Hi Haley,
Welcome to the Disney Parks Moms Panel! Thank you for bringing this excellent question to us!
If you dine together, remember that parties of six or more are automatically charged a gratuity. If you book separately, you take your chances that cast members will seat your party separately. When we have traveled with a group, we have eaten together. We decided that family time was most important. My experience has been that we had fantastic service so we have always been happy to pay the gratuity.
Depending on the size of your party, however, you may have trouble securing reservations. On one trip, I was unable to secure a dining reservation for
Be Our Guest Restaurant at dinner. Even though I was online making reservations as early as possible, the system only had reservations available for 9:00 p.m. I called the dining reservation line and was able to make two separate 7:00 p.m. reservations for a party of three and a party of four. When we arrived at the restaurant, we told them we were together and they seated us together. Cast members always try their best to make each guest's dining experience fabulous.
In short, I suggest that you try to make the reservation for your entire party but be prepared to split the party if you need to do so to secure a better dining time. Having said that, traveling with large groups can test even the best of us. It is certainly acceptable to plan separate dining experiences during your trip!
I do hope you have a magical time!
-Donyell