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My first thoughts were either the Antelope or The Terror, but things didn’t really end well for either of those ships. Grendel’s Revenge has a decent ring to it though.
The Entropic Force
Boaty Mcboatface
The Good Ship Marmalade
“It’s Brittany Bitch”
So when other ships spot us on the water approaching them to be boarded, their guy in the crows nest has to shout “it’s Brittany bitch on the horizon!” to the rest of his crew. That’ll make me giggle because my name is Brittany and I’d arguably be the least threatening pirate ever
The Very Official And Totally Not A Pirate Ship That Is Five Billion Percent Trustworthy And Doesn’t Just Have A Really Long Name To Distract You While Your Ship Gets Boarded
Sea Cucumber
Unsinkable the third
The Raging Cajun.