Solution, if you still need it:
The sailor lives in a cardboard house. He'll sail you across the sea if you have a ticket. Thankfully, there's a store in town that sells them. There's no one right way to get enough money to buy one! If you're struggling to afford a ticket though, you should know that there are many trashcans with money. Including one with quite a big sum south of town! It's through a cave which has a locked door, but if you poke around the buildings you should find a key to open said door without much trouble.