Skiff was given wheels after Thomas had his accident and discovered Captain Calles' pirate ship. He helped Sailor John and Thomas look for the treasure, thinking Sailor John would give it to the museum. When he found out that John in fact intended to keep the treasure for himself, Skiff tried to stop Sailor John, but could not do much. He saved Thomas from having dynamite thrown at him by shaking Sailor John and later purposely capsized to stop Sailor John getting away with the treasure. After Sailor John was arrested, Skiff was recovered, repainted into a white-and-blue livery, sold to Captain Joe, and started giving "Railboat Tours" around Arlesburgh Harbour.
Skiff is a feisty fun-loving little boat with a very upbeat and positive attitude, in spite of the fact that his captain, Sailor John, is not very nice to him. Sailor John bosses Skiff about, but no matter how loud he shouts or how hard he stomps on his deck, it never seems to dampen Skiff's spirit. Skiff remains keen to make up again, and genuinely thinks of Sailor John as his friend. Skiff treats every day as an exciting new adventure; he likes to see the best in everyone and think of the world as a wonderful place. This leaves him vulnerable to persuasion to the point of appearing gullible.
Skiff's hull is painted white, while his mast and woodworkings are stained brown and his wheels rusted. In his Railboat Tours livery, his woodworkings are painted blue, his wheels are red, and his sail is white with yellow stripes.
- Skiff's name comes from a small watercraft that can carry a small crew, normally one person.
- The inspiration for Skiff came from the Ffestiniog Railway's rail-driven boat, "Spooner's Boat".