Ahoy, Cailyn!
Thanks for sailing back to the Disney Parks Moms Panel with another great question!
Pirate Night is my favorite night on the high seas! Guests will be dressed in their pirate-y best ready to eat like scalawags and party like buccaneers! Even Mickey, Minnie and all their friends will be dressed in their best pirate garb, ready to join in on the celebration.
I'm happy to give you an idea of when Pirate Night might be during a five night voyage! During the 5-Night Halloween on the High Seas Baja Cruise from San Diego that sets sail later this year, Pirate Night is currently scheduled for the second night of the trip. Schedules are always subject to change, but this gives you an idea of when you might expect pirate night for future five night cruises. If my memory is correct, I believe you're setting sail next year! Once your embarkation date gets closer, I suggest giving the Disney Cruise Line agents a call at (800) 951-3532 to check which night Pirate Night is scheduled for your cruise!
Once you arrive onboard, you will find each evening's suggested dinner attire located on your Personal Navigator newsletter or
Disney Cruise Line Navigator app. I just know you and your family will be heading to dinner dressed to impress no matter what the night calls for!
Beth