A group of childhood friends, inspired by heroic pirates, have grown up and pursued different careers. However, when one of them learns his ex-girlfriend is getting married, he's reminded of his lingering feelings for her. As he tries to rekindle their romance, he also discovers his best friend is terminally ill and convinces the group to help fulfill his dying wish: to sail the ocean on a classic wooden sailboat.
Windy City
A thirtysomething writer, struggling with midlife crisis, reflects on the lives of his young Chicago friends as his dying friend and the wedding of his old flame stir up nostalgic emotions.