As a general rule, if you have kids and/or can get it at a discount, it's worth it. Otherwise, it's generally not. To save money using the adult dining plan you generally have to get the most expensive items possible at each meal. To take full advantage of it, you also have to eat more food than most people otherwise would - dessert at lunch and dinner and a snack in-between (or a snack for breakfast).
IMHO, it's not worth the hassle or the pressure to maximize the "deal" you're getting (again- the exception being if you have kids or can get it at a discount).
I knew if this business was ever to get anywhere, if this business was ever to grow, it could never do it by having to answer to someone unsympathetic to its possibilities, by having to answer to someone with only one thought or interest, namely profits. For my idea of how to make profits has differed greatly from those who generally control businesses such as ours. I have blind faith in the policy that quality, tempered with good judgment and showmanship, will win against all odds.
it all depends on how you want to experience the parks. I think a regular dining plan can be a good deal as long as you are planing on maximizing the amount of full service restaurants you go to. If you only do quick service with a few full service it will hard to make it worthwhile. I personally like the plan for convenience however and piece of mind knowing that everything is already paid for and I wont have to worry about dropping money besides souvenirs any more.
Last year, when I went to WDW, I skipped the dinning plan because I couldn't get the math to work.
Between my girlfriend and myself, we instead budgeted $100 worth of food a day for both of us. Breakfast was the typical grab some coffee and pastry thing. We did sit down restaurants for both lunch and dinner, and we hit our budget most days. I think the most we went over was $30 one day. We also grabbed ice cream snacks and other things to cool us down throughout the day as well. We never ate desert at lunch because that's just too much food, but we pretty much always got desert for dinner. And we never ate quick service meals for lunch or dinner.
However, booking reservations when "free" dinning is available is a pain. Of course, we booked our trip one month in advance.
One trick to save money when going out to eat is to drink water instead of a beverage. And Disney likes to charge a fortune for a fountain drink. If we were tired, we might opt for ice teas. And last I checked, the dinning option doesn't cover alcohol anyway.
How much does the dinning option cost for two sit down meals and the equivalent of a breakfast snack this year? I can walk you through the math, and we can pull up menus for places you would like to eat at to see how much your daily meals will cost. I definitely didn't cut corners on the places I wanted to eat at nor my food selections.
Also, consider that when I booked my trip last year, I received the hotel discount because I didn't book a package. If you're doing a package versus booking the hotel separately, what's your nightly room rate? One way that Disney charges for the dinning plan is by increasing the cost of your room to cover their "free" dinning.
So some simple budget math:
breakfast: $15 for two people
lunch: $30 for two people
dinner: $50 for two people
snacks: about $10 a day at most
That's a little bit over a hundred a day, but that assumes you're eating meals at dinner that run over $20 a person plus tip. And your lunch meals are $10-12 a person. Also, we packed cliff bars, which worked as snacks and alternative breakfast when we couldn't find a place to grab a pastry, which is tough in WDW.
It pays to do your homework. Figure out your costs with a package, and without a package. Look into all the discounts. I have used the dining plan once. That was the only vacation that I have been on at Disney World, where I shared a room with someone. A special rate came up for Coronado Springs, and my roommate wanted to do the dining plan. So, I went along with her that one time. I, was already saving money just by having a roommate. We ate at some very nice places that I had not tried before on that trip. I also tried a lot of new counter service places. That trip was back in 2007.
Normally, I don't book any kind of Disney Package. I book room only, and ask for the AAA discount. I pay for my meals out of pocket, and it usually works out cheaper than buying a dining package. Normally I only eat two meals a day on vacation, and I always eat breakfast.
On my 2009 trip, free dining was available during our stay, but I opted out of that because I was traveling with 2 other people who basically just eat one big meal a day. They almost never eat breakfast. Also even though we spent 10 days in the parks, we did not spend 10 days in a Disney World resort, so the free dining would have only been available to us for 6 days. It worked out just fine, and I ate pretty well at mostly counter service restaurants on that trip. It also gave me the chance to try many places that I have never eaten at. We splurged our last night, and had dinner at Ohana.
There's lot of information available on the internet, and in the guidebooks. Also, you can call, and ask questions about things before actually making your plans. Disney World isn't cheap, so it pays to do the math.