Emma, our recently turned three year old, had been drinking her milk out of bottles since I weaned her from breastfeeding at the age of 11 months. She used sippy cups and regular cups for other drinks, but white (plain) milk had to come out of the nipple of a bottle. I am the type of person who never expected to let any of her kids drink out a bottle past age one. But, as other ideas and principles change after you have your own kids, I allowed Emma to keep drinking milk out of the bottles after she was one.
At about 17 months we attempted to take the bottles away, but it was a hellish experience. Emma completely stopped drinking milk for the time we took the bottles away (about three days, I think) and was extremely whiny. I was seven months pregnant with Zoe and just felt a lot of anxiety over doing this, so I gave in and gave Emma the bottles back. We did scale back the amount she drank and number of times she could have the bottle, in hopes of making the eventual transition easier and because she ate more food when she wasn't drinking so much milk.
Well, as the months passed and her third birthday was approaching, my husband, Brendan, told her that when she turned three she couldn't use the bottles anymore. Her third birthday was on Friday, and she has not had a bottle of milk since. When Brendan left for work on Friday, he took the bottles with him. We told Emma that he was giving them to some babies who needed them. When he left I asked Emma if she wanted to say goodbye to her bottles. She said, "Goodye bottles. Goodbye bottles. Goodbye sweet bottles." She also has only had one sip of plain milk since that day. She has special princess sippy sups that we told her she could use when she stopped using her bottles. She eagerly anticipated getting to use the special cup, but she took one sip and made a face that said, "this stuff tastes like swill." Since then, no amount of offering, coaxing, suggesting she try the milk in a regular cup or through a straw has worked. She gets one cup of juice when she wakes up in the morning and we told her if she wants any more juice throughout the day she has to drink some white milk. She refuses and drinks water instead. After her nap she drinks a large cup of chocolate milk through a straw, but no white milk.
This could be difficult.