Wow, that's kind of a hard one. For DH and I it would be California Grill followed closely by Yachtsman. Until last year when we ate at Shulas, which I liked a lot, but DH LOVED it. But I would say CA Grill is the one we will always do. I just love the atmosphere. This year I am subsituting Jiko and LeCellier for Yachtsman and Shulas. I think DH is going to be disappointed at first, but I'm hoping once we try them he will be pleased. I've read such great things about both.
For DD though I would say it was probaby Chef Mickey's or 1900 Park Fare Cinderella dinner. She loved both of those. And we will try to do Chef Mickey's every time. (For the kid in me its my favorite) But this year we are doing lunch at the Castle instead of 1900 PF. So we'll see. I'm guessing that will top 1900 in DD's eyes.