My son didn't get the point of a sippy cup unless there was something yummy in it. He would put his mouth on it, but nothing happened, so what was the point? He needed juice for constipation from 2 months old, so I finally put his watered-down juice in there, dipped the tip in straight juice, and stuck it in his mouth. His sucking instincts took over as he tried to get the sweet into his mouth, and from then on he started figuring it out. But now at four years old, he still rarely drinks water at all. I've started diluting his juice 1/3 juice to 2/3 water so he won't get all those calories. You get used to the dilution--I decided to cut my calories that way, too and now full-strength juice tastes like juice concentrate!
I know what you mean about wanting a little more freedom. I felt like a beverage dispenser. Unfortunately, my son just decided he was grown up (that's just part of his personality) and ditched me at 11 months. He refused anything but his sippy cup. It was a little bit sad. I wanted to nurse longer. So don't try to rush it. You never get this time back!