Since you asked for thoughts...here's mine.
First I don't like the thought of you using an "emergency leave" for a family vacation. I think it brings bad karma and you should remember that when your family really does have an emergency and you know you used those days to go to Disney World. Also, I would think you'd have to have a reason so what do you say? To you pretend a relative is sick or dead...not something I would ever do, personally but I know some people don't have any problem with faking emergencies to get some playtime.
My sister also works in schools and we have found fantastic deals for Disney trips that we just can't do because she can't get the time off. It sucks but her job is an important one and we will get to go to Disney again...just not at that particular time. She understands what the job entails and while there are perks (like having summers off to spend with her daughter) there are also drawbacks and this is one of them.
I think honesty is the best option. Tell your boss the trip is booked, paid in full and that you obviously had no idea there would be extra days to make up. Then you offer something to make it up whether it be to do some extra work before you go or to help out with something else. You are asking for a favour and you should be prepared to reciprocate. She doesn't trust you already for some reason so if you are not prepared with some options of how you can make it up to her she has absolutely no reason to help you or be on your side. That's how favours work, especially in work situations - you need to be prepared to give if you want to receive.
Finally I think you need to anticipate the repercussions and accept them. If you lie and go anyway and it ends up being the worst case scenario (fired with poor recommendations on your record) then that's the bed you made and you need to lie in it. Obviously that is the worst possible thing I could imagine but even something smaller like your current boss telling the boss at your new school that you are a liar and will skip work to jet off to Disney World could make your life an unpleasant one.
Of course, we all hope the best case scenario works out for you but in case it doesn't you should be prepared for the consequences however you choose to deal with this situation.
This^^ Job security is a precious thing in this crazy world. And as wonderful as Disney World is, it seems like a poor way to risk not only your current job but your reputation going forward should you want a different one. And I'm going to guess those future employers will want recommendations from your last one. Imagine that scenario for a sec if you are found out... "Yeah she is a known liar who places more importance on Disney World, something that is there 365 days a year including summer break, over her job and responsibilities to her students and fellow faculty. At the very least, she schedules her vacations during a time when there is a known possibility of make up days. Totally hire her. Not." Instant ruination of career.
And your boss sounds the type to do that! I am truly sorry your boss isn't nice. I worked as a lifeguard during my teen years and if you weren't a chosen favorite of the manager, man she made your life miserable. Obviously not quite the same as your situation but just trying to say I empathize.
I really think honesty is the best solution. You said she didn't like it, but at the same time she let you go the last time you went on a Disney trip. But you got through it, and noticeably, you are still employed. So she got through it too. And at least your boss knows you are an honest person even if she doesn't quite trust you. As she said above, come with offers of how you are going to make it up to her. Maybe offer a couple different options.
I've seen your posts and know what a sweet person you are @
bethymouse, and I won't make judgements on you whichever way you go. But I will say it again... As wonderful a place it is, Disney World is simply not worth jeopardizing your career over. This isn't like lying to just get your kids out of school. This is your career. Your reputation. The implications if you get caught could be enormous. I guess you have to decide for yourself if Disney is worth it. For me, it would not be.
**Also, I recommend telling your boss sooner rather than later, should you choose to. The sooner you tell her, the more professional you look, and the sooner you can offer to do things as a way to make up for it.
When we went September 2012, I did not lie to my boss about taking off ( I had never done this before, and will never do it again sadly). She was livid! But, I did it anyway because I had the days to take! I may have to take a day or 2 off ( June 10 & 11). The kids last day should be June 6 w/ a teacher day on the 7th. I will not be there for prep and closing ( teacher days). I will have to call it "emergency leave" and come up w/ a lie unfortunately!
