@NWO-Azcrack Love this post!
My crew and I tend to try to shoot ourselves into weird places, or through certain gaps in the rocks or islands, or shoot past landmarks and try to swipe them with the sword or shoot certain targets while flying through the air (My brother sniped a passing sloop's lower bell while being launched out of the cannon and we heard a satisfying DING as it passed. The other sloop turned around and both crew members applauded/cheered as we went our separate ways.)
During the Gilded voyage over the holidays, I dressed my pirate in all red, gave him long white hair and a long white beard, big black belt, boots, and gloves, and outfitted the sloop in all red and green to look like a sleigh. Then I went around playing various holiday music through my speaking trumpet. I would gift people piles of chests, skulls, cursed cannonballs, or Athena Voyages and have a merry time on the seas. Most of the time I was met with cheer, a few times I was met with a blunderbuss, but it was all in good fun!
I have also done this with the Mercenary Voyages with all of the partially dug up chests that I scavenged.
