Hi. We did 10 nights with the dining plan with three kids, the youngest being 31 months at the time. He really did alot better than I expected. Granted, we took him out to dinner many times here at home so he was not new to the behavior we expected of him in restaurants. But I was surprised that we had so few problems. If you come prepared, it is doable for sure. We did a number of character meals which provided good distractions. Buffets can be good with 2 yr. olds because of the variety of foods available. Just come prepared with a variety of little toys. We found a bunch of small animals that were a hit with the 2yr. old and the 5 year old, and did not take up much space. We also brought along some crayola wonder markers and paper. They only write on their paper. I had not let my 2 yr. old color with markers before so they helped a bunch in restaurants and on the plane. Oh, and don't forget that you don't have to use your TS meals for supper. You could book some of them at lunch time if your 2yr. old might be happier then. If you do book them for supper, just remember that the later time you book, the more tired your 2 yr. old may be. We tried to book our meals between 5 and 6 for that reason. Oh, one more idea. We have taken a small container of playdoh with us to restaurants before (not to disney though) and it kept him quite happy till the food came. Good luck!