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1
Peel the pears and core from the bottom, leaving the stems intact.
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2
Combine the wine, 3 cups water, sugar, dried cherries, and cinnamon stick in a saucepan. Bring to a boil over medium-high heat, stirring to dissolve the sugar. Reduce heat to medium-low and add the pears. If necessary, add more water to submerge the pears. Poach until tender (approx 10 minutes).
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3
Remove from the heat and let the pears cool in the liquid. To make a day ahead, you may transfer the pears in the liquid to a container, cover and refrigerate.
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4
Preheat oven to 400oF. Mix the chocolate, walnuts (if using), 1 tbsp melted butter and a pinch of each salt and sugar in a bowl. Remove the pears from the liquid and stuff with some of the chocolate mixture. Simmer the poaching liquid over medium-high heat until syrupy (approx 25 minutes).
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5
Lay out 1 sheet of phyllo dough and brush with melted butter and sprinkle with sugar. Repeat the layering 2 more times, rotating slightly the next sheet of dough relative to the previous one. Cut the dough in half crosswise.
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6
Spoon the remaining chocolate mixture in the centre of each piece of phyllo and top with the pears, stem-side up. Pull up the corners of the phyllo to meet at the pear stem. Pinch and twist the excess phyllo. Brush the outside with butter and sprinkle with sugar.
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7
Transfer the pear pouches to a baking sheet and bake until golden (approx 20 to 25 minutes). Serve with the cherry syrup.
