How can I make the transition from bottle to sippy cup easier?

We use a brand from the dollar stare called Nuby. But it has a soft plastic spout and lid which you mentioned you didn't like. We like it because he can control the flow and drops of water come out if he sucks or bites on the spout. It worked much better for us than the hard plastic lid type did. We do let him have one in bed but so far, he doesn't drink anything but water in it ever, so I don't worry about tooth rot. He also doesn't get it unless he is actually thirsty, he doesn't use it like a pacifier and just chew on it to chew on it. mm..I don't know that I've seen any large ones with the handles either. Just the ones like an actual cup with a straw thingy in it. I don't know about going cold turkey. Our son still gets one bottle at night before we put him to bed, so he still uses both, but mainly a sippy cup.Good luck!