When the Captain of H.M.S. Squeaky Jenny succumbs to influenza, Lamar De La Mar sees a chance to rise in the ranks as the spice trading ship's next Captain, but to do so, he'll have to seek the help of his horrible, but influential, girlfriend, the Princess Catherine.
Having accepted the Princess’s offer, Lamar De La Mar sets off on his first stint as Captain of H.M.S. Squeaky Jenny, but learns that leadership comes at a great cost.
After the wreck of H.M.S. Squeaky Jenny, Lamar and Dani-Boy find themselves stranded on a strange Island. As they try to figure out how to get back home, they realize that they’re not alone.
Lamar, Dani-Boy, and Rowe are swept into the fantastical world of Jakobar, where Lamar meets the girl of his dreams, Nola.
News of H.M.S. Squeaky Jenny’s wreck has finally reached the English shore. Distraught, Catherine takes Oceán on a road trip to her family’s estate in the country.
Caught between two worlds, Lamar is faced with a final decision. Will he stay on Jakobar at the cost of his mission, or sacrifice his happiness and return to his royal life?