For the large majority of our trips, my DDs are involved in the planning. I did one surprise trip in September 2014, which turned into a bit of a problem, but it worked out okay in the end. My older DD had a long weekend off of school, so at the last minute, I decided to book a trip at BC. When she asked on Thursday night where she'd be spending Friday (backup daycare, friend's house, etc.), I said "Actually, you'll be spending it with me at WDW." She thought I was joking for the first five minutes, but once she realized, I was serious, she got so excited. So, the next morning we get to the airport to board our plane, and it turns out that every flight was grounded due to some disgruntled worker setting a fire at the radar center. We spent the entire day at the airport and never got a flight out. Our surprise trip almost ended up as no trip at all. Luckily, I was finally able to get us on a flight out the following morning. I ended up pulling her out of school to make up for the lost vacation day. We had a great trip after that rocky start.
Now, I'm ready to try the surprise thing again. We have a stay planned for Labor Day at Poly, and the girls know all about that and are super-excited, as it's our first time at Poly and we're doing
MNSSHP and the AK Night Safari party for DVC members. What they don't know is that I booked us a stay at YC for 4th of July. I really want to do new Soarin' and FEA, and we only have one EP day planned in Sept, so I am worried about getting all the EP FPs I need. We decided to make 4th of July all about EP and SAB. We do have reservations on the 3rd for Narcoosee's so that we can see the MK fireworks, but that's it. Three days at EP (maybe HS for the new SW fireworks), swimming, and that's it.
I booked this trip 71 days out, so that helps with not having to keep a secret for too long. We haven't decided how we're going to surprise them yet. We certainly won't be able to surprise them once we get near the airport. So, we'll probably tell them the night before, since that's the only way we'll get them out of bed early enough to catch our flight.