Put ice in the blender. Add the cooled grilled pineapple, the pineapple juice, sorbet and ice cream. Pulse until the mixture is smooth and creamy. Pour into 4 large wine glasses. Top each glass with a splash of club soda. Serve.
Heat grill to high. Brush pineapple with oil and grill until golden brown on all sides.
Recipe courtesy of Bobby Flay, 2008