On a drizzly, blustery day in January of 1942, four young Mello brothers, from Woburn, Massachusetts, hop aboard a Boston & Maine Budd Liner and head into Boston for one last fling before shipping off to fight in the Second World War. Their first stop is a small raucous bar in Scollay Square called the Red Hat, where they encounter three others also celebrating before two of them, brothers named Jack and Joe Kennedy, go off to war. Jack Kennedy links up with one of the Mello brothers, Danny, and the two young men from opposite ends of the social and economic scales begin what would become an unforgettable bar-hopping journey. Along the way, forging a unique, instant friendship, Danny and Jack reveal their deepest secrets and end up imparting some valuable lessons about life, including possibly the starkest of all. No matter how hard you try to control the direction of your life, your journey's end may just be inexorably foreordained.