Sorry, havent been about for a couple of days!
The first cup dd got on with was the tommee tippee first cup - it has a flip down spout and is a freeflowing one and is widely available in the supermarket, chemists, mothercare, etc. (dd couldnt get water out of the other cups we tried) I always offered water with meals out of it from around 7 months - at first she would only take a couple of sips (literally) but she did improve over time - I always left the cup on the highchair tray so she could fiddle about with it herself too. Once she had the hang of having to suck from the spout, she was able to use the cups with valves e.g. avent magic cup, etc (I avoided the anyway-up cup though as I found it difficult to get anything out of it!!)
When I first stopped the morning bottle and offered the cup, I tried offering it in place of the bottle before breakfast but she was having non of it...lol. I therefore offered it along with breakfast instead and she took a little more. I stopped the evening bottle one night after that when she started playing about with the bottle and sprayed the milk about (that was why we ended up using the avent magic cup as it is non-spill)
Her intake did go down for a few days as she got used taking milk from a spout instead of a bottle but there wasnt any crying/moaning about it and it never affected her sleeping through either.
From 1 year the recommended intake of milk is between 12-20 ounces inclusive of milk in cooking, in cereal, dairy products, etc so they dont need to take so much milk as a drink so this was why I wasnt as worried about her milk intake after she reached that age.
Sorry for rambling!! If theres anything else you want to know, just ask