Story Related - Cannot be missed.
You'll be given several steps.
One by your mother to eat, then to speak to father.
Father gives you a few steps.
Get coin from a debtor (this introduces the speech challenge)
Get him a beer
Get Charcoal
Get sword guard.
The Guard should be your first point of call as all you need to do is walk to your right towards the Castle. Talk to the guards to get it.
Then try to get the money, if you're able to do it by thr challenge, great, but the more lilely outcome is a fist fight, just run away in this case and return to father, tell him what happend and he'll give you some coin.
Then go to the trader and get charcoal, you need 10.
Get the beer last from Bianca, otherwise your father will say it's too warm and you end up going back to the bar for the other.
The Trophy pops when you leave town.