We measured in the beginning to match his bottles before he was weaned from bottles, but now that we are on sippy cups, he gets 2/3 of a sippy full with each main meal. With snacks, he gets water.
After DD turned one I gave her whole milk for lunch and formula for her morning and evening meals for a week. Then the next week I gave her whole milk for breakfast and lunch. After that she was completely on whole milk. I didn't stop measuring but after awhile I started eyeballing it. She drinks anywhere between 6-8 ounces 2-3 times a day. Sometimes she skips milk with her lunch if she's not really hungry.
Although he drinks water in sippies all day long, he absolutely refuses to drink milk from one, so he drinks it in bottles. He gets between 26-28oz a day.
My pedi said that DS could have 16-24 oz of milk a day. We found that we had to limit him to 16 oz because he wouldn't eat solids otherwise. His sippy cups are all 8 or 9 oz, so we just estimate how much milk we're pouring in there--it's not exact, but it's close enough.
I do try to keep track. At the beginning I was measuring because I wanted to make sure she was getting the minimum recommended amount. Now, I try to track to make sure she isn't overdoing it. Not a real huge concern since she doesn't get juice yet and still eats well at meals.
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Re: When your DC switches to whole milk....
Mine's still drinking the same amount of milk as she did formula (three 8 ounce bottles)