We're gluten free due to celiac (my daughters) and gluten intolerance (DH and me, especially since going completely GF in support of the kids). DH and I aren't super sensitive to cross-contamination, thankfully-- shared equipment or fryers have not been much of a problem for us, so that makes it easier. During our couples trip in Sept. 16, detailed in my trip report link in my signature, we had pretty good luck with the whole GF thing.
Mickey waffles at Plaza Inn character breakfast were good; they also had muffins.
Jolly Holiday bakery has flourless chocolate cake (really just seemed like brownies, but they were good).
I don't know if it's still the case, but Blue Bayou was willing and able to make a GF version of the Monte Cristo for me. I emailed ahead and asked and they said they could accommodate. It was pretty good. I think they used a GF hot dog bun, which made for a weird shape. Also, BB had really nice dinner rolls, brown bread rolls.
Also, re: rolls, we had such a mixed bag even at the nicest places. Get this, we managed to get in for lunch at Club 33, and the "garlic bread" was prettied-up hamburger buns, buttered, herbed and toasted. Same for Carthay Circle. Napa Rose does a gf flatbread that is very good.
World of Color dessert party will do a special plate for you. We forgot to order it ahead of time, bu they still rustled up some extra plates of GF goodies for us.
Almost everywhere, dessert options were limited to sorbet or creme brulee.
Every place we went had some options, esp. table service places. They were attentive to our needs, and mostly quite knowledgeable.
For pictures and lots of descriptions of our GF struggles, my birthday trip report has lots of info.
