Wah Do Dem (2010)

In WAH DO DEM, young Brooklyn musician Max (Sean Bones) decides to go on a Caribbean cruise alone when his girlfriend Willow (Norah Jones) dumps him cold two days before the trip. Once in Jamaica, Max quickly escapes the tourist zone for more "authentic" surroundings and in the process is robbed of his possessions and is stranded, and literally misses the boat. As Max sets out for the American Embassy in Kingston on foot, Jamaica is waiting to meet him with unexpected and extraordinary encounters, including a full-moon celebration with the legendary reggae group The Congos, and a dreamy stay with a Rasta prophet (Carl Bradshaw, THE HARDER THEY COME).

Source: TMDb