Ahoy there Catherine, and welcome to planDisney!
Wow! It sounds like you are planning an incredible voyage with quite the crew. As far as I'm concerned, when it comes to a Walt Disney World vacation, the more mates and scalawags on board, the merrier.
With a party of your size, it might be difficult to move as one throughout your visit, but sitting down to enjoy meals together and meeting up to experience a few attractions as a group is a great idea. Consider, for example, taking a cruise on
Pirates of the Caribbean (one vessel may even be able to carry your entire group!) followed by lunch or dinner at
Jungle Navigation Co. LTD Skipper Canteen.
To make several
Advance Dining Reservations around the same time, you'll need to use multiple
My Disney Experience accounts. I recommend splitting up into 3 or 4 smaller crews, and when you check-in at each restaurant, let the Cast Member know that you would prefer to be seated in the same area.
Here's how to make this work. Let's say Jack Sparrow, Elizabeth Swann, and Will Turner are three adults in the group of 19, and the whole crew wants to dine together at
Ale & Compass Restaurant at
Disney's Yacht Club Resort. Jack, Elizabeth, and Will should each attempt to make a reservation in their My Disney Experience account for 6-7 as close to the same time as possible. If a party of 6 or 7 is too large, they may need to have their friend James Norrington assist as well, and each reserve a table of 4 or 5.
I hope everything works out, Catherine, and that you arrrr able to sit and relax together on your visit. Even if you can't reserve all of your preferred meals and times on your first try, I suggest checking back periodically as your trip approaches to try and catch an opening. Thanks for stopping by planDisney en route to your adventure, and if there is anything else we can do before you set sail, come see us again.
Betsy