In '08 I went with my mom, brother, SIL and two nephews.
I had arranged it so my SIL thought we were going back to the pool one afternoon but took her to the Ritz for a massage.
The next morning, I got my brother out of bed early and we went for a ride along at the race track.
I surprised my nephews with a trip to SeaWorld which gave my brother and SIL a day and a romantic dinner together.
I babysat one night so my mom could go out to dinner with them too. Naturally the youngest got really sick and my SIL ended up coming back to the room to care for him. My oldest nephew was sooooo good that night (really the big brother and helping me out) that once my SIL got back I told him he was getting a special present even thought it was late. He's a huge Star Wars fan so I took him to DTD and we made light sabers!
The night before we left I took my mom out to dinner and to see Cirque.
This last January I went with a friend/coworker. I usually rent points and stay at OKW because I always thought I needed a kitchen (food allergy). We were getting a 1 bedroom and we were both a bit nervous about sharing space - we were going to split the time (half on the sofa bed/half in the bedroom) but I got a two bedroom and paid the difference. The look on her face when they were checking us in and confirming a 2-bedroom. She started saying, "No that's not right." and then saw my grin. I also got her ears with her name.
Now I'm surprising my mom with a trip later this year. Its been challenging saving for this one because we're moving into a new house in October. I'm getting the mortgage so my finances are an open book. My brother and SIL are "hiding" the savings I've accumulated.
My mom loves loves Christmas - all aspects. And I'm Scrooge. So she suspects nothing! On Thanksgiving, four days before we leave I'm going to give her hints with little "That for which I'm grateful" notes in our new home - alluding to the best place on earth to celebrate the holiday.
I'm not going to give her too many details about the trip. We're staying at CR and AKL (because I CAN trust Disney with my food). We're touring resorts, going to
MVMCP, the CP and the Osborne Lights - even the Yuletide tour - I'm gonna Christmas her butt until reindeer fly out of it.