Daxx's Wife here! I surprised Daxx & DS with a Disney trip. Here's the story ... I was offered a teaching job the week before Christmas at a school I was substituting in. I accepted a teaching job a few days before Christmas in 2003 and started after Christmas break. Perfect timing for a gift of a Disney vaca.! Even though I knew I was going to take the job, when Daxx would ask if I'd made a decision, I'd start hemming and hawing about and didn't tell Daxx that I'd accepted it. That made it easy for a surprise!
I called Daxx's boss the day I accepted the job and told him of my plans. I asked him what time frame would be best to take off in the summer and he made the arrangements w/me. He was really, really good about it and said he wished his wife would do the same for him!
With Christmas a few days away, I wrapped up the key to my new classroom in one box and the Disney Vaca. Planning Video (from our July 2003 trip) in another box. I made Daxx and DS open them at the same time. They soooo didn't get it! I had to tell them that I took the job (thus the key to the classroom) and was giving them the gift of a Disney vaca. w/the money I'd be making. They were stunned. I told Daxx that I had booked everything. Of course, he said he didn't know about work vaca. and was shocked when I told him it was all taken care of w/his boss. He was floored b/c he had no idea I worked things out. He was shocked his boss kept it a secret!
In turn, for DS's bday in Oct., we surpised him w/a trip. He had NO idea -- I packed our clothes in a suitcase that was hidden under the bed in the spare bedroom. Our flight was on a Thurs. night ... so after school, I picked him up from Grandma's house and told him that we had to meet Dad at home at 5 pm b/c we had to go plan for my niece's shower and had to be at Aunt Sally's house immediately (aunt lives near the airport). But, I said "Daddy's going to be so mad b/c we have to get there but I have to stop at the teacher's store" which you drive right past the airport to get to. So, Daxx hid the suitcases in the very back of our van. We got home, hopped in the car and I told Daxx that we had to go to the teacher's store near the airport. He pretended to be exasperated, saying it would make us late for Aunt Sally's. So, as we're getting closer to the airport, we see a plane taking off and I say (as I always do when I see an airplane), "Bet they're going to Disney!" and Daxx says "Disney, Disney, Disney!" and I said "I bet you wish you were going!" and DS is in the back of the van, reading a magazine and not saying much. So, we pull into the airport area and are heading to long-term parking. DS still has his face in a magazine. It wasn't until we got to the automated ticket machine that says "Please take your ticket" that DS looks up from his magazine and says "Where are we?" and I said "I don't know -- you tell me!" and he says "The airport?" and I said yes. He asks what we're going there and I tell him (all weepy) "We're taking you to Disney for your Bday!" and DS (as any soon-to-be 8 yo) says "Yeah, right!" I said "We are!" and DS asks where the luggage is. We tell him it's in the back of the van. We parked the van and he says "So, where's the luggage?" and Daxx pulls out our luggage. DS still doesn't believe this ... even as we get our plane tickets and boarding passes. He keeps saying "So, when are we going to turn around and get back in the van?" and I tell him that you can only get through security w/plane tickets. He is still not buying it. It wasn't until we were seated on that airplane that it clicked in that he WAS going to Disney!!!! He was ecstatic and in shock!!!! It was the BEST surprise we ever carried out!! It was even better than the Christmas trip surprise b/c DS had absolutely no idea/clue/etc. that we were going. He didn't even know we had packed bags. He was asking "Did you bring ..." and we'd answer "it's packed!" We thought of everything!!!! Too funny!
Good luck. My advice ... call HR/his boss/whoever does vacations and make arrangements w/them and tell them to keep it hush-hush! It worked for me w/Daxx ... I'm sure it would work for you, too!