Pirate Freedom by Gene Wolfe
There aren't many pirate novels being published these days but this is a good one. Wolfe did a lot of research on pirates, sailing, and geography for this novel.
The plot is fairly straightforward but the set-up is strange. Chris, a boy raised a post-Castro monastery in Cuba goes into the outside world and finds himself in the late 17th century. He becomes a sailor, a captain, a cow killer, and finally a pirate.
The novel is in the form of a confession or memoir written by Chris in the early 20th century where he is a priest looking back at his youth. There is no explanation for the time-travel. It just happens.
If the book has a flaw it is that there are too many coincidences. Nearly everyone that Chris meets returns later. Also, for some reason, all women seem to want him. He has four or five women chasing after him at different points.
The novel is at its best when talking about sailing and actual pirate raids. Without giving a great deal of detail, Wolfe manages to invoke the feeling that he was actually there.
Unlike larger than life characters like Captain Blood, Chris is very human. He makes mistakes and admits them, often judging himself harder than an outsider would.
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