Pirates! (Patreon)

My good friend is getting married in a few weeks and has asked me to throw him a casual one-shot for his bachelor party. We've settled on pirates as the theme, since the session is basically a complex drinking game, he is a big fan of One Piece, and it seems like a perfectly chaotic theme for one day of D&D.

The only thing that is set in stone is that the bachelor will be the invincible, and the other players his expendable first mates. My plan is to lay a map before them dotted with scattered islands, tell them "your goal is to ______" and let them island-hop until they have successfully ______!

I'll be running what I call "5e Lite" where character sheets are simplified and everyone's abilities are on cards. This makes opening a treasure chest a lot of fun, since everyone gets a bunch of new cards! It will also be the main method of progression so, whereas a character might start with a pistol and sword, they will end up with a Staff of Seagulls, Hook of Hurling, Eyepatch of Scrying, and such items. By the end, they should be able to _______ with relative ease!

Of course, I want the whole voyage to be as kooky and dramatic and memorable as possible. 

SO, the reason I'm writing this is to humbly ask you for your best concepts for magic items, sea and land encounters, enemy ship concepts, island oddities, and anything else you can think up which would be fun to interact with. Oh, and that all-important _______! Whatever should that be?

As thanks, I will be sharing all the hastily-made maps here afterward, so let's brainstorm some crazy ideas and make this a night to remember!