October 15/16 is the earliest I would want to do anything, since we'd like to get annual passes and get two Food and Wine trips out of them, one at the beginning of the AP year and the other at the end.
Since October 15/16 is a weekend, if that's the cruise date I'd prefer to do the cruise first. However, I won't know whether we'll want to do a cruise until we've done our upcoming September cruise and know whether or not we like cruising. We don't have a cabin preference so if we can't book until this September it won't be a problem.
Any of the following weekends (October 22/23 and 29/30, or even early November) would also work for us, but the 15/16 weekend would satisfy both us and the Colonel.