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And I experimented with something like this myself.

Let me guess, you rescued the Navigator BEFORE you got the ruby. This displays another flaw in the game.

What happens is that once you rescue the navigator, he will be on the part of town where you can't get to the merchant (exit from Vanderhost's castle). From there you can get to the boat builder. If you do not have the ruby at this time you have to use gate scrolls to get to the part of town with the merchant. I say "scrolls" because if you use a scroll from there, it will take you to where you last scrolled from, then you use a second scroll to get back to town.

The ruby is obtained from the original gnome you talked to at his house. His house is the opposite direction of the Portal, on the way to the lava fields.

Once you are on the merchant side of town, you can only get back to the other side by using the portal to go into the castle again. The problem is that the navigator will not come with you into the castle and when you get back to the correct side of town to get to the boat builder (boy do I wish my memory was better with names) the navigator is not there and you can not go.

There is no way to get the navigator back to the correct dock in this situation. I heard that a guy tried to take the navigator through the castle via the lava fields and it didn't work. I didn't try this.

I hope you have a save from before you rescued the navigator. If so, go to town, get the the ruby, then rescue the navigator.

I am afraid you will be starting over otherwise. Let me know if you find anything I said is wrong. If you find a way to get it to work, post it and I'll pass it on to the other message board I read.