Okay, so I have always wanted to take all of my children to Disney at once, but could never find anyone to go with us even when offering to pay their full expense. My youngest will be 4 in October and has never been, my soon to be 6 year old has been once but doesn't love it, my 9 and 7 year old's have been 5 times each and are true Disney lovers. This is the plan for the December 14-20 trip. My son's birthday is on the 19th so I wanted to be there for it, but still leave by the time things get really busy for the holidays. Also, on the Disney website if you start your vacation when free dining is still in effect they give it to you the whole trip right? It would be Me 27 Mom 71 4 DS's 8,7,6,4 (age at the time of the trip) My plan is to get two separate rooms at an All Star value resort with one adult and two kids in each room and then ask for adjoining. The room with my mom and two younger children will get an upgrade to the basic free dining and 6 day tickets. My room with the two older boys will get free dining with upgrade to basic and a one day ticket since we have seasonal passes. The one day tickets will be used on the 19th as it is a black out date for the passes and we will still want to be in the park on my son's birthday. The cost comes to $1407.52 for my mom's room $977.27 for mine. Total: $2384.89 A few question for those who have made it this far lol. 1. If we get to the resort early on check in day what are the chances that we can get adjoining rooms? 2. Will the free dining apply to our whole package as long as our vacation begins when it is still in effect. 3. Is this the cheapest way to go? Thanks in advance for any help!