I have never used the dining plan at Disney World, but instead usually pay out of pocket. I also never pay off my trip ahead of time, but rather as I go, though I do make my ADRs in advance. However, I am considering a trip in December of 2015, and would like to hopefully get free dining and pay off the trip ahead of time for once. I have a few questions though. Is free dining typically offered for check-in dates for the first half of December? Right now I'm looking at a check-in date of December 13, 2015 and a check-out date of December 22, 2015 (10 days, 9 nights), is it likely that free dining will be offered then? If so, can I book that time period early and then add the dining plan on my reservation the day it becomes available? When is the earliest I can book a trip for 2015? I know the dates/prices aren't listed for booking yet on the Disney site. Which resorts are best to book if I'm anticipating free dining? I'm wanting a moderate resort, and would prefer Port Orleans, but I know it may not be on the dining plan. Is Coronado Springs much better than Caribbean Beach? Since I've never booked and paid off a trip ahead, when is usually the last point in time that I could cancel the trip and get the money back if necessary? Thanks in advance for the help. Any comments/advice for a free dining newbie would be appreciated!