Abandoned by his trust fund girlfriend on a leaky sailboat in Nassau Bahamas, a slacker schoolteacher attempts to grab life by the helm.
Tom Sutcliffe, middle-class drifter, thinks he's ready to settle down. But when his trust-fund girlfriend leaves him on a leaky sailboat in Nassau Bahamas, he’s forced to reconsider his plan. Bollocks to Alice! He’ll sail himself around the islands. When she’s found herself in the slums of Calcutta, she’ll come back to find a real man!
Reality check. Tom doesn't know a bilge pump from a bike pump. There’s one man who can help, boatyard alpha dog Jimmy Bones, but his lessons from the school of hard knocks involve Speedos with sneakers, an ohmmeter, drugs and guns. Tom stumbles blindly into the world of dockyard eccentrics, fraudster mechanics and expat dreamers - a rum-drenched world of “real men” that conspires against him and pins him to the dock.
The mast is creaking, the boat is leaking and Alice is never on Skype. Tom's sinking into an existential abyss. Enter a Bahamian temptress, a hurricane named Edna, and the struggle to leave the island capital becomes the ultimate rite of passage. From a thirty-year-old boy to a man.