One Lousy Pirate

Sailing Away From it All isn’t What it’s Cracked Up to Be

Have you ever dreamed of sailing away from it all? Running out the clock in a tropical paradise or dropping anchor off the coast of a deserted island somewhere in the Caribbean? You’re not alone. One Lousy Pirate is a toe dipped into the waters of that runaway Caribbean fantasy. Journey along to Barbados, Bequia, and the Tobago Cays in search of your sea legs. From a local reggae fish fry to the summit of La Soufriere, and across the sparkling azure waters of the southern Caribbean, One Lousy Pirate is a funny, vivid quest to discover if the Caribbean sailing fantasy is what it’s cracked up to be.

One Lousy Pirate is for anyone who ever dared to dream of an alternate lifestyle, but was too scared to pursue it. It’s for travelers and armchair adventurers, for the desk-bound and those stricken with wanderlust. Dreams are important, for without them we may never realize who we really are as a person.

Author’s Inspiration: One Lousy Pirate was the result of an impromptu trip to the Caribbean. That trip, an off-the-cuff response to the many times I was asked what I would do after my then-upcoming round-the-world cycling adventure. “Go live on a sailboat in the Caribbean,” I blurted out one day. And the more I continued using that line, the more I began to think it might be something worth trying.