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, 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, Skiff is taking Sir Topham Hatt and the grand childrens to tour around the sea at Arlesburgh Harbour when he's saw a mermaid in the sea and Sir Topham Hatt accidentally to use anchor and roll into the sea. When they ended up in the sea, Harold and Captain come to rescue Sir Topham Hatt and Skiff and they returned safety to Arlesburgh Harbour. Skiff realise that the mermaid was only a statue.
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 is based on an Eastport Pram with an added railway chassis for travelling on the rails.
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 red, and his sail is white with yellow stripes.
- Jamie Campbell Bower (UK/US)
- Takayuki Kawasugi (Japan)
- Carlos Íñigo (Latin America; Sodor's Legend of the Lost Treasure - twentieh season)
- Patrick Bach (Germany)
- Yannick Blivet (France and French speaking Canada)
- Jakub Szydłowski (Poland)
- Gilan Shachaf (Israel)
- Jip Bartels (The Netherlands)
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.
- In the 2016 version of the Australian television program, "The Chaser's Election Desk", 4 Wooden Railway toys of Skiff appear in a skit about Australian politician, Peter Dutton, about how he talks about "stopping the boats".
- Skiff and Flynn (and possibly Terence) are the only multi-terrain vehicles in the franchise.
- Concept art of Skiff reveals that the sign saying "Skiff's Railboat Tours" on his side originally said "Skiff's Railroad Tours".
- 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)