Our neice is a Cast Member in Mgmt. at the world and she said that they offer the free dining plan during their slow seasons. I know when we were there in Sept. 07 we were offered the free dining as a bounce back offer however you had to book prior to checkingout. The 2008 free dining offer dates are August 30-September 27. We booked Sept. 27 through Oct. 4. As long as you booked any of the offer days you get the free dining throughout your stay. As you see, we booked the last day through Oct. 4. My husband is a teacher and retired in June so we're open to any dates now and that is SUCH a treat. Love it!
I'm not sure if the 2008 free dining dates will work for me. I teach kindergarten and cannot take days off in September. Maybe, by some miracle, Disney will decide to start free dining mid-August!
Last year it started August 22. We arrived on August 15th, so couldn't book it or have it applied to our package. I hoped it would be on our dates and it wasn't, so this year I'm not even planning on it as the window appears to get smaller each year.
It's too bad the window keeps shrinking. Does Disney really lose money during the free dining promo? Probably not! If people don't have to pay for food, they'll spend their money on other things. Hopefully Disney will increase the window of availability. Am I asking for too much?
The booking window keeps shrinking because the resort rooms are filling up anyway.. if they don't need to offer this program to fill the rooms -- they won't.
So.. it's ill-advised to book a room in 'hopes' of free dining.. cause Disney will see that as an occupied room...
WAIT to book your free dining reservation til once the offer is out.. usually early April.
Save Up to 30% on Rooms at Walt Disney World!
Save up to 30% on rooms at select Disney Resorts Collection hotels when you stay 5 consecutive nights or longer in late summer and early fall. Plus, enjoy other savings for shorter stays.This offer is valid for stays most nights from August 1 to October 11, 2025.
CLICK HERE