Yeah no, getting there sounds like a good plan!
As for when they reach the city I'm not too sure, I was thinking of having someone kidnap Chance or Nessa since they probably both stand out- But I would rather for when, or if, Haki gets back to the group.
I like the idea of a wine festival! A good way for everyone to learn more about each other and have nice time before a strange tournament, maybe something along the line of "Get this magical item from this dangerous place and you can meet this powerful Mage!" And it could be an avatar of the Lich?