Dan Kilmer is a former Marine sniper in his early thirties. He returned home from military service in the Middle East and gave college a try, but his combat experiences prevented him from fitting into campus life. In a South Florida boatyard, his uncle was attempting to refurbish an old cargo schooner, and Dan left college to help him finish the flagging project. After two years of work but before the 60-foot boat was relaunched, his uncle fell from a scaffold and died.

While still in his twenties, Dan inherited the schooner Rebel Yell. Soon after, he left the United States to embark on a series of voyages, mostly in pursuit of beautiful women and good times. While he was away from America, new federal taxes were imposed on luxury property, including privately owned yachts. Dan cannot pay these or other new taxes, so he can't return to the States without risking confiscation of his schooner. Instead he must always fly under official radar and earn a living by his wits while staying one step ahead of the IRS and other government agencies.

He must navigate the reefs of government control while always searching for a way to make money without the permission of the local authorities. This usually requires some type of shady dealing, subterfuge, and stealing from thieves as Dan moves from port to port. A shifting cast of crew members inhabits Rebel Yell, but the novel is about Dan Kilmer and his quest to live as a free man in an increasingly unfree world. In Castigo Cay, Dan must sneak back into South Florida under the radar to conduct a short-fuse rescue mission.