Ahoy Katrina!
Wow! It sounds like you have a great crew ready to enjoy an amazing cruise onboard the Disney Dream! Since Disney Cruise Line offers something for everyone at every age, you have definitely chosen the best option for your vacation this summer!
You are correct about what to expect for your nightly attire on your three-night voyage. When my family has sailed in the past, I have dressed my son in nice shorts for dinner so it is acceptable for any of the little sailors in your group.
Mickey's Pirates IN the Caribbean Night is a fun-filled festive evening that includes a Caribbean-themed dinner in the main dining rooms, a high-energy deck party, pirate games, and an amazing firework show that will make the night sky sparkle! Your favorite Disney characters and many crewmembers will be dressed from head to toe in their pirate gear, and Guest participation is also encouraged. Many cruisers bring along their pirate attire from home while others purchase costumes, t-shirts, and accessories from Mickey's Mainsail on Deck Three. Pirate Night is one of my favorite activities offered onboard Disney Cruise Line, and I have many pictures in my home to prove it! I'm sure your crew will have a swashbuckling good time as well!
I hope my answers are helpful, Katrina! Thanks so much for visiting the Moms Panel!
Nancy