To avoid an early eviction, Jack challenges Al to a race at the upcoming Citrus Cove Regatta: If Al wins, Jack will pay him the $1,000 rent and take his family home; if Jack wins, he keeps the money and earns the right to stay in the house for two more weeks rent-free. Al scoffs at the notion that Jack could defeat him in a race, but accepts the challenge. However, Jack hasn't sailed for many years and doesn't even have a boat. Scully, a local saloon keeper with a pirate's mentality whom the Chesters met earlier, befriends Jack and volunteers to help him on both counts.