We have been trying whole milk in sippy for a week. DD takes two good drinks and then either refuses or drinks and lets it run out of her mouth. She does this with formula in sippys but loves water in sippys so its not that she doesn't know how to use them.
I'm thinking of just getting rid of bottles and formula this weekend, but I didn't know if that was too harsh.
Re: Anyone go cold turkey with sippy/milk.
I had the same problem with milk and sippies at first. I finally did just take away all the bottles (except bedtime). I think that he just wasn't thirsty enough for milk in sippies at meals if he was getting bottles too. For a few days, he didn't drink much milk, but he eventually got better at it. He still doesn't drink a ton of milk (probably about 10 oz. per day from the sippy), but I think it helped him eat solid foods better...he's pretty much a bottomless pit for solids now, which I think is good.
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With DS, we slowly transitioned him off of bottles and formula. We dropped the 2 mid-day bottles first (no milk substitute), then with the morning and night bottle, we started diluting with milk (10% milk, 90% formula for a few days, then 20% milk, 80% formula and so on) until he was getting all whole milk in both. After that, we dropped the morning bottle and replaced it with a cup. Soon after, we decided to drop the night bottle. By this time, he was drinking out of a sippy all day and didn't even seem to mind when his evening bottle was replaced with a sippy.
We started this when he was 12 months and I finally put the bottles away at 14 months.