I would have to say my second trip to the Anime Central convention in Chicago. Not so much for one specific reason as it was for the entire vaction going fairly smooth. We had a great suite right across the the street from the convention hall. The drive went well. Detroit to Chicago is about five hours (if you mostly obey the speed limit, at least), but of the three times I've driven to this convention, the second was the only time I didn't run into ungodly traffic. And to top it off, the Spoony Bards were playing all day in the Hilton lounge. They do some really good video game covers, and you'll see memebers switching out all day if they get a good spot. Their concert was also pretty awesome.
If you could meet any one person you wish, real or fictional, who would it be?