Ahoy, Paula!
Congratulations on your upcoming cruise on the gorgeous Disney Dream! It is a beautiful ship, with so much to see and do. I've sailed on the Dream more often than any of the other ships, so it has a special place in my heart!
While entertainment offerings such as
Pirate Night are always subject to change - on the most recent sailings of this itinerary, Pirate Night has indeed been on the evening the ship visits
Castaway Cay.
When booking Adult Dining, my husband and I usually opt for the last evening onboard. By then, our kids have made friends and feel comfortable in the
Youth Clubs, and we've typically rotated through all of the Main Dining venues. If you book your Remy dinner, and find out at embarkation (when you receive your dining rotation) that it doesn't work for you, you can meet with the Dining Team onboard to make changes. There will be a time and location listed in your Personal Navigator (a detailed daily schedule you'll receive) to make dining changes on the first afternoon.
I have two words about your evening at
Remy: CHEESE CART. When I tell you I have dreams about the cheese cart at Remy? True story. It's AMAZING!
I hope this helps with your planning! Please let us know if you have further questions before you sail.
Have a magical day! - Diane W.