I think you first have to make up your mind what kind of trip you want. If it's theme parks, we can break down the pros/cons between Anaheim and Orlando. If it's big-city action, we can discuss NYC vs. Baahstin.

My take: Chicago kicks butt in October. So does Boston. So does the Twin Cities. So does New York. But that's just my bias: I love fall and I like all of those cities. I could probably have fun just about anywhere in Big Ten country or the Northeast in the fall. Might play golf, might run a marathon, might hit a football game, might just drink wine and watch the leaves.

I wouldn't be caught dead at Disney, although I could maybe be talked into one of those big Ohio theme parks, as I hear they make Disney look completely chumpy. But again, all you're getting here is my non-theme-park bias... I appreciate a killer roller coaster as much as the next guy, but I'll never build a trip around one.