DS - AKA "Scurvy Pete" - is all set because I made him a pirate costume for Halloween 2 years ago. I used a hand-me-down red&white striped shirt, cut up the neck, sleeves and bottom. An old pair of sweatpants cut raggedy at the bottom, a sash, tacked a stuffed parrot on his shoulder, a bandana on his head. He also has a sword, but I think it will stay home - there is a limit to how much I will try to cram in a suitcase.
DD - AKA One-eyed Rosie - will probably wear a gauzy white shirt and some capris, with a sash around her waist.
Me/ Cantankerous Kate - something similar to DD
DH- Captain Mal du Mer - ????
We pretty much live as pirate all the time on our own boat! LOL!
Bandanas make great pirate headgear and take little room in the suitcase.