This dessert is easy, flavorful, and gluten-free. The red wine is reduced to a delicious, lovely syrup flavored with vanilla, cinnamon sticks, and bay leaf, and a bit of mascarpone cream on top of each pear adds an extra touch of sweetness to each serving.
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*Note: If making ahead, hold the pears in the poaching liquid, removing the cinnamon sticks, vanilla bean, and bay leaf. Cool the liquid and pears below 70 degrees, then store in airtight container in the refrigerator for up to 3 days. Remove the pears from the liquid and bring to room temperature, then proceed with the rest of the directions to finish the dish.
In a double-boiler or a stainless steel bowl over a simmering water bath, combine the chocolate, port, and butter. Melt, stirring constantly. Add the cream and incorporate into the melted chocolate. Let cool to room temperature and use a squeeze bottle or spoon to drizzle.
Peel the pears in long strokes to avoid creating a choppy surface on the peeled pear. Cut the pear in half lengthwise. Use a melon baller or small scoop or spoon to scoop out the seeds and core. (You are creating a small "bowl" in the pear half that will later hold the mascarpone cream.)
In a large saucepan, bring the wine and an equal amount of cold water to a simmer. Split the vanilla bean lengthwise and add to the wine and water mixture. Add the cinnamon sticks, bay leaves, and sugar.
Add the pears to the liquid and simmer until tender but not too soft, about 20-35 minutes. Remove the pears from the liquid and cool.* Remove the cinnamon sticks, bay leaves, and vanilla bean from the wine mixture. Continue to simmer and reduce the liquid by ¾ (the liquid left should be a thickened syrupy consistency). Be sure not to over-reduce or burn the syrup.
Meanwhile, in a small bowl, combine the mascarpone, heavy cream, cinnamon, vanilla extract, and powdered sugar until smooth. Add the butter to the reduced sauce and stir until combined.
To serve, place a small dollop of the mascarpone cream on a dessert dish. Place a poached pear half on top of the dollop which acts as a "glue" to keep it from sliding on the plate. Then fill the "bowl" of the pear with a generous amount of mascarpone cream. Drizzle the pear with the red wine syrup and chocolate ganache, if using. Serve.