Peel the pears and, using a melon baller or paring knife, core from the bottom, leaving the stems intact. Combine the wine, 3 cups water, the sugar, dried cherries, cinnamon stick and cardamom in a saucepan. Bring to a boil over medium-high heat, stirring to dissolve the sugar. Reduce the heat to medium low and add the pears (add more water to submerge the pears, if necessary). Poach until tender, about 10 minutes. Remove from the heat; let the pears cool in the liquid. (To make a day ahead, transfer the pears and liquid to a container, cover and refrigerate.)
Preheat the oven to 400 degrees F. Mix the chocolate, walnuts, 1 tablespoon melted butter and a pinch each of sugar and salt 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, 20 to 25 minutes.
Lay out 1 sheet of phyllo, brush with melted butter and sprinkle with sugar. Repeat the layering 2 more times. Cut the dough in half crosswise. Spoon the remaining chocolate mixture in the center of each piece 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 with butter and sprinkle with sugar. Transfer the pouches to a baking sheet and bake until golden, 20 to 25 minutes. Serve with the cherry syrup.