Two college friends, now in their thirties, admire each others’ lives and feel trapped in their own. Wes, tied to a demanding career and responsibilities to family, extends a work trip to drag his dispirited artist friend Luke to find Luke’s “one that got away.”

After trading in the seemingly charmed life of a gentleman for one of a swashbuckling buccaneer, Stede Bonnet becomes captain of the pirate ship Revenge. Struggling to earn the respect of his potentially mutinous crew, Stede’s fortunes change after a fateful run-in with the infamous Captain Blackbeard. Stede and crew attempt to get their ship together and survive life on the high seas.