The Flying Welshman is a mysterious ferryman that spent most of his time ferrying people between the islands Blood Island and Skull Island, organizing haunted tours and whale-watching excursions. He was later referred to as the Lost Welshman, after the lighthouse on Blood Island stopped functioning, leaving him trapped in the accursed mists.
When Guybrush needed to travel to Skull Island, he learned the story from Griswold Goodsoup. He needed a way for the Welshman to reappear. Guybrush then had to find a way to fix the lighthouse. Once that was sorted out, the Welshman would finally find his way and appear on shore. However, he refused to help him until he had a working compass. Thanks to science, Guybrush figured a way to create a simple navigational tool, thus granting him passage to Skull Island.
Once on Skull Island, the Welshman warned Guybrush not stare at the Island's head, for he feared he would tremble at its terrifying visage. As it turned out, the rock formation on top of the island looked more like a duck. The Welshman complained that the place brought him the creeps but would wait for Guybrush to return.
After his services are no longer needed, the Welshman wished Guybrush well, as he would be leaving for Scabb Island after hearing about an opening for a chef there. After he left, Guybrush realised that his makeshift compass (a magnetized needle floating in a cork in a cup of water) would only retain its magnetic properties for a short while.
It is unknown what fate befell the Welshman.
- Guybrush can give him his makeshift compass before talking to him and know his story. In that case the dialogue will be slightly different: Guybrush will consider that as a ferryman he needs a compass, to which the Welshman will boast that he has an otherworldy preternatural sense of direction and doesn't need one; but he will take it anyway, just for the sake of Guybrush's effort. Later in the dialogue he will admit that he was lost in the mists however.
- Before parting, Guybrush instructs him to find Scabb by going "north to north-east" from Blood Island. However maps of the Tri-Island Area show a different geography.
- His name is derived from The Flying Dutchman, a ghost ship cursed to travel the seas forever.
- The Welshman himself has an appearance reminiscent of the grim boatman Charon from Greek mythology, a cliche seen also in Flight of the Amazon Queen and various other video games.
- When he answers to Guybrush's comments about mist being pretty he says: "Well SURE Mist is pretty, but EGAD, is it dull." This is considered to be a jab at the Myst series of 3-D adventure games.
- When Guybrush tells the Welshman that he is not afraid to go to Skull Island, the Welshman responds in a "Yoda style", telling him "You will be. You WILL be," just as Yoda says to Luke Skywalker in Star Wars Episode 5: The Empire Strikes Back.
- The job as a chef is a reference to the previous game, in which Guybrush sabotages the chef Bernard, takes his job, and then is fired himself.