How it works is that you get 1 snack, 1 table service (sit down with a waitress), and 1 quick service (fast food) meal per night of your stay. Our trip was for 8 nights/8 days so each of us had 8 snacks, 8 table service, and 8 quick service meals for the trip...which broke down into 2 meals a day plus a snack, which I used to get a muffin for breakfast each morning, so all our bases were covered.
My husband and I had never used the dining plan until this year because 1) it's a ton of food and we would spend less paying as-you-go, and 2) my husband hates schedules and being tied down by a ton of reservations.
However, we went in September of this year and they were offering free dining, so it would have been idiotic to turn down free food. We weren't so sure about how it would all work out, but we ended up LOVING it. We had park hoppers and I made only one reservation per day, so it was the best of both worlds because I got a little structure, we got to try a lot of sit-down restaurants we otherwise wouldn’t have paid to eat at, and he didn't feel "tied" to a specific park because of where our reservation was. I think the free dining really helped us sort through the intimidating number of restaurants within WDW because we had nothing to lose. If we had a great meal, awesome! We paid $0 for a fabulous, romantic $175 meal at California Grill and a great $98 meal at Le Cellier. And when we had crappy meals (*cough* Crystal Palace), we didn’t have to walk away feeling angry that we wasted our money.
We don’t stay at the upper-echelon resorts, so free dining (as opposed to a room discount) is the better deal for us. From now on we’re going to try and vacation at times when it’s offered (we’re doing it again in December). I have to say though, DO NOT stay at a value resort during free dining – I would go ahead and pony up for Riverside. EVERYONE stays at the value resorts during free dining – you should have seen the bus stops this past September. There would literally be 10-15 people in line for all the other resorts, and HUNDREDS lined up for the All-Star busses. Yes, we got a 8-night vacation with free dining and park hoppers for the insane bargain price of $1400…but we decided that after this vacation it was worth the extra money to upgrade to a moderate in order to avoid the masses.
All that being said, I don’t think I’d ever
PAY for the Disney dining plan. As long as it’s free, we’ll definitely use it and have a great time. But I would never purchase it because I couldn’t justify that amount of food or money. I know we’d feel compelled to overeat to make sure we got our money’s worth. But when the dining plan is free, I don’t feel pressured to force down dessert or order something other than water to drink.
Hope that helps!