Skiff is a railboat. He was originally owned by Sailor John, but now gives Railboat Tours around Arlesburgh Harbour with his new Captain Joe. He is a feisty fun-loving little boat with a very upbeat and positive attitude. 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.
- The Blistering Cold (deleted scene cameo)
- Shorts 10 (mentioned)
- Before getting fixed up, he was painted brown.
- 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".