i planned my brother's proposal to his fiancee at the mk two years ago (they've had a long engagement and are getting married this october - i may also be planning a disney honeymoon for them!). my brother wanted to do it at disney but didn't know what to do. his fiancee does not love being the center of attention. he wanted something really simple. i snagged a very early ADR at crystal palace the morning of (it was the 3rd day of our vacation, our second day at mk). when we got to main street, it was basically empty. i'm a huge fan of disney and crystal palace is my fave restaurant for breakfast, and she knew that from other trips together - wasn't suspicious at all by this time in the trip. also, re: finding the ring, we had separate rooms and kept it in our safe until the morning of. i then passed it to my brother when we were walking to the car.
of course there was a photo pass guy by the hub. we had a couple of pictures taken together, the four of us, then dh and i had a few pictures taken. when we swapped, i stood next to the photo pass cm 'to take pictures' and whispered to him 'engagement'. he caught right on and posed them once, then started continuously snapping. we ended up with about 50 photos of the two of them, but he caught so many awesome, un-posed shots dead center with the castle in the background. she was surprised because she expected it the first day. when we got to crystal palace, the table was decorated with a couple of balloons and confetti - i had noted it on the reservation.
funny side story, the night before we were at 1900 park faire for a character dinner. the stepsisters thought we were all pirates because we are all tattooed. when they discovered dh and i were married, they started messing with my brother and his fiancee about when they were getting married and if the stepsisters would be invited to their 'pirate wedding'. anastasia kept coming back to see if he'd asked her yet and then dragged the prince and lady tremaine over to tell them about it. if my brother was going to propose that night, it couldn't have been planned better lol. as it was, since he didn't propose, it threw my future-sis-in-law off.