, some classes will have an easier time filling this role. Whether you’re trying to play a swashbuckling pirate or a battle-worn marine, choosing the right class is the key to building a successful character.

Whatever class you choose, your character will be an expert navigator and experienced sailor. These skills are sure to come in handy no matter where your journey takes you.

Rogue

If you want to play a classic pirate, choose the rogue class. As a rogue, you’ll be no stranger to scoundrels, ruffians, and other cutthroats. 

Your time at sea has taught you dangerous lessons. You sleep with a dagger under your pillow and one eye open. No stranger to the pirate’s game, you know that only the strongest survive when the mutineers draw their swords. 

If you see your character as a master swordsman, choose the Swashbuckler roguish archetype. Available in Xanathar’s Guide to Everything, the Swashbuckler archetype is the perfect choice for an elegant duelist who relies on charisma and fancy footwork rather than brute strength. 

Bard

LIfe on the open seas isn’t just for pirates and rogues. Those who seek adventure for its own sake, or for the glory of a good tale, are also drawn to the life of a sailor. And no one tells a better tale than a bard. 

As a bard, your character will have mastered much more than just sailing. A jack-of-all-trades, the bard knows how to inspire and bring the best out of others.

As a sailor, you’ve seen the worst the sea has to offer. Now you sing songs about the storms, sea monsters and dangerous tempests that threatened to send you to a watery grave.

Fighter

If your character spent time aboard a naval ship protecting the seas from pirates, brigands, and rival military forces, you were probably a fighter. As a fighter, your time at sea gave you the chance to study sword and strategy. You can tie a knot as well as you can wrestle. 

Perhaps you were a captain yourself, training daily with your master-of-arms while you hunted pirates off the coast of faraway places. You’ve fought worse than rogues and bandits and have the battle scars to prove it. 

Sailor Features and Variants

The Player’s Handbook offers multiple variants for the sailor background. If your character has indulged in high seas robbery, keeping company with scallywags and ruffians, you should choose the Pirate variant.

As a pirate, people will know to get out of your way. They may have even heard of your exploits. If your character was really awful, you can choose the Bad Reputation feature instead of Ship’s Passage

With this optional Bad Reputation feature, you’ll strike fear into the heart of civilized folks. You can even get away with crimes like stealing, fighting, and breaking down doors.

Most people will do anything to avoid getting on the bad side of a notoriously ruthless pirate, like yourself.

Shipping Out

Many sailors have found themselves caught between devils and the big blue sea. What made you give up your voyages and take up the mantle of adventurer? 

As you explore the world of D&D, you’ll have plenty of opportunities to use your sailing talents. You may need to book passage on a ship or search for treasure on a long-lost island.

Anything can happen in D&D. What if you’re challenged with hunting down a group of bloodthirsty pirates?

Your friends will be happy to have someone around who knows the ropes.

It’s likely fate will see you return to your one true love: the sea.