- “Rocky didn't find that ship. I did!”
- ―Thomas, Sodor's Legend of the Lost Treasure
Back in the sixteenth century, Captain Calles hid his ship in a cavern between Arlesburgh and Harwick in an attempt to get away from the merchants and the Navy. The entrance to the cavern collapsed, leaving the ship there to rot away.
Over four hundred years later, Thomas found the ship after falling into the cavern during the construction of the Harwick Branch Line. However, Rocky took the credit of finding the ship after he pulled it out. The ship was placed on a flatbed and Donald and Douglas took it to Arlesburgh Harbour to be put on display. The discovery of the pirate ship was the reason Sailor John converted Skiff to run on the rails; in order to search for Captain Calles' buried treasure. Sailor John later converted the ship into an escape vehicle to get away from Thomas, but the ship was pulled over thanks to Bert, Rex, Mike and Ryan.
The ship was eventually recovered and put back on display in the water at Arlesburgh Harbour while Thomas and Skiff, who would now give railboat tours, watched the fireworks in the sky.
A mermaid figurehead was added onto the ship later.
Captain Calles' ship is brown with some woodwork painted blue. Its sails are white and on top its central mast is a weathered Jolly Roger flag.
- Captain Calles' Pirate Ship is made of wood, but incredibly remained complete and undamaged for more than 400 years, while it should have rotted away long ago. It's possible it was built using Jobi Wood.
- It is currently unknown how Sailor John managed to take the ship from Arlesburgh Harbour to the hill.