Hi Alycia,
Dining at Walt Disney World is one of my favorite "activities," so I'm so glad you asked this question. My family of 5 has vacationed both on and off the
Disney dining plan, so I can give you my thoughts. When we're not on the dining plan, we're more conservative in our dining choices and spending habits. We choose more counter service options, share more meals, and skip extra snacks and desserts. We might do 1 character meal, but no more than that. Although this might save us a little bit of money, it also changes our overall vacation experience.
When we're on the dining plan, we like to do 1 table service dinner each day, with a couple of those being character meals. In fact, the whole family loves to help look through menus to choose new restaurants for our vacation. We've been able to sample some delicious and unique restaurants this way that we never would have tried if we weren't on the dining plan. We can usually stretch our snack credits and counter service meals so that we don't have to pay for a lot out-of-pocket, other than gratuities. I'm also a big coffee drinker, so the refillable mug is one of my favorite things. One of the things I like most about using the dining plan is that it's carefree since we already know how much we're spending on meals and most of our dining decisions have already been made.
From a cost perspective, we've done the math and there isn't much difference for our family between the two approaches. There are some restaurants that give you more bang for your buck, like character meals, so if you're doing two character meals it might be worth it on that basis alone.
I hope this has been helpful, but please let us know if you have any other questions.
Have a Disney day!
Beth