J.D.
you could try the Nuby Sippy cups... they have a soft silicone spout like a bottle shaped like a sippy.
before I tried this for my older daughter, I didn't think there was much of a difference... but she would NOT drink her milk from a sippy cup, and she switched to the NUBY no problem!
then, 2 months later, she kept biting holes in the spouts, so I switched her to a regular sippy then, and again, no problem. I think it really helped with the transition!
hope this helps!