Swashbucklers of the 7 Skies is a swashbuckling RPG that is set in a fantasy world where players can adventure across islands that float in the sky.^[1]: 425 Swashbucklers of the 7 Skies was intended an homage to pulp swashbuckling stories, including a full chapter discussing the tropes of the genre.^[2]: 265 Swashbucklers took place in an entirely original setting, where sky pirates battle each other in ships that fly across the sky.^[2]: 265 Chad Underkoffler used his PDQ system for this game, which has some similar characteristics to Fate – including its Fortes (or qualities) to be applied as freeform occupations, motivations, histories or organizations.^[1]: 425 Swashbucklers used a new variant of the PDQ system which Underkoffler renamed PDQ#; Underkoffler revamped his system mechanics for the first time, as PDQ# gave foibles and techniques to characters while its combat system made conflict more tactical.^[2]: 265 Swashbucklers had its own ship combat system to meet the needs of the setting.^[2]: 265

Chad Underkoffler had been designing a game about sky pirates as his first independent role-playing game for Atomic Sock Monkey Press, but put that game aside to develop Dead Inside (2004) instead.^{[2]: 261–262} Due to a business arrangement between Atomic Sock Monkey Press and Evil Hat Productions, Underkoffler was finally able to publish his game as Swashbucklers of the 7 Skies in 2009.^[2]: 265 The companies were able to make a joint arrangement to produce the game, despite a disagreement over the size; Fred Hicks from Evil Hat persuaded Underkoffler to use a 7" x 10" format, which was slightly smaller than the print size of a traditional role-playing game.^[2]: 265

Shannon Appelcline, in his 2011 book Designers & Dragons, noted that this was a more traditional RPG for Evil Hat, and commented: "Whereas The Zorcerer of Zo had received some criticism for its rough development of superb ideas, Swashbucklers of the 7 Skies was a more polished game, showing the benefits of indie designers working together in a larger design house."^[1]: 425 After its publication, Swashbucklers received a Silver ENnie,^[3] and was runner-up for the Indie Game of the Year.^[2]: 265