J.L.
My husband is the one who did it with my son, and he did it at 1 year old. He was drinking out of a sippy cup all the time, except at bed time...he would take one bottle and bring it out to us (he was walking) then he would go back to his bedroom and go to bed. Finally my husband wanted to do away with the bottle scenario and handed Hunter a sippy cup one night. He didn't drink out of it, but he fell asleep cradling it. It was cute, his switch was kind of easy. I wish I had more help for you, but my daughter is 11 months and REFUSES to drink out of a sippy cup and wont drink anything other than milk, so I don't know what to tell you.