Hi Kandice,
Thank you for submitting your question to the Disney Parks Moms Panel! You made a great decision choosing the dining plan! You will see that once you have planned your meals everything else will be worry-free!
The Walt Disney World Resort operates more than 100 restaurants of which about 70 offer table service and about 26 are located inside the Disney Parks. In other words, you have a lot to choose from! The question is what are you in the mood for? The most popular restaurants right now are Cinderella's Royal Table and the Be Our Guest Restaurants located inside Magic Kingdom.
I would definitely recommend a character dining experience. I am sure that your family would enjoy it and with a little boy, I would recommend dining at Chef Mickey's located inside the Contemporary Resort, which features a buffet or 'Ohana located inside the Polynesian Resort, which is family styled dining offering an "all you care to eat" menu. Having two boys myself, it is a challenge to find a place they would like to eat that doesn't feature a princess. Recently, we experienced T-Rex, which is a restaurant located in Downtown Disney. My boys loved the dinosaur theme and the food!
Since the possibilities are endless, I am including the link to the main Disney Dining page so that you can search based on the location, dining experience and cuisine.
Bon Appetite!