A pie with a crunchy macadamia-nut-and-sugar-cookie crust, a supple pineapple-orange filling, and a cloud of whipped cream dotted with candied macadamia nuts beautifully balances textures.
Preheat oven to 375 degrees. Pulse 3/4 cup macadamia nuts in a food processor until they resemble coarse crumbs; set aside in a small bowl. Pulse cookies in a food processor until they resemble coarse crumbs. Add cookie crumbs and melted butter to nuts; stir to combine. Press mixture into a 9-inch pie plate. Bake until golden, 8 to 10 minutes. Transfer to a wire rack; let cool completely.
Put pineapple juice, orange zest and juice, 1/2 cup sugar, cornstarch, salt, 1/4 teaspoon vanilla, and the chopped pineapple into a medium saucepan. Simmer, stirring occasionally, over medium heat until thick and transparent, 5 to 7 minutes. Let cool 5 minutes. Pour into crust. Refrigerate 1 hour (up to overnight).
Heat 1 cup sugar and 1/4 cup water in a small saucepan, stirring to dissolve sugar. Cook over medium heat until thickened and golden brown, about 5 minutes. Remove from heat. Stir in remaining 3/4 cup nuts. Spread nuts onto a baking sheet lined with parchment, and let cool completely. Coarsely chop.
Beat cream with remaining tablespoon sugar and 1/4 teaspoon vanilla until soft peaks form. Spread whipped cream over pie, and refrigerate 30 minutes. Serve sprinkled with candied nuts.