When the charming, yet undeniably reckless Sinbad finds himself cast out to see and cursed to be unable to spend more than one day and night on land following the death of his brother, he is ultimately delighted to discover a motley group of travelers with whom he joins in search of adventure and answers regarding his mysterious destiny.

Maggie (Melissa McCarthy), a single mother, moves into a new home in Brooklyn with her 12 year old son, Oliver (Jaeden Lieberher). Forced to work long hours, she has no choice but to leave Oliver in the care of their new neighbor, Vincent (Bill Murray), a retired curmudgeon with a desire for alcohol and gambling. An odd friendship soon blossoms between the improbable pair. Together with a pregnant stripper, named Daka (Naomi Watts), Vincent brings Oliver along on all the stops that make up his daily routine, the race track, a strip club, and the local dive bar. Vincent helps Oliver grow to become a man, while Oliver begins to see in Vincent something that no one else is able to A misunderstood man with a good heart.