I'm headed to Disney World in 3 weeks with my In-laws, and they are paying for our trip as well. We have a total of 15 people, my mother and father in law, my 2 sisters in laws with their husbands and each have 2 kids, and my husband and my 3 kids.
I am so excited about this trip. Even just the planning has been fun. We got together to talk about things we want to do while we're there (emails work great if you can't physically get together.).
We have made reservations to do a few meals together, and we're staying in the same hotel, but other than that we're each on our own. I'm guessing my husband's parents will either enjoy some alone time without kids, or tag along with one of their kid's families for the day, not sure yet. But one great thing to take advantage of is the "Magical Gatherings" which are special meals or events for groups of 8 or more. We have scheduled the safari Dinner magical gathering, and I've heard great things about it. So I'm looking forward to that. Also the first night we are there, we are all meeting for a late dinner at 1900 Park Fare for a character meal with Cinderella.
Our trip is 4nights on land, 3 nights on sea. So then the cruise portion, we have dinners together each night, but the rest of the time we're on our own.
I don't see why it won't work out great.
A couple years ago, my parents took us all on a family vacation ot Maine. It worked the same way, we tried to meet for dinner, but then we were on our own during the day. My parents would usually tag along with one of their kids for part of the day.
I think when traveling with anygroup, rememeber to be flexible. The way I see it, everything at Disney is fun, so if we don't do one thing we wanted, it's only been replace by something else that is fun. But it would be smart to talk ahead of time, because traveling in groups can be difficult, and you don't want to spend a lot of time waiting on other people. Maybe plan to view parades or shows together, and split off until that set time.
Have a great trip!!