Skiff was given wheels after Thomas had his accident and discovered the 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.
In the twentieth season, he and Captain Joe were checking the harbour to make sure everything was safe before a storm. While Joe was busy elsewhere, Skiff's sail came loose, his anchor rope snapped, and he was blown down the line into a fallen tree, where he derailed, came loose from his chassis, and got his sail trapped under a branch. Duck and Oliver were both approaching the tree from opposite directions, but Skiff just managed to free his sail and warn them of the danger, preventing a serious accident. The following morning, Sir Topham Hatt praised Skiff and said that he deserved an award for his heroic actions. Then everyone gave Skiff three cheers.
Later on, Skiff overheard Sir Topham Hatt talking to the Museum Manager, and became convinced that a mermaid was coming to the harbour. The following morning, he was to take Sir Topham, Stephen, and Bridget Hatt on a tour. While Captain Joe was getting the children's lifejackets, Skiff saw something in the water that looked like a mermaid's tail, and took off after it with Sir Topham Hatt on board. The chase resulted in them getting marooned on the beach at Bluff's Cove, and Harold and Captain had to come and rescue them. Back at the harbour, Skiff learned that the "mermaid" was really a figurehead, which was to be attached to the bow of Captain Calles' Pirate Ship as a decoration.
Skiff is a feisty, fun-loving little boat with a very upbeat and positive attitude, in spite of the fact that his former captain, Sailor John, was not very nice to him. Sailor John bossed Skiff about, but no matter how loud he shouted or how hard he stomped on his deck, it never seemed to dampen Skiff's spirit. Skiff remains keen to make up again and genuinely thought of Sailor John as his friend, at least until John revealed his true colours. 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 is based on an Eastport Pram with an added railway chassis for travelling on the rails.
Skiff's hull was painted white, while his mast and woodworkings were stained brown and his wheels rusted. At the end of Sodor's Legend of the Lost Treasure he was repainted in a new livery; his woodworkings are now painted blue and turquoise, his wheels red, and his sail is white with yellow stripes, while his hull remains white.
- Season 20 - Blown Away, The Missing Breakdown Train, Cautious Connor (cameo), Hugo and the Airship and Skiff and the Mermaid
- Jamie Campbell Bower (UK/US; Sodor's Legend of the Lost Treasure onwards)
- Takayuki Kawasugi (Japan)
- Enzo Fortuny (Latin America)
- Patrick Bach (Germany)
- Yannick Blivet (France and French speaking Canada)
- Jakub Szydłowski (Poland)
- Gilan Shachaf (Israel)
Joe Mills originally listed Skiff as one of the characters he would voice in the US on his website prior to Bower being cast for the role.
- 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".
- In the 2016 version of the Australian television program, "The Chaser's Election Desk", 4 Wooden Railway models of Skiff appear in a skit about Australian politician, Peter Dutton, about how he talks about "stopping the boats".
- Skiff is currently the only character who can travel via both rail and water.
- Wooden Railway
- TrackMaster (original, two pack with Hugo)
- Motorized Railway (original)
- Mega Bloks (original)
- Collectible Railway
- Capsule Plarail (original and railboat tours liveries)
- Motor Road and Rail (unpowered in original (Looking for Pounding Treasure Set) and railboat tours liveries)
- Adventures (coming soon)
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