This is a long term project subject to change depending on new deeds and terrain but this is basically the plan. It goes from Weeping Waters to south of Noobsdontdie in seven stages more or less. Sorry but I don't know how to make the picture bigger.
Approved with a couple exceptions. Part of phase 4 and all of phase 5 is being actively worked by Shishushu and the Edge Alliance so they will likely have that part done before you get close to that stage. So going to approve all but the parts that they will have covered before you get there. You can see there plan posted. Shishushu posted after you but has already put down a few hundred tiles headed towards those stages.
Okie dokie artichokie. Going over that mountain pass is going to take a bit of time plus there will be a bridge or bridges to be built over the straights in the south. The water there is very shallow. Maybe too shallow for even a row boat but I'll fix it so the bridges will be high enough for ships to sail under if some enterprising individual feels like dredging.