A recent high school graduate and aspiring cartoonist named Hoops heads to Nantucket for the summer with his friend George. Hoops, who has a fear of basketball despite his name, is hoping to find inspiration for an art school scholarship. Upon arriving on the island, the duo befriends a musician named Cassandra, who is trying to save her grandfather's home from being seized by a greedy real estate developer. The developer plans to turn the property into condos, threatening the local culture and lifestyle. As they become embroiled in local affairs, Hoops and his friends must deal with the antics of snobbish locals and the looming threat posed by the developer's spoiled son.

The group decides to help Cassandra by entering a boating competition organized by the wealthy family opposing them. They hope to win desperately-needed funds for Cassandra’s cause. Along the way, Hoops and his friends hatch increasingly outlandish schemes to sabotage their rivals and ensure victory, all while tackling personal obstacles. Meanwhile, Hoops struggles to overcome his own insecurities and fears of failure, both in life and love. As events unfold, friendships are tested and strengthened, with each character learning important life lessons through their madcap adventures on the island. Amidst the chaos, Hoops finds himself unexpectedly inspired by the camaraderie and creativity he experiences over one unforgettable summer.