Charlie leaves the winter in New England behind and heads to sunny Windermere, Florida. Charlie teams up with 2-time World Series Champ Johnny Damon. Johnny Damon hosts his 2-day charity event all to raise money for the Johnny Damon Foundation in which some proceeds go to the Wounded Warrior Project. Charlie critiques Johnny Damon’s golfing skills, as well as some of the other celebrities. Charlie is supposed to golf but decides to ditch the clubs for fishing poles. Johnny and Charlie get a golf lesson from trick golf shooter Dan Boever.