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Jolly Roger Reads

Books About Pirates, Swashbucklers, and other Assorted Buccaneers

Avast, matey! Here be several sea-faring tales of sunken ships, hidden treasures, bloodthirsty corsairs, and a whole heap of scurvy! Everyone likes a good adventure yarn, and pirates, both real and fictional, have had some of the greatest adventures in storytelling. Who hasn’t dreamed of discovering secret chests of gold or tasting the salty sea air as you sail about the tropics? So if you’re a fan of Black Sails, the Pirates of the Caribbean franchise, or just really love Talk Like a Pirate Day (September 19), these five books should help keep your piracy obsession afloat this summer.

Under the Black Flag: The Romance and the Reality of Life Among the Pirates by David Cordingly
A definitive and authoritative account of the Golden Age of piracy - the early to mid-eighteenth century - in the Americas and the Caribbean, Cordingly’s comprehensive text is drawn from original documents and records of the day. Everything is covered, from female pirates to types of ships to the legends of the high seas. The most interesting sections are those where Cordingly explores and exposes certain myths we have come to believe about piracy (i.e. “walking the plank” is pure fiction!) and those where he analyzes the books, movies, plays, and media that have influenced our romantic conception of pirates. Some of these sections can be quite brutal, such as the detailing of what happened to captives, how pirates were punished if caught by the crown, and the difficulties of life aboard ship, but if you want a historical basis for the world in which pirates operated, this is the book for you.

Treasure Island by Robert Louis Stevenson
No swashbuckling list would be complete without the most popular pirate story ever written. Treasure Island has been read by generations of both children and adults since it was first serialized in 1881. The tale follows young Jim Hawkins, who finds himself in possession of a secret map leading to Treasure Island, where a massive horde of pirate booty is rumored to be stashed. The gallery of characters involved in Jim’s quest include the good-hearted and the obtuse as well as the frightening, the mad, and the dirty-crossing. Not to mention the affable and ambiguous Long John Silver who is at points friendly and humorous and at others dangerous and menacing. Though it is perhaps the simplest and greatest of adventure novels in terms of plot, it’s the surprisingly complex character relationships that transform this story from a straightforward epic into one of friendship, loyalty, coming of age, courage and honor, and the uncertain meanings behind "good" and "evil."

The Princess Bride by William Goldman
Fencing. Fighting. True Love. Strong Hate. Harsh Revenge. Giants and beasties and pirates and rogues. Captures and escapes. Truth, lies, death, and miracles. You’ll find it all in William Goldman’s contemporary classic. The film adaptation seems to be the version that most people are familiar with nowadays; but even if you adore the movie, I promise you that the book will surprise you. I myself was one of those people who grew up watching the movie time and again and wasn’t sure I needed the book to enrich the story, but now I have a deep and abiding love for both. There are discrepancies and differences, to be sure, but these are minor details for the most part. The core story is still what draws you in: the love between Princess Buttercup and farm boy Westley and all the obstacles in their path, including treks into piracy and magical mayhem. Driven along by master dialogue and witty writing, this book is truly a modern fairy tale and an excellent choice for those who like their pirate stories on the swooning, romantic side of things.

On Stranger Tides by Tim Powers
Puppeteer John Chandagnac is sailing toward Jamaica to claim his stolen birthright from an unscrupulous uncle when the vessel is captured by pirates. Offered a choice to join their seafaring band or die, Chandagnac assumes the name John Shandy and a new life as a brigand. But more than swashbuckling sea battles and fabulous plunder await the novice buccaneer on the roiling Caribbean waters – for treachery and powerful sorcery are coins of the realm in this dark new world. Shandy will set sail on strange tides, following the savage, ghost-infested pirate king, Blackbeard, to the cursed banks of the fabled Fountain of Youth. Notable for being the basis of the title and the general plot of the fourth Pirates of the Caribbean film, Tim Powers’ novel is high adventure at its best, full of ghost ships, voodoo, and talking fungi. An excellent beach read if you’re getting away to sandy shores this summer - just don’t blame me if there’s no treasure on that beach.

We Are Pirates by Daniel Handler
A boat has gone missing. Goods have been stolen. There is blood in the water. It is the twenty-first century and a crew of pirates is terrorizing the San Francisco Bay. Phil, a struggling radio producer, wants to be a rebel and a fortune hunter. Gwen, his daughter, wants to be an adventurer and an outlaw. So when Phil heads for the open road, attending a conference to seal a deal, Gwen teams up with a new, fierce friend and some restless souls and they take to the open sea, stealing a boat to hunt for treasure. Daniel Handler’s (aka Lemony Snicket) novel is one of freedom, quests, and the deep search for happiness we all embark upon. Though it can be grim and bleak at times, ultimately it is a story about hope and always keeping a healthy dose of adventure in our lives.