We have taken several trips with the following strategy, and it has worked well for us. If Christmas or a birthday is right before (or reward for good grades, etc.) we give each child a $50 gift card. This is used however the child likes. We also allow each child to choose how much of their own saved money to bring. Our kids only use their saved money to deposit in the bank or take on trips, so I feel comfortable giving them discretionary money. They have never chosen to bring more than $40, and they often bring money home (they know it is theirs... That toy doesn't look so appealing when they have to pay for it!) I have had a kid pick ears, toys, stuffies, key chains, even a snack! When it is gone, it is gone. I have given more guidance to the 4 year old or 5 year old (if you buy this, you will have enough left for something small, etc.), but they have never challenged it. I have 2 very different shoppers, too: boy buys something immediately, usually after seeing someone else with it. He does not step into a store again. Girl looks in every store she can and typically waits until the last day. We obviously pay for the kids' foods, and I buy them each at shirt if they want, but all other souvenirs come from their stash. We did have one trip where the middle kid's behavior was so bad, he was not able to shop. He just couldn't pull himself together to go into a store. So, the money went back into the piggy bank! Our trips have ranged from 4-6 park days. If we are combining Disney with something else, the same amount of money covers all places on the trip.