Hello, Annette! Welcome to planDisney. Thanks for sailing our way with your question!
I bet you will have the cutest grandkids on the high seas with your advanced planning and coordination efforts! I always get a kick out of seeing the adorable outfits onboard, and it sounds like the other cruisers are in for a treat.
Yes,
Very Merrytime sailings out of San Diego do include a Pirate Night. Depending upon the length of your sailing, there will also be an optional dress-up night. Dress-up means a suggested jacket for men and a pantsuit or dress for women. If you'd like to submit another question to me and share your sailing date, I can let you know which
dining attire is suggested for each evening. You may also
call an agent at Disney Cruise Line to inquire about your specific sailing and what they might have scheduled.
You will be able to view the entire activity schedule via the
Disney Cruise Line Navigator app after you have boarded your ship, so please be sure to download the app before your travels begin. As far as planning for outfits, I suggest that you plan a holiday outfit, a pirate outfit, a dressy outfit, and maybe even a pair of matching Christmas pajamas. Some guests love to take pictures with Santa Claus or with their favorite Disney Characters in their holiday jammies. I even saw some big family groups attending breakfast together in their pajamas on my last Very Merrytime cruise. They looked quite jolly!
I hope that this information helps you as you move forward with your planning. My pals and I are always hoping to get our fellow guests' plans in shipshape. Cruise back to us in the future if we can be of more assistance!
Have a very merry time!
Adrianna