Windy City (1984)

As kids, Danny and his friends were great dreamers who called themselves The Rogues, always stuck together, and had high hopes and big plans for the future. They were inspired by heroic pirates from old movies like Errol Flynn's Captain Blood. They'd watch these films together and dream about becoming bold adventurers themselves one day. A few decades later, the Rogues are still together but they are now busy with their adult lives and hardships and it seems like only Danny, a struggling writer, and Sol, his somewhat well-off happy-go-lucky best friend, still like to goof around. Mickey now owns a busy nightclub, Pete is a TV reporter for a daily show, Marty is a small businessman,Eddy is a failed stockbroker facing jail time, and Bobby is a fully-committed family man. When Danny learns that his ex-girlfriend Emily, the one who got away, is getting married, he realizes that he still has feelings for her and Sol convinces him to think about contacting her again before it's too late. Unfortunately, Danny also learns that Sol is terminally ill with leukemia. As Danny nostalgically recollects how he met and started a relationship with Emily, he tries to convince the Rogues to help him make one of Sol's biggest dreams come true: to sail the ocean on a real classic wooden sailboat, just like in the movies.