Hoops McCann je najstnik, ki izhaja iz družine košarkaških zvezdnikov, a sam ne blesti v tem športu. Ne želi nadaljevati družinske tradicije in bi rajši postal umetnik. Za sprejemni izpit pa mora napisati in ilustrirati ljubezensko zgodbo, kar ga zelo muči, saj še nikoli ni bil zaljubljen. Najboljši prijatelj George ga prepriča, da z njim odide na poletne počitnice v Nantucket, kjer bosta osvajala lepa dekleta . Obljubi mu, da bo tam zagotovo našel navdih za svoje delo. Nato se pojavi lepa Cassandra, ki ga popolnoma očara.
With a name like Hoops McCann, he's bound to get that basketball scholarship after high school, right? Wrong! What Hoops really wants to do is write and illustrate a love story. To help him find his way, his friend George invites Hoops to come with him and his sister to spend the summer on Nantucket. The friends Crazy Summer begins when they pickup Cassandra on the way--she's being chased by a motorcycle gang. From here on in, it only gets crazier. Once on the island, Hoops and George, along with George's island friends the Stork twins and Ack-Ack (son of a marine), must help Cassandra save her grandfather's house from the greedy Beckersted Family. Along the way, Hoops must find a way to write his cartoon love story - and maybe a real one of his own.