re: Disney Pros, is it worth it to stay on site?

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How do those work exactly. I went to Disney several times as a kid, but was never "in charge"

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You should be able to schedule them now. Whoever is in charge of the planning/scheduling should know about "My Disney Experience" which is disney's website where you can manage your plans and your wristbands. There, you can plan your meals, link them along with your hotel stay, and your fastpasses. All of these will be to your wristband which has a sensor you use to get in the fastpass line instead of the "long wait" line, get into your room, and to charge meals to your meal plan.

For the fastpass, you schedule a time, a one-hour window, where you will show up at the ride and be allowed to get in a shorter line. You can schedule 3 of these per day ahead of time and add more if they are available in the park once you use them up.