Johnnie Crosswell, a Park Service maintenance worker on St. John and former Marine, yearns for adventure on the high seas. When an abandoned yacht sails into Hawksnest Bay, he places a low bid on it at public auction, if only to dream. His interest in creative writing leads to a chance meeting with Greta, the sweet new librarian. When Johnnie wins the auction, his new found confidence provides the courage to invite her on his ship's maiden voyage. Everything is going great until their perfect day at sea is completely ruined by his companion Stumpy, an unruly iguana. He decides the only way to redeem himself is to write an amazing seafaring tale to impress Greta. But first he must embark on a solo ocean adventure to visit old pirate towns and forts across the Caribbean. On the first stop of his journey, Johnnie discovers a stowaway. The fun-loving cruise ship activities director is hiding from the authorities. But they develop a friendship and Johnnie offers to help. Meanwhile, Johnnie's arch nemesis, Thomas Smith, spots him and renews his pledge of vengeance. As if things couldn't get stranger, modern day pirates attack their ship. To get away, their only recourse is to sail into a raging storm. Can Johnnie survive the onslaught of dangers long enough to face Greta and tell her his true feelings? Or will he choose a safer course?