Ahoy, Margaret!
Welcome to the Disney Parks Moms Panel! I just love the
itinerary you have booked for the
Disney Dream with two magical days at Disney Castaway Cay! My family experienced the very first "double dip" cruise on the Disney Dream in 2011, and it was definitely one of my favorites. One day on this beautiful, tropical island is a treat, but two days is the cherry on top! Early June is also one of my favorite times to visit this Bahamian paradise.
In the past,
Pirate Night, including the spectacular Buccaneer Blast, has taken place on the second Castaway Cay day or Day Four of your vacation. This is always subject to change, and you'll have a better idea when your online check-in and booking window opens up. It will list which day the pirate festivities are planned.
As for your dining question, you can certainly request a particular
dining rotation for your sailing. You'll just need to call Disney Cruise Line at (800) 951-3532 to have your request noted on your cruise reservation. They cannot promise the rotation you request, but they will try to honor it if possible. I will say that all the dining venues on the Disney Dream are wonderful, and every meal is magical aboard Disney Cruise Line! You'll love getting to know your dining servers as they rotate with you each evening, and the culinary team is pretty amazing as well!
I'm so glad you stopped by with your cruise questions, Margaret! Please keep us posted as you continue to plan for your "double dip" on the fabulous Disney Dream.
Nancy