Captain Lee returns to the Caribbean aboard My Seanna with a brand-new crew and one familiar face, Eddie Lucas, but a critical injury sends Lee to the hospital and puts the fate of the charter season in question. Eddie's return to yachting is rocky as he deals with a new team and a green but lovable deckhand. Chief Stewardess Francesca sets high standards for her interior crew, but this rubs some the wrong way.

Ready to let loose in the Caribbean, James instead finds himself disappointed on the first night out. Heads turn as My Seanna welcomes a new crew member, and Izzy makes a surprising decision, much to the chagrin of James. Francesca comes to grips with the ramifications of her emotional outburst. A charter group of thirsty 20-year-olds arrives, and Shane's mistakes push Eddie's patience to the edge.