It's summer 1974 on an island off the coast of Connecticut, and all Jack Smith wants is a vacation like he enjoyed in his youth: swimming, sailing, and no worries. But Jack finds his summer plans quickly spiraling out of control. His estranged wife follows him to the island, looking for money. The priest and constable are conspiring his ruin. And the local Lolita is intent upon seducing him. Jack suddenly has more problems than he can handle; and he deals with them the only way he knows how: with rum and romance, all leading to a calamitous Fourth of July.