Tim Madden awakens one morning to discover a fresh tattoo on his arm, his car covered in blood, his girlfriend in bed with the town sheriff, and a woman's severed head in his weed stash. Sensing a setup and in desperate need to clear his name, he begins an investigation that soon begins to expose a web of corruption in the small coastal community of Provincetown.

In 1983, yacht sailor Will Parker leads an American crew financed by millionaire Morgan Weld to defeat during the America's Cup race against an Australian crew. Determined to get the prize back, Will convinces Morgan to finance an experimental boat designed by his ex-girlfriend Kate's new beau, Joe Heisler. When the boat is completed, the Americans head to Australia to reclaim the cup.