C.T.
I started giving milk in a sippy at one, too. Both my kids loved milk. I began by taking away the least important bottle and replacing it with a sippy of milk. I think it was the bottle with breakfast(rice or some other cereal). After a week or so of that, I replaced another bottle and continued until only the night bottle remained. Both my children transitioned easily. Now the night bottle was a different story. I never pushed them to give it up. My oldest let us give him a sippy with milk at night around 2, but my youngest will not go for it and he's 3. I really see no difference in drinking milk at night from a bottle or sippy. It's really about the same thing to me. I know my little one won't be having a bottle when he's in high school so I'm not concerned about it at all. He can have his nightly bottle until he's 12 if he wants to. Just my opinion. Good luck!