In 1-quart saucepan,combine the brown sugar, whipping cream, corn syrup, butter, and vanilla. Heat to boiling over medium heat, stirring occasionally; remove from heat and mix in the pineapple.
Toast waffles according to pkg directions.
To serve, place two Eggo Waffles on a plate on top of each other. Top with pineapple sauce followed by whipped cream and a cherry. Serves 4.