Pirate Backstory Generator: A Berth, a Rule and a Wish Ashore

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Pirate Backstory Generator: A Berth, a Rule and a Wish Ashore: 30 backstories

Went to sea in a flour barrel, and came out white to the eyebrows. Sails as second mate of a snow who keeps the night watch for choice. Still talks about a wreck on a reef with its bell still ringing. Known by a brass spyglass with a dent the shape of a thumb. Keeps one rule: the cook gets a share and a half, and nobody argues. Wants a roof to hear the weather on, from underneath.

Padlock: keep a part. Arrows: change only that part.

Went to seain a flour barrel, and came out white to the eyebrows
Sails assecond mate of a snow who keeps the night watch for choice
Still talks abouta wreck on a reef with its bell still ringing
Known bya brass spyglass with a dent the shape of a thumb
One rulethe cook gets a share and a half, and nobody argues
Wantsa roof to hear the weather on, from underneath

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Backstory of the day

Went to sea in a flour barrel, and came out white to the eyebrows. Sails as second mate of a snow who keeps the night watch for choice. Still talks about a wreck on a reef with its bell still ringing. Known by a brass spyglass with a dent the shape of a thumb. Keeps one rule: the cook gets a share and a half, and nobody argues. Wants a roof to hear the weather on, from underneath.
Went to sea in the bread room, which is how the cook found out. Sails as cook on a barque that eats in three sittings. Still talks about a fog so thick the watch changed by rope. Known by a dog that barks at land before anyone can see it. Keeps one rule: never sings before noon. Wants a rope walk of their own, long as a street.
Went to sea to make the chandler stop asking when they would. Sails as sailmaker's mate on a fluyt, still learning to thread. Still talks about a parrot that knew a banker's passwords. Known by a lucky cork on a string, from the first ship. Keeps one rule: never swims where they cannot see the bottom. Wants a rope walk of their own, long as a street.
Went to sea asleep in a rowing boat that was not theirs. Sails as sailing master of a xebec who learned on river barges. Still talks about a rainbow at midnight, pale as chalk. Known by tar that never quite leaves the hands. Keeps one rule: reads the weather off the ship's cat. Wants a roof to hear the weather on, from underneath.
Went to sea because the quartermaster shook hands as if it mattered. Sails as cooper on a snow, maker of the crew's only bathtub. Still talks about a bag of seeds that became the ship's garden. Known by a hat with a brim wide enough to keep a chart dry. Keeps one rule: no bananas aboard, not even in a pie. Wants a grandfather's chair by a grandfather's fire.
Went to sea asleep in a rowing boat that was not theirs. Sails as sailmaker's mate on a fluyt, still learning to thread. Still talks about an anchor hauled up with a second anchor caught in it. Known by a ship's cat that sleeps in their hat, worn or not. Keeps one rule: never swims where they cannot see the bottom. Wants an orchard planted in rows as straight as a wake.
Went to sea delivering a pie to a ship that left with the tide. Sails as helmsman on a galleon that takes a mile to turn. Still talks about blue fire along the yards with thunder in the air. Known by a belt buckle the size of a saucer. Keeps one rule: touches a shipmate's collar before a long watch. Wants a workshop mending clocks, since none keep time at sea.
Went to sea because the sea was the only thing they had not tried. Sails as boatswain of a sloop, loud enough for a galleon. Still talks about a crate of spoons when they had been promised silver. Known by a pencil behind each ear and a third in one boot. Keeps one rule: quarrels wait for dry land. Wants a job poling a flat boat across one narrow river.
Went to sea the morning the circus hired a better juggler. Sails as helmsman of a schooner who steers by the feel of the deck. Still talks about crates of spectacles, so now the whole crew can read. Known by a hat with a brim wide enough to keep a chart dry. Keeps one rule: dips the flag to every ship they pass, friend or not. Wants a beehive, because bees sound like rigging in a breeze.
Went to sea asleep in a rowing boat that was not theirs. Sails as carpenter of a brig who talks to the hull. Still talks about a fog they sailed inside for three days on purpose. Known by a set of dominoes with the double six missing. Keeps one rule: one hand, one vote, and the captain's counts the same. Wants to be asked what they do, and answer in one plain word.
Went to sea in a water cask nobody had filled yet. Sails as captain of a sloop, elected by a crew of nine. Still talks about a sandbar the whole crew got out and pushed over. Known by an anchor on the forearm, slightly off level. Keeps one rule: mends a sail the day it tears. Wants a wall to mend, stone by stone, with no hurry in it.
Went to sea in the bread room, which is how the cook found out. Sails as cook on a sloop with one pot and no lid. Still talks about the reef they crossed on the one high tide of the year. Known by initials tattooed wrong and stubbornly kept. Keeps one rule: never lets the water casks fall below half. Wants a bath with hot water and a door that locks.
Went to sea chasing a loose page off the end of a pier. Sails as able seaman on a snow, first aloft in any weather. Still talks about a chain across a river mouth, cleared on the top of a wave. Known by a pig on one foot and a hen on the other. Keeps one rule: reads the weather off the ship's cat. Wants a lane where every neighbour nods and nobody crosses over.
Went to sea under the captain's own bunk, for nine days. Sails as purser on a schooner who counts every share twice, aloud. Still talks about a ship carrying nothing but clocks, all set differently. Known by a dark stone on a thread that always swings north. Keeps one rule: quarrels wait for dry land. Wants a pair of shoes made for their own two feet.
Went to sea selling lemons from a boat that drifted too far out. Sails as sailing master of a xebec who learned on river barges. Still talks about an anchor hauled up with a second anchor caught in it. Known by a crab that walks one pace behind them, sideways. Keeps one rule: washes the figurehead's face before every voyage, for luck. Wants to meet a niece named after their first ship.
Went to sea in a cello case, with the cello left on the quay. Sails as first mate of a ketch, second to nobody but the weather. Still talks about crates of spectacles, so now the whole crew can read. Known by a pencil behind each ear and a third in one boot. Keeps one rule: touches a shipmate's collar before a long watch. Wants an orchard planted in rows as straight as a wake.
Went to sea to escape an apprenticeship to a wig maker. Sails as navigator on a snow who trusts the chip log over the captain. Still talks about a comet the lookout reported, firmly, as a lighthouse. Known by a hat with a brim wide enough to keep a chart dry. Keeps one rule: never sings before noon. Wants a job lighting the street lamps of one small town.
Went to sea thinking the ship was the ferry. Sails as carpenter of a brig who talks to the hull. Still talks about an island that was not there on the way back. Known by a dolphin that meets the ship outside every port. Keeps one rule: counts any albatross as good luck and lets it be. Wants a mill by a stream, for the sound of it.
Went to sea inside a costume trunk, during a game of hide and seek. Sails as quartermaster on a dhow, chosen for dividing things fairly. Still talks about a crate of spoons when they had been promised silver. Known by tying a knot in anything left lying about. Keeps one rule: sings the reply to any shanty, however bad. Wants a pair of shoes made for their own two feet.
Went to sea behind the sail locker, fed by a kind sailmaker. Sails as purser of a galleon, with a quill behind each ear. Still talks about a customs boat that waved them through by mistake. Known by a pig on one foot and a hen on the other. Keeps one rule: shares by the articles, down to the last raisin. Wants an honest paper for every thing they own.
Went to sea under the canvas cover of the ship's longboat. Sails as cabin boy of a brig, runner of errands and gossip. Still talks about a calm they rowed out of, singing, for two days. Known by gloves with the fingertips cut off for rope work. Keeps one rule: the sea bag stays packed, even in the best lodgings. Wants a pair of shoes made for their own two feet.
Went to sea to get away from a town with only one opinion. Sails as cooper on a barque, keeper of the water casks. Still talks about a cabin trunk of sheet music, dried page by page. Known by an oilskin cape that crackles when they walk. Keeps one rule: counts any albatross as good luck and lets it be. Wants a bath with hot water and a door that locks.
Went to sea to get away from a town with only one opinion. Sails as carpenter's mate on a ketch, packing seams with oakum. Still talks about a cabin trunk of sheet music, dried page by page. Known by a tortoise the crew steps over without looking. Keeps one rule: never wakes the off watch for anything but weather. Wants to meet a niece named after their first ship.
Went to sea with a best friend, who went home after one day. Sails as navigator on a brig who draws every coast from memory. Still talks about a round of cheese that outranked the captain. Known by a laugh that carries two ships away. Keeps one rule: calls every hand by the name they chose. Wants to teach schoolchildren to swim, for nothing.
Went to sea to find a father who went the same way. Sails as cooper of a fluyt who can hear a leak through oak. Still talks about crates of spectacles, so now the whole crew can read. Known by the habit of tasting the wind before speaking. Keeps one rule: takes one share, whatever anyone offers. Wants a bed that stays level all night.
Went to sea when a goat they were minding walked up the gangway. Sails as cooper of a fluyt who can hear a leak through oak. Still talks about nine hundred umbrellas bound for a dry country. Known by gloves with the fingertips cut off for rope work. Keeps one rule: touches a shipmate's collar before a long watch. Wants to tell a doubting uncle exactly how far they got.
Went to sea thinking the ship was the ferry. Sails as cooper on a barque, keeper of the water casks. Still talks about a hull found drifting with the table laid for supper. Known by a full-rigged ship across the back, never finished. Keeps one rule: the sea bag stays packed, even in the best lodgings. Wants a hearth that needs no watch kept on it.
Went to sea thinking the ship was the ferry. Sails as quartermaster on a barque who ends every sulk with soup. Still talks about a chart they followed for a month the wrong way up. Known by a scarf long enough to moor a small boat. Keeps one rule: no bananas aboard, not even in a pie. Wants a garden that does not move.
Went to sea among the mail sacks, which they sorted to pass the time. Sails as navigator's mate on a barque, keeper of the sandglass. Still talks about a turtle longer than the jolly boat. Known by a belt buckle the size of a saucer. Keeps one rule: reads the weather off the ship's cat. Wants a reference from a captain who means every word.
Went to sea selling lemons from a boat that drifted too far out. Sails as sailmaker's mate on a fluyt, still learning to thread. Still talks about a customs boat that waved them through by mistake. Known by a five-point star inked on one shoulder. Keeps one rule: never laughs at a seasick shipmate. Wants to be asked what they do, and answer in one plain word.

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Went to sea: all 60 ways to sea

Stowed away 12

among the mail sacks, which they sorted to pass the time Neat stacks of letters, town by town, in a dark hold and one very tidy stowaway.
behind the sail locker, fed by a kind sailmaker A hand passing a crust through a gap between rolled sails.
in a cello case, with the cello left on the quay A cello standing alone on the quay with a luggage label tied to its neck.

Show all 60 ways to sea (57 more)

Stowed away, continued

in a flour barrel, and came out white to the eyebrows A small figure climbing out of a barrel in a cloud of flour, the cook frozen with a scoop.
in a water cask nobody had filled yet The round lid lifted from inside like a hat being raised.
in the bread room, which is how the cook found out Loaves on a shelf, each with one neat corner missing.
in the chain locker, and slept through the leaving Curled on a heap of anchor chain, links printed on one cheek.
inside a crate addressed to a mayor's kitchen A crate with air holes drilled in the shape of a star and one eye at the middle hole.
rolled in a spare sail, at their own request A rolled sail on a sailor's shoulder with two boots sticking out of one end.
under the canvas cover of the ship's longboat Two eyes under a canvas edge and a row of gulls on the rail looking straight at them.
under the captain's own bunk, for nine days A bunk seen from floor level: boots, a dropped book and one hand stealing an apple.
up the mainmast before dawn, and climbed down far from land A tiny figure hugging the masthead while the town shrinks behind.

Signed on 12

at fourteen, saying sixteen Standing on tiptoe inside borrowed boots while a mate squints at them.
because the first mate laughed at their first answer Chin up, arms folded, at a table where a mate is wiping his eyes.
because the quartermaster shook hands as if it mattered A large hand held out across a crew list and a small one being wiped on a shirt first.
the day the family's fishing boat was sold to a neighbour A neighbour at the oars of a familiar skiff and a sea bag packed on the quay wall.
for the promise of one share and three meals a day Counting on fingers at a recruiting table: one, two, three, and a grin.
the morning after the mill shut its doors A mill wheel standing still and a figure walking downhill toward masts.
to escape an apprenticeship to a wig maker A wig block wearing a sailor's cap, left in a shop window as a goodbye.
to make the chandler stop asking when they would A shopkeeper leaning on a counter of rope and lamps, grinning as the door swings shut.
when a crew voted to take on anyone who could read A show of hands on deck and a newspaper held up like evidence.
with a bag of borrowed tools and a straight face A tool bag with somebody else's initials burned into the strap.
with a best friend, who went home after one day Two sea bags at a gangway, one going up and one coming back down.
with an X they have since learned to improve on Draw the crew list: a column of names and one large, proud, crooked X.

Born to it 12

after a cousin who wrote good letters about it A stack of envelopes under one arm, each with a small sketch of a wave in the corner.
as soon as they could reach the tiller Both arms hooked over a tiller, feet off the deck.
because every aunt and uncle already had A family portrait in which everyone but the baby wears sea boots.
because the family boat needed one more pair of hands Counting places at the oars: five rowers, six benches.
before they could walk, so they learned on a slope First steps drawn on a tilted deck, arms out, a ring of sailors ready to catch.
carried aboard in a herring basket A basket on a gangway with a small fist waving out of the top.
in a cradle slung between two deck beams A cradle swinging in time with the hammocks on either side of it.
on a grandfather's boat that smelled of onions Strings of onions hung in the rigging like flags.
on a mother's ship, paid in lessons A captain in a good hat pointing at a knot, a child copying it with a frown.
on the tide they were born on, or so the crew says A midwife being rowed ashore, waving, as the sails fill behind her.
to bring a parent's sea boots home, and kept going A pair of boots far too big, carried up a gangway by the laces.
to find a father who went the same way A child's drawing of a ship held up against each real ship in a port.

By mistake 12

after going aboard to complain about the noise A townsman in a nightcap shaking a fist on deck while the gangway is hauled in.
after stepping aboard to ask the way to the post office A parcel under one arm on a moving deck and a sailor pointing back at the shrinking quay.
as the tailor still measuring the captain's sleeve A tape measure round a captain's arm and open sea in the window behind.
asleep in a rowing boat that was not theirs A rowing boat towed behind a tall ship, its passenger still snoring under a coat.
because the tide and the rent collector arrived together One figure striding down a lane with a ledger, another stepping calmly onto a deck.
chasing a loose page off the end of a pier Mid-leap between pier and deck, one hand out for a sheet of paper in the wind.
delivering a pie to a ship that left with the tide A pie held level at arm's length as the quay slides away behind.
inside a costume trunk, during a game of hide and seek A lid opening on a child dressed as a king, surrounded by sailors and no seekers.
on a ship they had only come to paint a name on Hanging over the stern in a rope sling, brush in hand, the town getting smaller.
selling lemons from a boat that drifted too far out A small boat of lemons bumping against a tall hull, both a long way from land.
thinking the ship was the ferry Holding up a ferry ticket to a crew that has gone very quiet.
when a goat they were minding walked up the gangway A goat at the very front of the ship like a figurehead and its keeper climbing after it.

Leaving something 12

after losing a spelling contest very badly A slate with a long word crossed out many times, left on a quay wall.
because the sea was the only thing they had not tried A list of crossed-out trades pinned to a wall, the last line still wet.
because the town's chimney smoke made them sneeze Looking back at smoking chimneys with a handkerchief, forward at the sea with relief.
the morning the circus hired a better juggler Three dropped clubs on a quay and one striped stocking in a sea bag.
rather than inherit a button shop Drawers of sorted buttons, and one drawer left open and empty.
to avoid a second term as town crier A handbell set down on the rim of a fountain and a figure tiptoeing away.
to get away from a town with only one opinion A row of identical shutters and one open window with a rope of bedsheets.
to get clear of a rhyme the town made about them Children on a pier shouting something that the wind is kindly taking away.
to have a hammock to themselves, after a bed shared by five Five heads in a row in one bed, ten feet out of the bottom, and the middle one wide awake.
to prove a schoolbook wrong about the horizon A book open at a flat map, a pencil line drawn right off the page.
the week their landlady took up the trombone A brass horn out of an upstairs window and a hammock already rolled under one arm.
when the town band would not have them A drum left on a doorstep with the sticks crossed on top.

How this list was compiled: Original list written for Draw This Next, October 2026. Every way to sea is by choice, by family or by mistake: nobody here is carried off, pressed or taken from another ship. The notes on what to draw are our own suggestions. Licence: own work

Sails as: all 60 berths

Galley and stores 15

cook of a brigantine, voted in for a single good stew A ladle carried in the belt like a badge of office.
cook of a cutter too small to have a galley A stove lashed to the deck beside the mast and a cook leaning with every wave.
cook on a barque that eats in three sittings Three masts, three sittings. Draw a slate with the watches chalked beside the soup.

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Galley and stores, continued

cook on a dhow who trades recipes in every port A recipe book stuffed with loose leaves in a dozen kinds of handwriting.
cook on a lugger, famous for hardtack that bends A cracker being flexed between two hands while the crew looks on in wonder.
cook on a sloop with one pot and no lid One mast, one pot. Draw the plate that serves as a lid, held down with a spoon.
cook's mate on a xebec, peeler of ten thousand onions A hill of onion skins and one small figure in the middle of it, undefeated.
cooper of a fluyt who can hear a leak through oak A round-bellied cargo ship and a figure knocking along a row of casks.
cooper on a barque, keeper of the water casks A mallet in the hand and an ear laid against a barrel, listening.
cooper on a ketch that carries more barrels than crew Barrels lashed along both rails of a two-masted boat, numbered in chalk.
cooper on a snow, maker of the crew's only bathtub Half a great cask on deck with a pair of knees showing over the rim.
purser of a brig, trusted because they cannot keep a secret Mid-whisper behind a hand to the whole crew at once.
purser of a galleon, with a quill behind each ear A tall many-decked ship behind, a ledger in front, cuffs black to the elbow.
purser on a schooner who counts every share twice, aloud Coins in small equal stacks along a table edge, a finger hovering over each.
purser on a yawl whose strongbox is a tea caddy A dented caddy with a padlock far too big for it.

Rope, sail and timber 15

able seaman on a snow, first aloft in any weather Already at the masthead while the others are still looking for their boots.
able seaman on a xebec, the fastest splicer aboard Two rope ends becoming one in the fingers, done without looking.
boatswain of a lugger, first to notice anything loose A thumb testing a lashing in passing, without breaking step.
boatswain of a sloop, loud enough for a galleon One mast and one enormous voice. Draw the gulls leaving the rigging.
boatswain on a brig who knows every rope by name Pointing up from line to line along the deck, a new hand writing the names down.
boatswain on a galleon with a deck crew of forty A slate of watches so long it reaches the knees.
carpenter of a brig who talks to the hull Palm flat on the timbers, head tilted, as if waiting for an answer.
carpenter on a dhow, the only one who knows her seams Running a thumbnail down a long thin hull, counting under the breath.
carpenter on a sloop that is mostly patches A hull drawn like a quilt, every board a slightly different age.
carpenter's mate on a ketch, packing seams with oakum Tarred strands trailing from a pocket and a mallet in the belt.
sailmaker of a schooner who patches in bright thread Sails with seams you can follow from the shore, like handwriting.
sailmaker on a barque with three masts to dress Cross-legged on deck in a drift of canvas, three bare masts waiting above.
sailmaker on a brigantine, never without a needle A curved needle through the hat brim and a hank of twine round the neck.
sailmaker's mate on a fluyt, still learning to thread Tongue between teeth, a needle held up to the sky to find its eye.
shantyman on a barque, on a full share for the voice Standing on a hatch cover, mouth wide, the crew answering in chorus.

Helm, chart and lookout 15

coxswain of the longboat on a brig, steady in any surf Standing in the stern of a ship's boat, one hand on the steering oar.
helmsman of a cutter, quick as the boat A tiller under one arm and an apple in the other hand.
helmsman of a schooner who steers by the feel of the deck Barefoot at the wheel, eyes shut, smiling.
helmsman on a fluyt who hums the course Notes drawn over the wheel in place of compass points.
helmsman on a galleon that takes a mile to turn Leaning on a great wheel with the whole body, the wake a slow curve behind.
lookout of a ketch who calls the weather before the sea Nose lifted to the wind like a dog, one hand already pointing.
lookout on a galleon, who brings a book up A crow's nest with a cushion, a book and a ribbon to mark the page.
lookout on a sloop whose one mast is a short one Standing on a barrel at the masthead for the extra height.
navigator of a dhow who reads the stars like a street One arm raised at the night sky, counting off turnings.
navigator on a brig who draws every coast from memory A sheet with coffee rings marked as islands and named honestly.
navigator on a snow who trusts the chip log over the captain A wooden chip on a knotted line running out over the stern, a sandglass in the hand.
navigator's mate on a barque, keeper of the sandglass Asleep on a stool with the glass run out, a mate about to cough politely.
sailing master of a brigantine, patient when nobody agrees A calm face over a chart while everyone else points in different directions.
sailing master of a xebec who learned on river barges Reading the shade of the water over the rail as others read print.
sailing master on a lugger who has been lost exactly once A single cross on a chart marked with a date and nothing else.

Voted in, or youngest aboard 15

cabin boy of a brig, runner of errands and gossip Running along a deck with a tray, an ear turned to every doorway.
captain of a brigantine, voted out twice and back in thrice A captain's coat hung on a peg with tally marks chalked on the wall beside it.
captain of a lugger that carried coal until last year Black dust still in every seam of a lug-rigged boat, a bold new flag above.
captain of a schooner who still stands a watch like anyone A captain coming on deck at four in the morning, coat over nightshirt, yawning.
captain of a sloop, elected by a crew of nine Nine raised hands and one startled face. The hat does not fit yet.
first mate of a ketch, second to nobody but the weather Hands behind the back on a small deck, reading the clouds.
mate on a galleon, in charge of the third deck only A lamp on a low deck and a chalk line that marks where the authority ends.
quartermaster of a fluyt who can say no to the captain A firm shake of the head across a table from a much larger hat.
quartermaster of a schooner, keeper of the articles A rolled paper in an oilcloth tube worn on a cord round the neck.
quartermaster of a yawl, which makes them half the crew Two figures on a small two-masted boat, one of them wearing every badge.
quartermaster on a barque who ends every sulk with soup Standing between two sulking sailors, serving each exactly the same.
quartermaster on a dhow, chosen for dividing things fairly Dividing a melon with great ceremony while the crew watches the cut.
second mate of a snow who keeps the night watch for choice Alone on deck under stars with a mug of something hot.
ship's boy on a cutter, already the best climber aboard Sitting on the very end of a spar, swinging both legs.
ship's boy on a xebec, halfway through learning the compass A compass card held in both hands and a finger stuck at north-east.

How this list was compiled: Original pairings written for Draw This Next, October 2026. Every vessel type and every post is a real one, checked on 2026-10-01 against Wikipedia: https://en.wikipedia.org/wiki/Sloop (one mast), https://en.wikipedia.org/wiki/Ketch, https://en.wikipedia.org/wiki/Brig, https://en.wikipedia.org/wiki/Brigantine and https://en.wikipedia.org/wiki/Snow_(ship) (two masts each), https://en.wikipedia.org/wiki/Barque (three or more masts), https://en.wikipedia.org/wiki/Schooner, https://en.wikipedia.org/wiki/Lugger, https://en.wikipedia.org/wiki/Cutter_(boat), https://en.wikipedia.org/wiki/Yawl, https://en.wikipedia.org/wiki/Galleon, https://en.wikipedia.org/wiki/Fluyt, https://en.wikipedia.org/wiki/Xebec and https://en.wikipedia.org/wiki/Dhow for the vessels; https://en.wikipedia.org/wiki/Governance_in_18th-century_piracy for the elected captain and quartermaster, the sailing master, boatswain, mates, carpenters and ship's boys; and the articles Cooper (profession), Sailmaker, Helmsman, Coxswain, Lookout, Cabin boy, Able seaman, Chief cook, Navigator, Purser, Sea shanty (for the shantyman), Oakum, Careening, Chip log and Hardtack for the rest. No real ship, crew or port is named, and the master gunner and the surgeon were left out. The notes on what to draw are our own suggestions. Licence: own work

Still talks about: all 60 sea stories

Cargoes 12

a cargo of kites, flown from every mast on the way home Paper kites high above every masthead, one small sailor holding each string.
a cargo of nutmeg that scented the crew for a year Sailors asleep on brown sacks, every one of them smiling.
a hold of mirrors that lit the whole bay at noon Squares of light thrown up onto the sails and the cliffs.

Show all 60 sea stories (57 more)

Cargoes, continued

a hundred sacks of pepper and a week of sneezing The whole watch with kerchiefs tied over their noses, eyes streaming.
a round of cheese that outranked the captain A wheel of cheese in the captain's chair with a hat on it.
a ship carrying nothing but clocks, all set differently A hold of open crates and a hundred clock faces that disagree.
a whole cargo of left shoes and not one right A sailor holding up two shoes and slowly understanding the problem.
barrels of ink that turned the wake black for a mile One split barrel at the stern and a dark ribbon trailing behind the ship.
bolts of yellow silk, now a nightshirt for every hand aboard A whole watch hauling on one rope at dawn, all in bright yellow nightshirts.
crates of spectacles, so now the whole crew can read A row of sailors on a bench in round glasses, sharing one newspaper.
forty crates of oranges, eaten before they could be sold Peel in long curls over the side and a very quiet, very sticky crew.
nine hundred umbrellas bound for a dry country A deck of open umbrellas in the sun, the ship like a strange flower bed.

Wrecks and salvage 12

a cabin trunk of sheet music, dried page by page Sheets of music clipped all through the rigging, drying in the wind.
a chart case from a wreck, with every chart blank Unrolled sheets of clean paper and a navigator looking at them hungrily.
a corked bottle holding a note in their own handwriting A small roll of paper, and a sailor reading it with one hand over the mouth.
a figurehead they raised and gave a seat at dinner A carved wooden lady at the end of a mess table with a bowl in front of her.
a hull found drifting with the table laid for supper A cabin table with six places set and a candle burned to nothing.
a mast standing out of a sandbar at low tide A lone mast in wet sand with a gull on top and footprints leading up to it.
a ship's boat full of pineapples and nobody else An open boat riding low, heaped with spiky fruit, bumping gently alongside.
a ship's wheel brought up from four fathoms, one spoke short A weed-hung wheel propped against the mast and a carpenter whittling a new spoke for the gap.
a sunken chest that held one child's tin soldiers A great iron-bound chest open on deck, and a row of tiny painted soldiers in one corner.
a wreck on a reef with its bell still ringing A mast top above the surf and a bell swinging with each wave.
a wreck so old the crabs had moved in by rank Crabs at every window of a sunken stern, the largest in the captain's cabin.
an anchor hauled up with a second anchor caught in it Two anchors locked together swinging over the side, the crew scratching their heads.

Seen at sea 12

a calm so flat they played skittles on deck Wooden pins standing on a level deck, the sails hanging like curtains.
a comet the lookout reported, firmly, as a lighthouse A long-tailed light low over the horizon and a lookout pointing, quite sure.
a fog so thick the watch changed by rope Two hands meeting along a taut line, nothing else of either sailor showing.
a night the sea lit up wherever an oar touched it A ring of pale light round each oar blade and the rest of the sea dark.
a rainbow at midnight, pale as chalk A pale arch over a dark sea under a full moon, white chalk on blue paper.
a tern that rode the stern rail for a week A small neat bird on the rail, facing backward, as if keeping its own log.
a turtle longer than the jolly boat A broad shell alongside a small boat, the rowers resting their oars to stare.
a waterspout that set the ship down facing home A twisting column of water in the distance and a compass needle swinging round.
a whale that swam beside them for eleven days One long dark back level with the rail and a ship's boy waving at it.
an island that was not there on the way back A navigator's finger on a chart and nothing but water ahead.
blue fire along the yards with thunder in the air A soft glow at every masthead and spar tip, and a crew looking up in silence.
flying fish landing in the frying pan unasked A cook holding out a pan at the rail like someone catching rain.

Narrow escapes 12

a calm they rowed out of, singing, for two days Long sweeps over the sides of a tall ship, every mouth open.
a chain across a river mouth, cleared on the top of a wave A hull lifted high, the chain passing under in a trough of green water.
a chart they followed for a month the wrong way up A navigator turning a sheet slowly round while the captain watches.
a customs boat that waved them through by mistake An officer saluting from a small boat while the crew salutes back, eyes wide.
a fog they sailed inside for three days on purpose The stern of a ship vanishing into white, a lookout waving goodbye.
a sandbar the whole crew got out and pushed over Sailors waist deep along both sides of a hull, shoulders to the hull.
a signal they answered wrong and were thanked for Two strings of flags on two ships, and one puzzled, grateful wave.
a storm that took the sails and left the washing Bare yards, and a row of shirts still pegged along one line.
the day they sold a port official his own barrel of pickles A barrel changing hands on a quay, a sailor's face held very straight.
the reef they crossed on the one high tide of the year Coral a hand's width under the keel and the whole crew holding its breath.
slipping past a blockade dressed as a floating market Awnings over the rails and the whole crew in aprons, selling melons.
the week they hid the whole ship behind a waterfall A curtain of falling water and the tip of one mast just showing through.

Small hauls, long stories 12

a bag of seeds that became the ship's garden Bean plants climbing the shrouds from a row of buckets.
a barrel organ that plays only in rough weather A small crank organ sliding on a table as the cabin tilts, playing by itself.
a crate of spoons when they had been promised silver A sailor holding a tin spoon up to the light, still hoping.
a governor's wig, returned by post A parcel on a doorstep, neatly tied, with a polite note under the string.
a map that led, correctly, to a very good well A cross on a map, a hole in the ground and a crew drinking from their hats.
a parrot that knew a banker's passwords A bird on a perch saying something that makes a whole crew lean in.
a rocking horse every hand has ridden once, in secret A painted rocking horse on deck at night and a large sailor looking both ways first.
a ship in a bottle that looks exactly like theirs A small bottle held up against the real thing, both with the same crooked mast.
a single pearl in an oyster they nearly threw back An open shell on a palm and a ring of heads bent over it.
a walking cane with a map rolled inside it A hollow cane tipped up and a tight scroll sliding out into a waiting hand.
the best hat any of them had ever seen A hat on a barrel in a shaft of light, the crew standing round it bareheaded.
one gold coin with a hole in it, worn in turns A coin on a cord passed from one neck to the next at the change of watch.

How this list was compiled: Original list written for Draw This Next, October 2026. Each entry is a cargo, a wreck, a sight or a narrow escape, told for the story and not for the taking: no ship is attacked in any entry and nobody is hurt. The sights are real ones (a waterspout, the glow at a masthead that sailors call St. Elmo's fire, a sea lit by tiny glowing creatures, a rainbow made by moonlight, flying fish), checked on 2026-10-01 against https://en.wikipedia.org/wiki/Waterspout, https://en.wikipedia.org/wiki/St._Elmo%27s_fire, https://en.wikipedia.org/wiki/Bioluminescence, https://en.wikipedia.org/wiki/Moonbow and https://en.wikipedia.org/wiki/Flying_fish. The notes on what to draw are our own suggestions. Licence: own work

Known by: all 60 marks

Clothes 12

a belt buckle the size of a saucer Polished enough to signal with. Draw the flash of light it throws.
a faded coat with brand new elbows every year Elbow patches in fresh canvas on a coat gone the colour of fog.
a governor's coat with the cuffs turned back four times Gold buttons level with the knees and a hem that sweeps the deck.

Show all 60 marks (57 more)

Clothes, continued

a hat with a brim wide enough to keep a chart dry A chart being read under the hat in the rain, the reader perfectly dry.
a knitted cap with a bobble the size of an apple A wool cap with one enormous bobble, bouncing as they climb the rigging.
a red sash that is really a tablecloth A fringe at one end and a faint ring where a teapot once stood.
a scarf long enough to moor a small boat The loose end trailing behind in every wind like a pennant.
a striped shirt that can be seen from the next ship Broad red and white stripes on a far deck, the only thing anyone can make out.
a waistcoat sewn from a signal flag Bold blocks of red and yellow that mean something to anyone who reads flags.
an oilskin cape that crackles when they walk Stiff folds standing away from the body, rain running off in ropes.
gloves with the fingertips cut off for rope work Bare fingertips busy with a line, the rest of the hand snug in wool.
sea boots that do not match and never did One tall and one short, one black and one brown, both well loved.

Ink and tar 12

a blue dot on the wrist for each crossing of the equator A short row of dots, counted off proudly for any new hand.
a compass rose inked on the back of one hand They turn the whole hand, not the head, when asked the way.
a five-point star inked on one shoulder Each point shaded half dark and half light, like the star on a chart.
a full-rigged ship across the back, never finished Hull and two masts in ink, the third mast only sketched.
a pig on one foot and a hen on the other Bare feet on a wet deck, the two small animals facing each other.
a swallow tattooed at the base of one thumb Small enough to hide with the other hand. It shows when they point.
a thumbnail kept long for opening oysters One long nail on a working hand, sliding into the hinge of a shell.
an anchor on the forearm, slightly off level Drawn at sea by a friend during a swell, and it shows.
green stains from a picture nobody has been shown A green thumb and forefinger and a small board pushed quickly under a coat.
initials tattooed wrong and stubbornly kept Two letters on the arm, one of them clearly somebody else's.
tar that never quite leaves the hands Dark lines in every crease of the palm, like a second set of fingerprints.
the words HOLD FAST across the knuckles Four letters on each fist, read when both hands grip a rope.

Habits 12

a laugh that carries two ships away Sailors on a far deck turning their heads toward a sound.
a salute to every gull, in case it is someone Two fingers to the hat brim, and a gull that seems to expect it.
a song they hum without knowing, always the same one Notes drifting behind them along a quay, and people beginning to join in.
a walk that still rolls on dry land Draw them on a level street, leaning as if the street might tilt.
choosing whichever seat has a view of the sky The chair by the window in every room, head tilted to read the clouds.
counting heads at every change of the watch Pointing at each sailor in turn as one watch goes below.
the habit of tasting the wind before speaking Tongue out a little, eyes narrowed, facing the weather.
saying port and starboard indoors Pointing a dinner guest toward the door with a sea word and no apology.
sleeping with one hand round a rope, even ashore Asleep in a chair with a bell pull wound twice round one fist.
squinting at anything far off, even indoors One eye shut, a hand shading the other, reading a sign across a room.
standing with one foot on anything raised A boot on a barrel, a step, a coil of rope. Always the same boot.
tying a knot in anything left lying about Bootlaces, curtain cords and a guest's scarf, all neatly knotted.

In the hand 12

a brass spyglass with a dent the shape of a thumb The dent sits exactly where the thumb goes. Draw the grip.
a dark stone on a thread that always swings north A pebble hung from one finger, turning slowly, a crew watching it settle.
a folding ruler for measuring sails, waves and new hands A hinged wooden rule held upright beside a nervous ship's boy.
a jaw harp that plays one note in three moods A small iron frame held at the lips and one finger plucking.
a knotted cord said to hold three winds Three thick knots on a short cord at the belt, the last one never touched.
a long leather map tube used for carrying sausages A stiff tube tipped up at dinner and a string of sausages sliding out.
a lucky cork on a string, from the first ship A plain bottle cork gone dark with handling, tied at the throat with tarred string.
a lump of beeswax thumbed into the shape of a whale A dark yellow lump on a palm: a tail, a back and one thumbprint for an eye.
a marlinspike worn on a lanyard like a medal A polished steel cone on a cord, used for rope and for pointing at things.
a pencil behind each ear and a third in one boot Reaching up without looking and always finding one.
a sea chest with a row of houses carved on the lid A lid with a little street cut into it, one window inlaid with shell.
a set of dominoes with the double six missing Tiles laid end to end along a rail and a gap where the last one should go.

Company kept 12

a crab that walks one pace behind them, sideways A small crab on a deck keeping exact step with a pair of sea boots.
a dog that barks at land before anyone can see it Front paws on the forward rail, nose working, tail straight out.
a dolphin that meets the ship outside every port A fin beside the ship and a sailor leaning far over the rail to say hello.
a gull that follows from port to port The same bird on the same rail in three different drawings of three ports.
a hen that lays only at sea A hen in the crook of an arm on a rolling deck, perfectly calm.
a lizard that sleeps in the compass box at night A small tail curling out from under a brass lid.
a monkey that can tie a bowline and nothing else A small figure in the rigging beside one perfect knot and several disasters.
a mouse the cat has agreed to ignore A cat asleep on a coil of rope and a mouse asleep in the middle of the coil.
a pelican that taps on the porthole to be let in at night A long bill at a round window, tapping, and a sleepy hand reaching for the catch.
a ship's cat that sleeps in their hat, worn or not A hat on a head with a tail hanging down behind like a second plume.
a ship's goat that has outlived three captains A goat standing on a hatch cover with the air of a senior officer.
a tortoise the crew steps over without looking A slow shell crossing the deck, the ship's name in paint on its back.

How this list was compiled: Original list written for Draw This Next, October 2026. Each entry is something a viewer could pick the character out by: clothes, ink, a habit, a thing in the hand or the company they keep. No entry is an injury. The sailors' tattoos named here (a swallow, the words HOLD FAST across the knuckles, a pig and a hen, an anchor, a star to find the way home, a full-rigged ship) were checked on 2026-10-01 against https://en.wikipedia.org/wiki/Sailor_tattoo and https://en.wikipedia.org/wiki/Sailors%27_superstitions, the marlinspike against https://en.wikipedia.org/wiki/Marlinspike and the ship's cat against https://en.wikipedia.org/wiki/Ship%27s_cat. The notes on what to draw are our own suggestions. Licence: own work

One rule: all 60 rules

Superstitions 12

a coin under the mast before any voyage Kneeling at the foot of a mast, pressing a coin into the step with a thumb.
a red sky at morning means a day in port A red dawn in a porthole and boots being put back under the bunk.
counts any albatross as good luck and lets it be A great white bird gliding past the rail and the whole watch stopped to look.

Show all 60 rules (57 more)

Superstitions, continued

never renames a ship, however silly the name A stern with a ridiculous name in fresh paint and a proud figure beside it.
never sails with an odd number of spoons aboard A cook counting spoons into a drawer in pairs, and the last one with no partner.
never sets sail with washing still on the line Shirts being hauled in hand over hand as the anchor comes up.
no bananas aboard, not even in a pie A cook at the gangway turning back a fruit seller with one raised hand.
picks up every mermaid's purse on a beach, just in case A dry black pouch with curled horns at each corner, found on a beach.
reads the weather off the ship's cat A cat chasing its tail on deck and a sailor already reefing the sail.
touches a shipmate's collar before a long watch Two fingers on a broad collar in passing, as lightly as a bird landing.
washes the figurehead's face before every voyage, for luck Leaning far over the bow with a wet cloth, wiping the nose of a painted wooden figure.
waves to the last lit window on shore, for luck One arm up at the stern toward a small yellow light on a headland.

For the ship 12

the bilge stays drier than the biscuit A lamp held low in the bottom of the hull, showing clean dry timber.
careens the hull every spring, however good the wind A ship lying on its side on a beach, the crew scraping weed off the hull.
lamps out at eight in the evening, no arguments One hand cupping a flame, the other already lifting to pinch it.
mends a sail the day it tears Sewing by the last of the light, the needle flashing.
never leaves port on a knot they did not tie Going round the deck at dusk, tugging each line once.
never lets the water casks fall below half A chalk line halfway up a barrel, and a level eye checking it.
never moors upwind of another ship's cooking A ship gliding past a smoking galley chimney to tie up further along.
oils every pulley on the first of the month A sailor aloft with an oil can, working along a row of pulleys one by one.
scrubs the deck before breakfast, whatever the weather On hands and knees with a scrubbing stone in sideways rain.
sounds the depth twice, always A lead weight on a marked line swung out a second time from the rail.
stows every line the same way, even if it is not theirs A deck of neat flat spirals, all turning the same direction.
writes the log every night, even on dull days A page that says only "Wind fair. Soup." in careful handwriting.

For the crew 12

calls every hand by the name they chose A crew list with several names crossed out and better ones written in.
knows every shipmate's birthday, and something gets baked A row of dates scratched inside a locker lid and a cook being whispered to.
never laughs at a seasick shipmate A bucket held steady and a face turned politely to the horizon.
never wakes the off watch for anything but weather A hand raised to knock on a hammock post, then lowered.
one hammock is always left free for a guest An empty hammock with a folded blanket in it and nobody's name.
quarrels wait for dry land Two sailors glaring across a deck and a third pointing at the horizon.
saves the night watch a hot potato, wrapped in a cloth A bundle in a cloth, steaming, carried up the rigging in the teeth.
the ship's boy is never sent aloft in a blow A big hand on a small shoulder at the foot of the rigging.
sings the reply to any shanty, however bad Mouth open on the chorus while hauling, wincing at the verse.
teaches one knot to anyone who asks Two pairs of hands on one rope, the slower pair copying.
tells the watch below one story a night, and only one A lantern, a ring of hammocks and one finger held up: just the one.
writes home for any shipmate who cannot A pen moving while a large sailor dictates, twisting a cap in both hands.

For themselves 12

climbs the highest hill in any new port before eating Halfway up a steep street past a row of food stalls, the ship a toy in the harbour below.
dips the flag to every ship they pass, friend or not A flag lowered a hand's width across the water to a deck that does not answer.
never boasts about a voyage until both feet are ashore One foot on the gangway, one on the quay, mouth just beginning to open.
never goes ashore without a list, and keeps to it A scrap of paper held in the teeth while both arms carry exactly what it says.
never lies about the size of a fish Hands held a modest distance apart, the listeners a little disappointed.
never sings before noon Mouth firmly shut at the morning haul while everyone else is in full voice.
never sleeps through a landfall, whatever the hour Wrapped in a blanket at the rail in the small hours, watching a grey coast come up.
never swims where they cannot see the bottom Toes over the edge of a boat above clear green water, checking.
one locked box that nobody may ask about A small box under the hammock, tied shut with a different hitch each week.
says good night to the sea, out loud Leaning on the stern rail at dusk, lips moving, hat in hand.
the sea bag stays packed, even in the best lodgings A tidy room at a lodging house and a sea bag by the door, strings already tied.
stands the same watch as the newest hand, in any weather Two figures at the rail in the rain, one a head shorter, both awake.

How this list was compiled: Original list written for Draw This Next, October 2026. A pirate crew really did write its own rules: the articles of agreement gave each hand a vote and a set share, were signed or marked by everyone and were posted on the cabin door, and a doubtful cargo was sold before it was divided (https://en.wikipedia.org/wiki/Pirate_code and https://en.wikipedia.org/wiki/Governance_in_18th-century_piracy, read 2026-10-01). The sailors' beliefs used here (no bananas aboard, bad luck to rename a ship, good luck to see an albatross and let it be, a coin under the mast, a ship's cat that foretells wind and rain, a red sky at morning, a touch on a sailor's collar, a mermaid's purse from the beach) are from https://en.wikipedia.org/wiki/Sailors%27_superstitions and https://en.wikipedia.org/wiki/Mast_stepping, read the same day. Lamps out at eight and quarrels kept for the shore are in one crew's articles as printed in 1724, and a common fund is in the second article named above; the rest of the rules were written for this list. Rules about whistling, Fridays and the number thirteen were left out because another page of this family has them. The notes on what to draw are our own suggestions. Licence: own work

Wants: all 60 wishes ashore

A trade on land 12

a bakery with a blue door and no stairs A shopfront drawn from memory on the back of a chart, door inked in blue.
a chandler's shop that gives credit to the young A counter, a ledger and a jar of ship's nails sold one at a time.
a job lighting the street lamps of one small town A long pole with a flame at its tip and a row of lamps coming alive down a hill.

Show all 60 wishes ashore (57 more)

A trade on land, continued

a job poling a flat boat across one narrow river A flat boat on a rope across a stream, both banks in the same picture.
a kite shop on a windy headland Paper shapes strung along a fence, pulling at their strings.
a market garden that sells only what is in season Rows drawn as neatly as rigging, a scarecrow in a sea coat.
a rope walk of their own, long as a street A long low shed with one strand of rope running its whole length.
a stall selling soup to people who come home cold A steaming pot under an awning and a queue in wet coats.
a workshop mending clocks, since none keep time at sea A bench of open clocks all ticking together for once.
a yard that builds small boats for other people's children A row of little hulls on trestles, each with a name chalked on.
to paint signs for shops, with every letter level A ladder, a pot of paint and a word half finished above a door.
to teach schoolchildren to swim, for nothing A row of small heads in a millpond and one large one counting them.

A clean name 12

a lane where every neighbour nods and nobody crosses over Walking past a row of doorsteps, every head nodding, nobody stepping away.
a letter that says every debt is paid in full A short letter read three times, then pinned up where it can be seen.
a library ticket in a town that keeps its books A small ticket held like a treasure in front of a wall of spines.
a line in the town register that says what they did well A big open book and a clerk writing slowly with a good pen.
a pardon with their real name spelled right A sealed paper, and a finger checking each letter of one long name.
a reference from a captain who means every word A folded sheet in an inside pocket, taken out and unfolded at the creases.
an honest paper for every thing they own A sea bag emptied on a bed beside a neat stack of bills, each with a stamp.
their old name back, said by someone who knew it A doorway, a pause and a mouth just opening on a word.
to be asked what they do, and answer in one plain word A caller at a gate with a basket, and an answer tried out under the breath.
to be struck off one particular wanted list A notice board with one square of clean wood where a paper used to be.
to vote in a town, with a pebble like anyone else A hand over a jar, a pebble falling, a place in a queue of townsfolk.
to walk past a customs house and be bored Strolling by a tall doorway with hands in pockets, yawning.

Someone waiting 12

a grandfather's chair by a grandfather's fire An empty chair with a blanket over one arm, kept dusted.
to buy a friend the supper promised ten years ago Two places at a table and a note on one plate that says only a date.
to dance at a brother's harvest supper, late but there Coming through a barn door in sea boots as the music turns.
to give a mother back the shawl she lent for one cold night A shawl folded small at the bottom of a sea chest, wrapped in paper against the salt.
to hear a grandmother say the sea was a fair choice Two figures on a breakwater, one pointing out to sea, both nodding.
to meet a niece named after their first ship A small girl being told why her name is painted on a boat.
to read their letters aloud to the one who kept them A ribboned bundle on a table and two chairs pulled close.
to return to a dog that still watches the road A dog on a hilltop, ears up, and a far figure with a sea bag.
to see a sister who thinks they were lost at sea A woman at a door with a hand to her mouth and flour to the elbows.
to show a child the shell they carried round the world A small ear and a big shell, and a tarred hand holding it steady.
to tell a doubting uncle exactly how far they got A globe turned slowly on a kitchen table and an uncle's eyebrows going up.
to thank the cook of their first ship, in person A knock at a galley door and a loaf held out as a gift.

A piece of ground 12

a beehive, because bees sound like rigging in a breeze An ear tilted toward a straw hive, a faraway look.
a garden that does not move Kneeling with both palms flat on a bed of soil, eyes closed.
a hill high enough to see the weather coming A bench on a summit and a figure pointing out a cloud to whoever sits beside them.
a house with a door that faces away from the sea A cottage on a hill, back turned to the water, a path running inland.
a mill by a stream, for the sound of it A wheel turning slowly and a hammock slung where the noise is best.
a pond small enough to row across in four strokes A tiny boat on a tiny pond, the oars nearly touching both banks.
a tree to sit under that they planted themselves A sapling, a stool and a great deal of patience.
a wall to mend, stone by stone, with no hurry in it A gap in a field wall and a sorted heap of stones beside it.
a well of their own, with sweet water A bucket coming up brim full and a face reflected in it.
an island of their own with nothing buried on it A small green island on a chart, marked only with a kettle.
an orchard planted in rows as straight as a wake Young trees tied to stakes with sailor's knots.
one field, one cow and no weather that matters Leaning on a gate in drizzle, perfectly content.

Plain comforts 12

a bath with hot water and a door that locks A tub, a towel on a chair and a sea coat hung on the latch.
a bed that stays level all night A four-post bed drawn with a spirit level resting on the pillow.
a book read to the last page without a squall A thumb holding a place three pages from the end.
a hearth that needs no watch kept on it Boots off, feet toward the flames, a log settling.
a kettle that is theirs, and time to wait for it A kettle just beginning to sing and nobody hurrying it.
a pair of shoes made for their own two feet A cobbler tracing round a bare foot on brown paper.
a roof to hear the weather on, from underneath Lying on a floor looking up, hands behind the head, rain beyond the tiles.
a table that does not need a rail round the edge A full bowl sitting still in the middle of a plain wooden table.
a window that opens on something green A sash thrown up on a meadow and both elbows on the sill.
an egg from a hen that has never been to sea A boiled egg in a cup and a spoon raised over it with respect.
butter that was never salted for a voyage A loaf and a pale pat of butter on a dish. Draw the pause before the first bite.
to sleep until they wake, with nobody shaking them A hammock in sunlight, a hat over the face, the morning half gone.

How this list was compiled: Original list written for Draw This Next, October 2026. Every wish is small enough to draw and none of it is revenge: a trade, a clean name, a person, a piece of ground or a plain comfort the sea does not allow. The notes on what to draw are our own suggestions. Licence: own work

How it works

This pirate backstory generator deals a sea life in six parts: how they went to sea, their post and vessel, the story they still tell, what they are known by, their one rule and a wish ashore. Nobody is hurt.

Read the full guide

Draw the berth first

Every result names a real post on a real kind of vessel, such as cook on a sloop or sailmaker on a brigantine, so the job gives you the hands and the ship gives you the background. A sloop has one mast, a brig two, a barque three or more. The lists below the tool give each entry a note on what to draw.

End on the wish

The last line is what this pirate wants on land: a bakery, a pardon, a bed that stays level. Put it somewhere small in the drawing, as a sketch pinned in a hammock or a seed packet in a pocket, and the character has a reason to come home.

The Known by line is your silhouette. Draw that coat, tattoo or ship's cat before the face.
Read the rule beside the story they still tell, and decide which came first.
Running a game at a table? Print 30 and let each player swap one line with a shipmate.

Questions and answers

What makes a good pirate backstory?

A way to sea, a job aboard and something waiting on land. This page deals those and three more, each short enough to draw. The berth says what their hands do all day, and the wish says why they might stop.

Are the ships and jobs real?

Yes. Sloop, schooner, brig, barque, quartermaster, boatswain, cooper and the rest are real vessel types and real shipboard posts, checked against Wikipedia. Pirate crews really did vote and share by written articles. The people, cargoes and stories are invented.

Is it suitable for children?

It was written for them. No ship is attacked in any list, and there are no weapons in use, no drink and no cruelty. The worst that happens is a week of sneezing in a cargo of pepper.

Can I use a result in my own story or game?

Yes. The lines are plain English and name no game, book or film, so a result fits any sea you have invented. Change a line, keep the rest, and the pirate is yours.