Ahoy, Elizabeth!
It is so great to hEAR from you again and to be able to assist you with your plans for your "Dream"y double dip cruise in June! My family sailed on the very first double dip back in 2011, and we loved having the opportunity to spend two days on
Disney Castaway Cay! The first day we enjoyed relaxing on the beach and swimming and then headed back to the ship a little early to experience the
AquaDuck without much of a wait. The second day my husband and I participated in the Castaway Cay 5K, enjoyed a family bike ride to the observation tower and interacted with stingrays during
Castaway Ray's Stingray Adventure. Both days were practically perfect!
I think you are smart to plan ahead for your cruise attire because it will make the days leading up to your magical voyage a lot less stressful. I like to have it all written down, so I can make sure everything makes it into the suitcase and I always take the list with me to refer to it each day. Scheduling is always subject to change, but you can expect three cruise casual nights, one pirate-themed night and one optional dress-up night. Usually the optional dress-up night is scheduled for Day Two. I never tell my family that it is optional because I always take advantage of the ship's photographers that evening and get a nice family photo of us all dressed up! They typically don't mind since they can change immediately following dinner.
Good luck with your plans, Elizabeth. I hope you'll visit the Disney Parks Moms Panel again if you have more questions about your vacation on the
Disney Dream! Nancy