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Word crawl/Pirate Adventure Crawl

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The Pirate Adventure Crawl

Avast ye scurvy scalawag! Are ye hankerin’ for adventure on the high seas? Do ye dream of buried treasure and golden doubloons? Are ye in desperate need of a word count boost? Well, ye’ve made port at the right place, matey!

Pirate lingo aside, I’ve really enjoyed crawls this year. I know we’re almost at the end of this year’s event, but I decided to try my hand at writing one anyway. This is my first try, so I hope it's helpful. It’s on the (really) long side, so feel free to do only some of it or break it up into a few sessions, or try and finish in one sitting if you‘re really feeling brave. Enjoy!


1.) You can use a piece of eight to buy your way out of a challenge. You’ll find these along the way, along with other items that may or may not come in handy later on.

2.) Dice used is a standard six sided one. If you don’t have any actual dice, you can use this digital one.

3.) You can redo any challenge if you’re not happy with the results.

4.) Have fun!

5.) If you like, share your progress in the comments!

Part 1 - Casting Off

You find yourself sitting in an old, ramshackle tavern. The air is thick with the smoky stench of tobacco and the slightly sour smell of old rum. Music and drunken shanties mingle with the sounds of clinking dishes and rough voices. Through the window, a breeze rolling in off the ocean fills your senses with the smell of the endless blue and wakens your lust for adventure. You feel something folded in your pocket and you remember- you have a treasure map! Where you got it and the events that got you here are a bit fuzzy in your memory, but what matters now is that you’re sitting at a table with three different pirate captains. All three of them have invited you to join their crew and lend your map to their pursuit of treasure. You need a ship and a crew if you’re going to get any of that gold at all. You know you must make a choice.

CHALLENGE: They’re all trying to convince you why you should join them. Do a 5 minute word war while you listen to their words.

To your left is a wizened old coat with a gray beard and an eye patch. He grins a near toothless grin. He is Captain Christopher “Cuttlefish” Anderson. He smells and looks as though he hasn’t bathed in a year. His ship is called The Black Shark. He’ll pay you three pieces of eight to join him.

Across from you is a burly Jamaican fellow with a charming smile and intelligent eyes. He’s called simply Captain Tack. He’s dressed in bright colors and has a parrot on his shoulder that constantly repeats what he says. His ship is called The Blood Seeker. He’ll pay you two pieces of eight to join him.

To the right is the only woman in the bunch, Captain Annabelle MacFanning. She looks serious and cold, a true deadly beauty with her golden hair and the flintlock pistol in her hand pointed casually in your direction. There’s a curious gleam in her blue eyes you can‘t quite identify. She’ll pay you only one piece of eight to join her.

CHALLENGE: Do a 10 minute word war. Your word count determines your result.

More than 500 words: You join the pirate of your own choice. Pick a captain and accept their payment!

500 or less: The pirates get into a fight over you. You are kidnapped by one of them while the other two are busy brawling. Roll the dice to determine who takes you. (you get only one piece of eight with any result). 1 or 2 - Christopher. 3 or 4 - Tack. 5 or 6 - Annabelle.

Your new captain hurries out of the tavern with you, hauling you into the crowded streets of the bustling port town before you can be stopped by the others. You’re pulled along, dodging carts loaded with smelly fish and drunken pirates weaving about, until you reach the docks. The sight of the many impressive ships rocking gently in the harbor fills you with a sense of excitement. Ah, the sea! You’re setting out on a true adventure!

“Alright, move your feet,” your captain commands. “Onboard, sailor!”

“Aye!” you say, and hurry up the gangplank. You hear the sound of the sails rustling in the wind and the creak of the wooden planks beneath your feet. As you step onto the ship the captain commands you to stay on deck and heads to the cabin. The busy pirate crew stops their work and looks at you curiously. Since you‘ve been left on your own with no explanation, it’s clear that it’s up to you to make nice with this group of bloodthirsty scalawags. After all, you’re going to be sailing with them on this adventure!

CHALLENGE: Write 200 words to charm the pirates with your sea shanties and your excellent jigging skills!

The quarter master, who was very impressed, walks up to you. “Welcome to the crew,” he says, “You seem like you’ve got a good head on your shoulders, but where’s your weapon? You’ll need somethin’ to fight with on this ship, popinjay. I’ve got a few spare things I can loan you, but you’ve gotta prove you can use ‘em!”

CHALLENGE: Do a 10 minute word war to show the quartermaster your fighting skills. Your word count determines your weapon!

300 words or less: You get a dagger. Small but sharp.

500 words or less: You get a pistol. Powerful but slow to reload.

More than 500 words: You get a sword - sharp and deadly

You put your new weapon in your belt and the crew cheers, welcoming you on board. You notice one man giving you a strange glare, but he slinks away without saying anything. The captain appears and gives the order to make sail, then calls you to come to the captain’s cabin. You do as you’re told. Once behind the closed door, the captain sits down and invites you to do so as well. You look around at the many riches and odd things decorating the cabin. Even a human skull is nailed to the wall. You gulp nervously. A glass of rum (the really expensive kind) is poured and pushed across the table to you by a bejeweled hand.

“Now,” says the captain, “Let’s have a look at that map, shall we, matey?”

You reach into your pocket and produce said map. Carefully you unfold the aged parchment and spread it out over the table. You’re nervous about sharing it, but the ship is already leaving the harbor. You don’t want to do anything to displease the captain and earn a keelhauling. The captain observes the tattered map closely, smiling a greedy smile as he/she traces a finger over it.

“Aye, this be a special map indeed. How did you find it?”

“Oh, you know captain,” you say, “I heard a rumor from the cousin of a friend who knows a man who romanced a woman who may or may not have had dealings with some sort of mystical sea witch. The usual sort of thing.”

The captain laughs and slaps you on the back. “Good! Now, drink! A toast! To treasure and adventure!”

CHALLENGE: You raise your glass. The rum is rich and heady and it burns in your belly. The captain pours you another, and another, too excited about the treasure to horde the costly spirits. Roll the dice to determine how many shots of rum you get. Multiply the number x 100 and write that many words.

This drink is extremely strong and you find yourself growing drowsy right away… and then the world fades away. As the ship rolls over the waves, you roll into darkness.

PART 2- Part of the Crew

CHALLENGE: Had a little more than you could handle, aye? Do a twenty minute word war while you sleep off that exotic old spice!

If you’re sailing with Christopher, you wake up cold in the brig, in only your skivvies, without your weapon or your map. Punishment for drunkenness on duty, the captain claims. You must use all your pieces of eight to convince him to let you free. Sprint for 15 more minutes to get yourself back on deck, deal with the teasing of the crew and your horrible headache while you try to find your clothes and weapon.

If you’re sailing with Tack, you wake up right where you fell asleep- in a puddle of your own drool on the captain’s table. He’s nowhere to be seen. Be grateful Cap’n Tack found it funny and let you keep your map and your dignity. Sprint for 10 minutes to clean up and leave.

If you’re sailing with Annabelle, you wake up warm and cozy in a gently-swinging hammock in the crew’s quarters. You’re fully dressed with your map and money. She must be a bit nicer than she looked. Sprint for 5 minutes to climb up to the deck and see what’s happening.

When you get to the main deck you find utter chaos! An enemy ship is drawing near, and the cannons are firing! You jump out of the way just in time; a cannon rips through a stack of barrels, shattering them with a loud bang. As splinters fall over you and the crew scurries around in action, you know you must do something helpful! You see a pirate thrown back by a blast. The cannon he was firing is now unmanned. Take charge of it and fire!

CHALLENGE: Roll the dice to find out how many cannon balls you fire at the enemy ship! Multiply your result x 100 and write that many words to hit your mark! Go! Go! Go!

Despite your valiant efforts, the enemy ship draws up to the your ship‘s port side! Enemy pirates are swinging over onto the deck and into the rigging above your head! They brandish blades and guns and ugly scowls. You’re going to have to fight!

CHALLENGE: Time to do battle!

If you have a dagger you have a difficult time. Sprint for 20 minutes to take down a few rogue pirates but get several wounds in the process and lose a piece of eight.

If you have a pistol you’re able to hide behind some crates and take out several enemies from afar without getting hurt! However, you have a limited number of shots and it takes time to reload. Sprint for 10 minutes!

If you have a sword you jump into battle and hack and slash like a mad creature! You’re covered in blood (mostly theirs) by the time you’ve finished defending your fellow crew! Sprint for 5 minutes and find a piece of eight!

The battle is over! Some of your crew mates fell in the fight, but you managed to help defeat the enemy pirates. Congratulations! You climb over with your mates to the defeated ship to see what you can plunder. Roll the dice to determine what you find!

1,2 - You find five pieces of eight!

3,4 - You find ten pieces of eight, plus a bottle of rum!

5,6- You find five pieces of eight and a strange looking bauble.

When you return to your own ship, a young man wearing a faded scarf shakes your hand. “You’ve proven yourself, mate!” he says, “You saved my life! You’re a part of the crew now!”

You’re not sure how you feel about this, but there’s no time to ponder on it. The ship needs to be cleaned and repaired so you can continue your treasure hunt. The captain gives everyone a specific task.

CHALLENGE: Roll the dice. Multiply the result x 100 and write that many words to get the vessel in ship shape.

The ship is cleaned and repaired for the rest of the journey. The dead are honored and sunken into the sea in a sailor’s burial. By this time night has fallen, and everyone on the ship is exhausted from the trying events of the day. The captain allows the crew to break out some rum and take some time to relax and rest. A few of the pirates have instruments and they begin to play music to lighten the mood. The young man from before smiles at you. “D’you know any shanties, mate?” he asks, “Sing us a song!”

CHALLENGE: Roll the dice. Your result determines the song you sing. Open the song in another tab on YouTube, let it play, and sprint for the duration of the song to show off your singing voice to your mates!

1,2 - Mermaids from the POTC On Stranger Tides soundtrack

3,4 - No Quarter by Alestorm

5,6 - Epic Pirate Music Mix

The crew loves your performance and rum is passed around. The mood is lightened, thanks to you!

If you wrote 300 words your mates give you three pieces of eight and you head to your hammock to sleep.

If you write 500 or more words one of your mates gives you a shiny jewel as thanks for the song.

If you wrote less than 300 words, you get no pieces of eight and you have to keep the late night watch in the crow’s nest. Write another 100 words to keep from falling asleep while on duty.

PART 3 - Adventure on the Island

For several days the ship sails on without much happening. There is good weather, fine wind, and the pirates are treating you like a member of the piratical family! .

CHALLENGE: Sprint for 30 minutes to get through this long journey at sea (if you have a bottle of rum, only 15 minutes).

The bloke up in the crow’s nest suddenly shouts out. “Land ho!” Everyone runs to the railing to look. An island looms dead ahead, like a large turtle shell rising out of the sea. Although it looks like any other island from where you are, you can’t help the feeling of foreboding that descends on you. There is something strange about this island… something unnatural and dangerous. Suddenly you feel as though the treasure may not be worth the risk. Dread wraps around your heart, but there’s nothing you can do now. If you don’t do your part in the treasure hunt then you won’t be getting any of the treasure. It’s your map- you’re going for it!

CHALLENGE: Write 250 words as the ship is anchored to try and relieve your nervousness. The captain and a few select crewmen climb into the longboat. You join them. As you’re rowed to shore you grasp your weapon tightly in your hand and wonder what strange things await you on this island. Write another 100 words to get to shore.

As you step out of the boat onto the white sandy beach, you look around. The beach rolls on in either direction out of sight and leads up to what looks like thick, impassable jungle. There are two visible paths leading off through the rich flora.

“Which way do we go, navigator?“ the Captain asks you, waiting impatiently. You produce the map and look closely at the aged parchment. Which path do you choose?

CHALLENGE: Do a 20 minute word war. Your word count determines your result!

Less than 600 words - You take the path on the left.

600 words or more - You take the path on the right.

“This way,” you say, and the small party heads in that direction. As you step into the jungle you instantly feel like many eyes are watching you. A shiver runs down your spine despite the hot, humid air, but you press on. You walk for a good long while, stepping over roots and cutting through thick vegetation. Insects buzz around your ears and every once in a while you imagine you feel something grabbing at you out of the green shadows. The deeper into the jungle you go, the hotter and harder to breathe the air becomes Suddenly the thick flora opens into a clearing. In the middle of it is a large pool of clear, blue water, fed by a sparkling waterfall. You see something swimming in the water. The air is lighter and you realize, with some alarm, that the path on the map leads straight into the pool.

CHALLENGE: Write 100 words as you carefully approach the edge of the water. When you get there, a beautiful mermaid appears. She smiles at you and rests her elbows on the ground at your feet.

“Do you have something for me?” she asks. “I can help you if you do.”

If you have a strange bauble or a jewel, you give it to her. Write 250 words as she tells you the direction to take to reach the treasure.

If you have nothing to give her, write 500 words as you try and convince her to help you. In the end she refuses and tells you to leave before she kills you and the others.

You leave behind the refreshing clearing and head back into the jungle. You press on for what seems like hours through the unchanging, stifling, itchy scenery. You look for landmarks along the way. You pass a crumbling statue shaped like a monkey. You see two trees that grew together in a strange shape. All the while you think you hear footsteps behind your party, but you never see anything behind you. The feeling of being watched never ceases.

Finally, as the sun is setting, you reach your destination. The map has lead you to another clearing. It looks like there was once a village here. The foundations of ruined hut-like buildings are everywhere, overgrown with briars and weeds. In the center of the overgrown clearing there is what looks like a building made completely of human bones! You shudder at this sight, but you know that is where the treasure is hidden.

“Who’s gonna look inside, Cap‘n?” someone asks. The captain smirks and looks at you silently. It’s clear that you are the one who has to look in the strange bone building. As you approach it, you and the others are suddenly accosted by dozens of strange enemies! You draw your weapon and swallow your fear- you must fight your way through if you‘re going to come out of this adventure alive!

CHALLENGE: If you took the left path, you’re fighting living, cursed pirate skeletons! Although they are terrifying, they’re relativity easy to defeat. As soon as you give them a good whack, they’re done for. Sprint for 30 minutes to defeat the skeletons!

If you took the right path, you are fighting crazed zombie monkeys! They’re small, they’re undead, they’re fast, and they’re mean! No matter how fast you are, they seem to always get the better of you. The fiendish little beasts are almost impossible to beat. Sprint for 40 minutes to kill the wicked furry buggers!

Finally you defeat all your undead enemies! You’re exhausted as you stagger to the bone building and grab the door handle (which is fashioned from a skeleton hand). Your wounds are stinging and your chest is heaving. You yank open the door; it rattles and shakes and for a moment the whole building seems like it‘s about to collapse. You tense, but when it stops shaking you step inside. It’s dark and the air smells musty and old. You’re sure that no one has been inside this place for many, many years.

“What d’you see?” one of your mates calls out. You look around and slowly your vision adjusts. The sun is setting outside and so it is quite dark. You soon see that there are three large chests. Your old feeling of excitement and adventure returns. You have found the treasure! What gold and jewels await you? What pearls and diamonds, what items of unknown riches? Of course, you know it can’t be that easy. You take a step further inside. A skull sitting in the middle of the earthen floor suddenly starts glowing! You jump back in fright as a voice startles you, booming from within the illuminated skull.

“You have come to take my ancient treasure! You made it this far, so I will grant you a chance. One of these chests holds my treasure. The other two are cursed! Choose wisely, pirate!”

CHALLENGE: This is it! This is what everything boils down to! Which treasure do you choose? Roll the dice twice. Add your results together, then multiply x 100. Write the final result!

If you succeed in under 30 minutes, choose chest 1, 2 or 3.

If it takes you longer, roll the dice to choose your chest.

1,2- Chest One. 3,4 - Chest Two. 5,6 - Chest Three.

You’ve chosen your treasure. You carefully step over the talking skull and grab the chest. It takes all of your remaining strength to drag the heavy thing out of the bone hut and into the moonlight. You collapse on top of it, completely exhausted, your brown drenched in sweat and your clothing torn and stained with blood. The adventure is over… or is it? The pirates walk up silently, excited but nervous. You tiredly raise your head and look up at the captain, who is standing over you expectantly.

“Well,” the captain says, “Open it, and let’s see what we’ve found.”

“Aye aye,” you say, and you sit back. To your surprise, there is no lock on the chest. Slowly, with hands that shake from weariness- or is it fear? - you grasp the edges of the lid. You take a deep breath, knowing that this may be the best or worst thing to ever happen to you.

You open the chest.


If you chose Chest One- Congratulations! You chose the correct chest! You behold hundreds of shiny gold doubloons, countless jewels of every color, and exotic and strange items you know are worth a fortune. There are more treasure maps wedged in amongst the treasure, and right on top is a bound leather book. That is the first thing you grab. As the crew dances and sings you flip through it. There are stories, poems, songs, knowledge that is ancient and wonderful. With this you will be able to find a hundred treasures, and write a thousand novels. A thrill of accomplishment courses through you, revitalizing your tired body. You’ve done it- you’ve gone on a pirate adventure and found the treasure! You, captain and crew return to the ship, victorious. The celebration goes on long into the night and when it’s done you’ve decided to become a permanent member of the crew. You’re a pirate, and there is more adventure ahead for you! Write 100 words to end your epic pirate tale!

If you chose Chest Two- you chose a cursed chest. When you open it you are greeted by naught but a black smoke. It swirls and seems to grow, until it surrounds you in a dark mist. You can barely see or hear. Your heart pounds, your thoughts race. All of your mates run away in fright, leaving you to your fate. A ghostly face appears in the mist.

“You dared to disturb my ancient treasure…This is a curse of Time… You must return to your arrival to this island and relive your treasure hunt over again!” Oh no! Will you go through it all again? If you any have pieces of eight you may use them to beg the greedy spirit for mercy… and then write a last 15 minute word war as you trudge back through the jungle to the ship, empty handed.

If you chose Chest Three - you chose a cursed chest. When you open it, an invisible force reaches out and wraps around your throat. You feel a horrible coldness spreading throughout your being, grasping your very soul. You try to scream but no sound passes your lips. Your mates look on in horror, but when they come near to try and help they are forced back. You hear your captain telling them to retreat, and commanding them to leave you to die. Despair fills you as you succumb to the cold and darkness.

When you wake up you find yourself lying there in the clearing. You look down. Your wounds are healed and your clothing is mended. Strangely enough, you feel stronger than you ever have before. As you get to your feet you look up to see a ghostly figure standing before you. You realize this is the crew member who looked at you strangely on the ship.

“Ye be now cursed as I am,” the ghostly pirate says, “Never dying. Because you fought so hard, ye be stronger now than before.” The figure’s mouth curves into a dark and evil smile. “The ship and the captain who abandoned you are still on the shore. If we hurry, we can catch them.”

You smile a wicked grin. You may be cursed, but you will have revenge on the captain who left you to die. Do a 10 minute word war as you fly back to the ship in your new ghostly form, and take over as the new, undead captain of the ship. A joyful future of pillaging, plundering, and terrifying other ships lies ahead for you.

The End (bout dang time!)