You just need to go to the northwestern corner.I did not know that you could travel to Free Haven from New Sorpigal by coach. IIRC I have occasionally been able to travel from Ironfist to Free Haven by coach. I guess I usually hire a Gatemaster and get Master Water early and make very little use of the stables' services. Therefore I have never really looked into how the travel schedules work.
Back on topic I second the Scholar + Instructor choice of NPCs.
I would start with Air/Water for my Sorcerors and whatever for my cleric. Magic skills have a much greater value moneywise than leather. Learning leather is cheap and you will soon enough find some suits. Learning magic skills is more expensive.
I agree that the personality of the cleric should be high, but I think I prefer Accuracy and Speed over Endurance; you are going to rely on bows for a while.