I'm not sure when I will be comfortable with this. My oldest DS is 13, and I can't imagine him wanting to go off by himself. We have been to WDW about 13 times, and although he should be pretty familiar with the surroundings, I'm not sure that the transportation would not confuse him. You know, they don't always pay the most attention to what is going on around them! I have let him ride things in the past that his younger brother and sister could not ride and met him at the end, and I've even let he and his brother (9yo) go to a ride in the general area my daughter are in, and then meet them. We have very specific guidelines about this, so maybe if we continue to practice this and then branch out a little bit, we will all be comfortable and qualified to let them strike out on their own when the time is right.