How did you wean from bottles?

So my LO still takes a bottle three times a day and doctor said its time to start weaning to a sippy cup. He will drink everything but milk out of a cup. I plan on doing a cold turkey switch to milk in sippy cups that he likes BUT my question is- do you do a sippy cup before each meal, or with each meal, or after each meal? He is offered water all day from his other sippy cups so he is plenty hydrated and has three meals and two snacks a day. When we do bedtime I give a bath and teeth brushing, a book and a bottle then I rock and place him in his crib. So he essentially goes to bed with milk teeth which I know is horrible so I’m wondering do I give a sippy with milk at dinner time or a sippy before his bath so I can brush his teeth. What are your guys milk routines looking like?

TIA!

EDIT: Baby is 14 months and I am referring to whole milk