It takes place mostly if not entirely after Henry Morgan burned Panama City (1671)[1] and before the earthquake that destroyed Port Royal, Jamaica (1692).

When he is ten, Communism ends in Cuba, and his father (apparently a "wiseguy") moves there with him to run a casino.

Details he notices around that time make it clear that he is now centuries in the past, though Brother Ignacio is still in the monastery.

Then Chris's ship sails to Spain, where he becomes infatuated with Estrellita, the maid of a wealthy young married woman.

They capture a Spanish slave ship, and Burt puts Chris in charge of taking it to Port Royal.

Chris rejoins Burt, and their fleet engages in successful and unsuccessful piracy, sailing around South America.

Chris escapes and finds the dying Burt, who gives him his maps to the treasure he has buried on the Pearl Islands.

Finishing his manuscript on a plane to Miami, he explains that he plans to enter his childhood monastery as a lay brother named Ignacio, follow young Chris out of the monastery into 17th-century Cuba, go to Veracruz to meet him and take care of Novia, and eventually take his place as her husband and recover Burt's treasure.

"[7] At one point, in response to a prayer of repentance, Chris hears the voice of God as an audible sound.

Chris tells his story in an informal style reminiscent of Wolfe's Wizard Knight (narrated by another young American man), but slangier and more irreverent.

[14] Paul Di Filippo described Pirate Freedom as "remarkably straightforward for Gene Wolfe" and "rip-snorting".

He praised the minor characters and the accurate depiction of the period, adding that "Wolfe also makes sure to substitute hard reality in place of any cliché".

[3] Paul Witcover called the book "deceptively breezy" and "surprisingly dark", and said it dealt with deep Christian questions.