Looking for experienced parent reviews

Go as soon as you can.
My DS1 first trip he was 5 and remembers with pictures. MY DS2 first trip he was 2 (no memory); 4 next trip and remembers without pictures. DD1: 6mos first trip (soooo easy); she remembers her 3rd trip when she was 7. DD2: was 6 last time we went and barely remembers.

All that to say: We went. They LOVED it! They know its their favorite spot and it was magical for them. As for what age is best. EVERY KID IS DIFFERENT! :)

Good luck :)
 
I say go both times:thumbsup2 in all honesty I never thought the diapers/strollers were a hassle, go sooner at least you'll be in Disney sooner :)
 
I am not going to offer a nasty reply, but I just wanted to offer an opposite perspective to this for the OP. We took our first at 17 months and had a great time. I didn't find the stroller or diaper routine to be a hassle, and even though he didn't understand the storylines and wasn't tall enough to ride the thrill rides, we still had a fabulous time. He especially loved all of the characters, the Seas at Epcot, and the snow at the Christmas party, but he enjoyed everything else as well. So I am of the mindset that earlier is better, especially because your 2.5 yo is free at Disney. I have been going to Disney since I was a child, and this was probably my favorite trip.

That's how I felt as well. My daughter was just shy of two and I'm so glad we went then because she was in diapers! It was easier to deal with that then getting my four year old to the bathroom when necessary. I also liked having the stroller for all our stuff. I can't imagine going without one it made packing food and rain gear so much easier. We also have no family members who would watch our children for a full week so going as a family is a no brainer for us.
 


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