We were planning a December trip for the kids when they were 5 and 12. They were in on all the planning and helped picked activities and restaurants etc. What they didn't know was that we were actually going much sooner (August). About 3 days before the trip we told them at dinner and it could not have gone better. Seriously. I wish I had filmed it because it could have been a commercial. They were speechless at first.. literally with their mouths hanging open, then jumping and screaming and hugging. My youngest started to cry because he was so happy and decided he needed to put himself in his room to calm down
3 days before was perfect so they had a few days to adjust, and we had been on one trip so they knew what to expect and were very excited. It was wonderful.
Now we are planning a Christmas trip (the week before) and surprising them again. They have been 8 times at this point and never want to go anywhere else. I don't expect as much of a reaction as the last time we surprised them but they will still be thrilled.
Every year when we decorate the tree I bring out a small box for each of them to open with a new ornament for the year. This years ornament will be a glass Mickey ear ornament. On it, it will say "XXX's Surprise Christmas Trip!! with the dates of the trip. Again we will do this about a week beforehand, this will give them a week to adjust and tell their friends etc.
I'll have the ornaments made on our summer trip at the Christmas store in downtown Disney. That trip is mostly an offsite trip.
They aren't expecting it and I know they'll love it.
Geez.. I forgot to answer the question! The first surprise trip we stayed at Port Orleans Riverside. This Christmas we are staying at Wilderness Lodge.