For us, the easiest ways to save on our trips were the obvious ones - we go during free dining or a major sale (we went for 40% off when we went the first time). Of course, this means going during "off season" - Jan/early Feb, and that was fine with us. We took our daughter out of school.
Here's how much we spent:
2010 - 7 days for $3,200 - including Deluxe hotel on site, PH tickets,
DDP, airfare, $300 for tips, drinks (alcohol) and souvies
2012 - 11 days for between $3,800 - $4,000 - same as before.
These are the only real "budget-y" things I did for our trip:
brought breakfast foods/snacks. I brought a box or two of pop-tarts. I never allow them at home, so they are a vacation treat in the hotel. I think DD will grow up thinking hotels come with pop-tarts
We could have also brought bagels, as our hotel had cream cheese out every morning in the QS dining area with the condiments. We could have also brought bread and made toast, as they also had butter and jelly out.
Shared QS meals. We are not huge eaters, and meals at DW are huge. We usually split 2 QS meals between the three of us. One of us would take DD to find a table and sit and the other would order 2 adult meals and we would share them. There was usually enough that dessert would only get one or two bites to taste, or wrapped up for later. I'm a water drinker, so I'd just throw a slice of lemon in it and I was good with the 2 drinks that came with our meals. This gave us a surplus of QS meals, and in the later days of the vacation, we'd say yes to our urges for "midnight" snacks when we got back from the parks or before going back to our room after the EWP.
did laundry at our hotel halfway through vacation. This saved on luggage, which meant we didn't have to check any bags, which meant we didn't have to PAY to check any bags.
swiped out all our leftover snacks/meals at the end of vacation. We got pkgs of fruit snacks and saltwater taffy to bring back to classmates, teachers, etc. We had like 8 leftover our first trip and 13 on the last day of our last trip. It was crazy how full we were the whole time!!!
As for saving FOR the trip... I dunno. DH handles the finances, and we just decide when we are going to go. We have a bit of disposable income, so I don't worry about it too much - he generally works it into the budget. I will say though, that we live under a rather rigorous budget to begin with (similar to the envelope system) so each cent is well thought out before it gets spent. It's amazing how much we started saving when we stopped spending willy-nilly! All those tiny trips to Target and Starbucks and the boutique toy store really added up to about $200-$400/month of my random spending. Yeah, DD had a few more cute seasonal tops, but really, how many Happy Halloween shirts do you need? (one year, she had over 7 - I was out of control!) But at the time I was buying them, I was thinking "it's only $5!" yeah, but in reality, it ended up being almost $40! See what I mean - it all adds up! Oh, and after Nov 2, Halloween shirts are generally tacky. ugh, I was so dumb and wasteful!
Within my budget ($100/week for groceries, toiletries, and everyday spending like field trips, etc) I try to save each week. It's turned into a little game for me... how little can I spend this week? Each week, I start anew, and when I have about $60-$80, I either don't take the next week's allotment, or I splurge on something for myself or the family. Once, I bought a bunch of new running gear. Another time, I bought the Harry Potter BluRay set of all 8 movies. Another time, I bought Crocs for us all to wear at the pool at WDW.
