Preheat the oven to 350F.

Drain the oranges and cherries through a fine-mesh strainer over a large bowl. Allow to drain until ready to combine with the dip.

Spread the shredded coconut on a sheet pan in an even layer. Toast in the oven for 7 minutes, tossing with a spatula occasionally so as not to burn.

While the coconut is toasting, cut the pineapple in half, leaving the stem leaves intact. Cut the "meat" of the pineapple into a checkered pattern and scoop out with an ice cream scoop. Remove the harder rind pieces and dice the remaining pineapple chunks into bite-sized pieces.

Combine the toasted coconut and fruit into a large bowl with the cool whip using a rubber spatula. Spoon what will fit into the halved pineapple. Reserve the leftover in a covered bowl in the refrigerator to replace as it is eaten.