After big-time Hemingway fan Jack Phelan falls into a coma following an accident, he somehow finds himself in Key West, Florida, rubbing shoulders with his longtime hero. The legendary author has been sent down by "the main man in the clouds" to find out if Jack has what it takes to write a book for him. And though Hemingway knows his decision may very well determine whether or not Jack comes out of his coma, he doesn't have a clue that the book is going to be about him.
During the next four days, Jack and Hem not only knock around Key West, but they also travel to more of the legendary author's old haunts. Together the two meet up with many of Hemingway's long-gone friends and have some rollicking good times. But it's not all fun and games. Hem and Jack both find themselves facing highly-emotional tests of strength as well.