Make the custard: In a saucepan, warm the milk, vanilla bean and seeds over low heat. Whisk the egg yolks and sugar in a bowl; beat in the flour. Remove the vanilla bean and whisk the milk into the egg mixture. Pour back into the saucepan and whisk over medium heat until the cream is thick, about 8 minutes. Transfer the custard to a bowl; lay plastic wrap on the surface and cool in the refrigerator for about 3 hours. Transfer to a large pastry bag fitted with a wide round tip.
Prepare the millefoglie: Preheat the oven to 400 degrees F. Cut the puff pastry into eighteen 3-inch rounds using a cookie cutter or a paring knife. Place the rounds on parchment paper-lined baking sheets, prick with a fork and bake until golden, 10 to 15 minutes. Set aside to cool; leave the oven on.
Make the maraschino sauce: Combine the black cherries, pineapple juice and maraschino cherry juice in a small saucepan. Bring the liquid to a simmer over medium heat and cook until the cherries are softened, about 5 minutes. Carefully transfer the mixture to a blender or food processor and puree until smooth. Strain the puree and set aside to cool. Store any extra sauce in the refrigerator for up to 2 weeks.
Prepare the pineapple: Dust the pineapple slices with confectioners' sugar and place on a baking sheet. Bake until softened and lightly browned at the edges, about 30 minutes. Let cool.
Make the chantilly cream: Whip the cream, confectioners' sugar and vanilla in a bowl with a mixer until fluffy and stiff peaks form. Chill.
To assemble, place a pastry round on each of 6 serving plates. Pipe the custard over it and top with a slice of caramelized pineapple, followed by a pastry round and chantilly cream. Top with one more pastry round and drizzle with the sauce. Put a maraschino cherry on top.
Photograph by Yunhee Kim
From Food Network Star: The Official Insider's Guide to America's Hottest Food Show By Ian Jackman. Copyright (c) 2011 By Food Network. By arrangement with William Morris Cookbooks/HarperCollins Publishers.
Recipe courtesy Serena Palumbo for Food Network Magazine