Book 5 as Kian.
This is missable and should also be combined with the Never Forget Achievement.
Leave the Rooster and Kitten as Kian. Head left at the fountain into City Green. After a cutscene you find crow
. Talk to crow to update goals.
Now to the left of crow is a flagon. Pick it up.
To the right of crow is a birdbath next to pumpkins. Use the flagon in the birdbath then drink.
Right near the pumpkins is a wine merchant. Talk to him and ask to taste some wine choose any variety other then dragons for.
Pick up the thimble and drink the wine.
Now tell the merchant you want another taster.
this time choose the dragons fire Liqour drink this and both achievements will unlock.