Stand pineapple upright and vertically cut a third from one side, leaving the leaves attached; set cut piece aside.
Using a paring or grapefruit knife, remove pineapple from large section in strips, leaving a 1/2-in. shell; discard core. Cut strips into bite-size chunks. Set aside 2 tablespoons juice from pineapple; invert shell onto paper towel to drain. Remove fruit from the small pineapple piece and cut into chunks; discard peel. Place shell in a large serving bowl or on a serving platter.
In a large bowl, combine pineapple chunks, strawberries, orange and banana. In a small bowl, beat cream cheese and reserved pineapple juice; spoon over fruit and stir gently. Spoon into pineapple boat.