R has no problem drinking from a cup at the table. However I still find myself giving a sippy, even with meals. He usually doesn't finish the drink, so I end up using a second cup anyway so he can walk around with the drink.
I have a cupboard FULL of sippies....way too many but I can't break the sippy cycle! lol I bring him a sippy of milk every morning when he wakes for the day, then he has his juice with breakfast. When that is gone I refill with water and he can sip on it until lunch. We also always let him have a sippy of water in the car. I do have a couple of spill resistant ( we all know NOTHING is spill proof) water bottles, maybe I should try those for awhile and only give the sippy in the a.m.?
Does your toddler still use the sippy mainly, or do you have your cupboard space back?
Re: When to ditch the sippy?
I'm in the same boat. I've been giving him a cup at the table w/ his meals, but I definitely don't trust him to have it if he's sitting at his little picnic table in the living room (where he sometimes eats breakfast, and always eats snacks)
Since he's started DC, they only drink from cups so he's gotten really good at not spilling. But I can see a cup sitting on the coffee table and a toy getting thrown at it and spilling milk/juice/water everywhere!