Combine the wine, sugar, cinnamon, star anise, orange rind and 1 cup (250ml) water in a medium saucepan. Place over medium heat and cook, stirring, for 2 mins or until sugar dissolves. Add the pears and bring to a simmer. Reduce heat to low. Cover with a piece of baking paper to help keep the pears submerged in the poaching liquid. Cook for 45 mins or until the pears are tender. Use a slotted spoon to transfer the pears to a deep-sided dish.
Bring the poaching liquid to the boil in the saucepan over high heat. Cook, stirring occasionally, for 10 mins or until syrup reduces by half. Drizzle over pears and set aside to cool to room temperature. Place in the fridge for 2 hours to chill.
Meanwhile, to make the chocolate sauce, combine the chocolate, cream and sugar in a small saucepan over medium-low heat. Cook, stirring, for 2-3 mins or until chocolate melts and sauce is smooth. Set aside to cool slightly.
Serve the pears chilled or at room temperature. To serve, divide pears among serving plates. Drizzle with poaching liquid and chocolate sauce.