As children, the group of friends, known as The Rogues, were inspired by heroic pirates from classic films and dreamed of becoming bold adventurers themselves. Decades later, the friends are now adults, living separate lives, but still close. When Danny learns his ex-girlfriend is getting married, he realizes he still has feelings for her and convinces Sol, who is terminally ill, to help him make one last dream come true: sailing the ocean on a classic sailboat, just like in their childhood fantasies.
Windy City
A thirtysomething writer faces a crisis of identity, revisiting fond memories of his youth in Chicago as he attends his ailing friend's wedding to his former lover.