A.B.
I really liked Wendy K.'s answer! Maybe you could give him a budget and have him plan the vacation and make all the arrangements. That way he can see just how much work it really is to make flight and hotel reservations and rental car and activites and food and everything else. If the point of the vacation is to find something that HE likes, then let him do it. My friend's mom got sick of her complaining while on vacations, so when she was 15, she got to plan the whole thing. After she realized how much work it was and what all really went into planning a vacation, she appreciated the things that her parents had planned while growing up.