One does not Simply Sail into Movies
Two if by Sea
Three Sheets to the Wind
Stood on the Forecastle
Ask me if I've sailed
100

Tick Tock

This pirate is afraid of a ticking crocodile in Disney's "Peter Pan".

Captain Hook

100

This coin got it's name due to the fact that it was valued at twice a standard Spanish gold coin.

Doubloon

100

According to maritime lore the souls of sailors drowned at sea go to this mythological place.

Davy-Jones' Locker

100

John "Calico Jack" Rackham was a moderately successful pirate who famously sailed with two prominent female pirates. Name one of those female pirates.

Anne Bonny

and

Mary Read

100

This small open top boat used for ferrying people from the shore to vessels in open water or vise versa was traditionally propelled by oars but more often now with outboard motors.

A Dinghy

200

Hey you Guys!

This pirate, only seen on screen as a skeleton, hid the treasure the children are hunting in the movie "The Goonies".

One-Eyed-Willie

200

These are the words for left and right on a boat or ship.

Port (Left) and Starboard (Right)

Originally called Steerboard, Starboard was the side of the ship with a rudder on Viking boats, meaning the port side was the opposite side.

200

This decoration carved into the bow of a vessel is said to contain the soul of the ship itself.

The Figurehead

The USS Constitution's figure head was Hercules, until they replaced him with President Andrew Jackson. 

Weird.

200

This privateer was once the lieutenant governor of Jamaica, and now is more famous for mid-tier rum.

Sir Henry (Captain) Morgan

200

This black flag with a white skull and crossbones is associated with pirates from the Golden Age of Piracy.

The Jolly Roger.

In fact there are many Pirate flags.

300

This antagonistic pirate from "Treasure Island" also has a fast food restaurant named after him.

Long John Silver

300

This iconic piece of face fashion was said to help with night vision, and not just to cover grisly wounds.

Eyepatches!

While there is no historical evidence of this being true the theory goes that sailors would swap the eyepatch to their other eye to go below decks and that eye would already be accustomed to the dark.

Mythbusters tested this theory, and found it to be plausible.

300

This famous form of seafaring execution often depicted in movies was also how Jabba the Hutt tried to have Luke Skywalker executed, minus the sarlacc pit of course.

Walk(ing) the Plank

There is no recorded historical evidence to prove it ever actually happened only rumours.

300

This privateer turned pirate gave rise to the myth of buried pirate treasure on Oak Island, as well as islands in Maine, Connecticut, and New York.

Captain William Kidd.

Fun Fact. 

Despite his reputation Kidd never committed piracy. Years after he was executed there was a review of his trial that proved he had been framed and all the awful things he'd done were perfectly legal.

300

This system of ropes, cables, and beams allow sailors to control the sails of a boat.

The Rigging

400

As you wish!

This pirate dressed all in black was actually a series of pirates who passed down his name as a title in the book/movie "The Princess Bride"

The Dread Pirate Roberts

400

Two pirates were caught and hanged on this Halifax Harbour Island in 1784.

George's Island.

They also hanged a pirate at Black Rock Beach in Point Pleasant Park. 

Crazy.

400

Sometimes mixed up with mermaids, these mythological half-bird half-woman creatures lured sailors to their deaths by singing at them.

Sirens.

What kind of idiot falls for that? Half-bird, are you kidding me?

400

The legal name of this very famous pirate, known for tying lit fuses into his beard and having such a terrifying reputation most people surrendered to him, was Edward Teach.

Black Beard 

Apparently he was actually not particularly violent because most people surrendered based on his scare tactics. It's said that more people died during his final battle than any other in his 2 year career.

400

This structurally significant element is important for the stability of a ship/boat.

The Keel

The Danes would punish sailors by lowering them into the water at the bow of the ship with ropes tied to their hands and legs, holding the ropes on either side and walking the length of the ship dragging the person along the keel, they called it Keelhauling.

What fun!

500

Look at me, I am the Captain now.

The Maersk Alabama is the name of the ship at the centre of this 2013 movie about an act of piracy that took place in 2009.

Captain Phillips

500

This ammunition is two halves of a cannon ball connected together by a length of chain and fired at the masts and rigging of opposing ships.

Chainshot.

500

This mythical ship, often said to be crewed by ghosts, is said to fly through the air upside down.

The Flying Dutchman.

Some scholars claim sightings of the Flying Dutchman could be the result of the optical illusion known as a mirage.

500

This english privateer was captain of the 2nd circumnavigation of the earth, and was later knighted by Queen Elizabeth I.

Sir Francis Drake

500

The sailor with this title is in charge of logistics, inventory, and wages including the Captain's.

The Quartermaster

Sometimes considered to have more power and influence than even the Captain the Quartermaster made sure everyone on board was fed, had a place to sleep, was supplied with clothes, weapons and ammunition, and got paid.

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