Traveling with a large group of different ages

You've already said it, but I would go in with the expectation that you don't need to stay together the whole time. That way everyone gets what they want out of the trip but you can still meet up for family dinners, etc. Let me know how it goes, especially with the 18 month old! We're going down in December with MIL, FIL, BIL, myself, DH, and our daughter (Penelope like yours if I remember correctly!) who will be 27 months at the time so I'd love to hear some first hand tips when you get back!

So cute! I start tearing up whenever I think about our Penny's first trip too! She's a HUGE princess fan and also loves Mickey, Minnie, and the Pooh characters so I hope she just loves it. Doesn't Baymax do meet and greets in the Animation building at Hollywood Studios? Or is he not there anymore?

My DH, myself and my daughter (9) went last year with his sister, husband and 3 kids (5,3 and 1).

My daughter is older and able to handle a little more running around, so my SIL and family usually met us in the morning and we did a few things together and then went our separate ways for the afternoon and evening. We had breakfast together a few times because that was usually the calmest meal of the day for all of us. We also attended the Halloween party together and that was a lot of fun!

Overall, it was a great trip because everyone knew that we could not possibly be together all the time. We spent a decent amount together as a group outside the parks (in the pool, in DTD), but once in the parks we would do our own things since my daughter was able to go more of the thrill rides and did not want to do things like meet Sofia the First. It also meant that they did not have to feel like they had to run their smaller kids crazy trying to keep up. Nothing is worse than an overtired toddler faced with Magic Kingdom stimuli. Separating gave them and their kids the chance to move at their own pace.

So, overall tips would be to make definite plans you want to do together (like you already have), plan some downtime together at the resorts, meet for meals, meet for some of the shows, and most of all, have fun!

I fully expect lots of pictures of Penny and her parents! This is going to be precious. Anyone taking a video?

Zz.