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Set against the Monmouth Rebellion of 1685, Tim Dawkins finds his quiet life in Brixham torn away as his father, a tinker and gunsmith is arrested for selling a pistol to a nobleman who used it in the killing of an officer at the Battle of Sedgemoor. Tim escapes and is kept hid from the soldiers by the town tavern keeper until he learns that his father has been sentenced is to be transported as slave labor to the Caribbean. He then sets off to see his father one last time, and with the aid of a wagon driver who finds him along the road to Taunton Castle, makes his way to the docks of Bristol just in time to see his father taken on board the last vessel putting out. Tim sneaks aboard, and hides below to avoid being seen; but after falling asleep in the cargo hold he awakens hours later to find the ship has put out and he now an unintended stowaway.
Tim is soon discovered and sentenced by the harsh-tempered captain to the same fate as the jailed rebels. He is literally thrown into the brig, only to be with his father as he dies uttering “I won’t rest till I see you in safe hands”.
Just as life seems to be at an end for Tim, he is shaken by a cannon ball crashing through the hull as the ship engages in battle. Now sinking the captain surrenders and the ship is boarded by pirates; Tim is liberated and on emerging topside he comes face to face with his would be rescuer, Raphael Sabatini’s legendary mercenary-turned-physician-turned pirate, Peter Blood. As the English sailors take to the longboats Tim pleads with Peter to take him with them instead; Peter reluctantly agrees and places him in the care of the two men who found him in the brig, the gentle giant Ben Croft and scrawny Dandy; but once aboard The Arabella a fire rises inside Tim. He throws an iron bolt at the captain he blames for his father’s death, striking him in the eye and knocking him over the side of the longboat, almost drowning him.
Peter decides that it’s best for Tim to find a proper situation in a friendly port rather than keep him on board a pirate ship; but they soon learn from the Governor of Tortola, the pirate known as Black Henry, that Tim blinded the captain, and in seeking revenge has placed a bounty on his head so high as to turn any man honest. With no safe haven, Peter resignedly makes Tim part of the crew and brings him on his day to day voyage between “Perdition and Purgatory”, as the men without a country wait for the other side of the calendar, the day when James II will be dethroned. But for Peter the waiting is more than that as he harbors an aching heart for his lost love, spouting Shakespeare all the while.
Tim’s journeys with Peter take him on a tour of the Caribbean of the 17th century; from French boucaniers of Hispaniola, Dutchmen sailing from Curacao, Jewish arms merchants on Sint Eustatius and on to battling Spanish Conquistadors; and all whom he meets believe that Tim is really Peter’s son, including the man they find stranded on their private island, ‘Nuthin’ Atoll’: London’s most well-known black Shakespearean actor. Throughout this journey Tim comes into his own amongst the men of the crew, demonstrating resourcefulness and quick thinking, courage under fire, prowess with the pistol and of all things, a natural-born master of the sword second only to Peter. But neither his skills or bravery will be of any avail when he faces what will be the young man’s most frightening challenge: the affections of the Governor’s daughter. Hoping to ease his own aching heart, Peter enlists Tim’s friends in a plan to further the cause of love and reunite his young Romeo with a most willing Juliet.

Filled with historic references with a humorous blending of British slang and Shakespeare, “Prince of the Caribbean” is anything but a pirate story, but rather a boy’s coming of age under the guidance of an unlikely but colorful collection of foster fathers, each of whom is grabbing at the last shred of a life torn away from them, and first love.