Skiff is a small sailboat with an additional railway chassis, who used to work for Sailor John. After being abused by Sailor John for a long time, Skiff was rescued, and now gives rides to visitors around Arlesburgh Harbour.
Skiff was owned and used by Sailor John for many years, and sailed up and down the coast of Arlesburgh in search for Captain Calles' lost treasure. Unfortunately, Skiff was abused and mistreated by Sailor John, and was hit on many occasions or had his face kicked into the water.
Skiff was present near the coast of the construction site when Thomas fell into the cavern and discovered the pirate ship inside. After the discovery of the ship, Sailor John gave Skiff a removable railway chassis so that they could look for the treasure on land. Skiff met Thomas when the tank engine was eavesdropping on him and Sailor John, and he got along with Thomas quite well, telling him all about how he wished that he could be a railway engine like him.
Skiff worked for Sailor John and Thomas as they searched for the old pirate treasure, but when they could not find it, Sailor John turned against Thomas and confronted him alongside Skiff at the coastal cliffs. Skiff was surprised to find out that Sailor John was not giving the treasure to the museum as he had told him he would, but was going to keep it for himself. When Thomas shoved Skiff and Sailor John aside and carried on with his work, Skiff apologized to him.
That night, Sailor John arrived at Knapford and destroyed the Fat Controller's office, stealing the treasure chest and escaping on Skiff, despite Skiff's protests. In order to escape from Thomas, Sailor John rigged the pirate ship as an escape vehicle and fastened Skiff to it, much to Skiff's horror. As they headed into Arlesburgh, Skiff managed to save Thomas from being blown up after he shook Sailor John and made him lose his aim with the dynamite, then encouraged Thomas to derail him. Unfortunately, Thomas hit Skiff over the points and onto another track, but noticed that his line crossed over onto Skiff's and ran into him at the crossing, but this resulted in Thomas landing in the sea and Skiff sailing away. Skiff tried to tell Sailor John to help Thomas, but he was only kicked in the face and was threatened to be turned into driftwood. Suddenly, a huge wave capsized Skiff, defeating Sailor John once and for all. After Sailor John was arrested by the police, Skiff was rescued and repainted, and the Fat Controller had him give out rides at Arlesburgh Harbour. (TVS; Sodor's Legend of the Lost Treasure)
Skiff is based on the Eastport Pram, a small type of sailboat which has proven to be one of the most popular small dinghies in the world, with over 800 of them built. He is fitted with an additional railway chassis given to him by Sailor John, which runs on standard gauge railway lines. Skiff can swivel around a full 360° on this chassis, and can also be detached from the chassis via a special mechanism hidden under the water at Arlesburgh Harbour.
Skiff was originally painted white, while his woodworkings and mast were left a stain brown. His railway chassis was brown and covered in rust, and he carried a plain white sail. After he became a tourboat at Arlesburgh Harbour, his woodworkings were repainted blue, his chassis became grey with red wheels, and his sail had white and yellow stripes.
- Joe Mills originally listed Skiff as one of the characters he would be voicing in Sodor's Legend of the Lost Treasure on his website, but it was later removed. Jamie Campbell Bower was later cast for the role.
- The inspiration for Skiff came from the Ffestiniog Railway's "Spooner's Boat", a small, narrow gauge sailboat that is powered by the wind.
- Skiff's name is a word which refers to a small boat that can carry only a few people, usually just one person.