Combine pears, wine, spices, and sugar in a medium pot over medium heat and bring to a simmer. Lower the heat and continue a gentle simmer until the pears are softened, about 20 minutes. Remove the pears and discard everything else. Cool to room temperature.

Soak the dried cherries in the rum for at least 20 minutes.

Preheat oven to 375˚F for high altitude (350˚F at sea level). Line a baking sheet with parchment paper.

Place one sheet of phyllo dough on the parchment paper Spray with cooking spray. Place a sheet of phyllo on top and lightly baste with butter. Continue layering the phyllo dough until all sheets have been used. Be sure to keep any sheets not being used covered with plastic or a towel.

Layer the pears down the center of the phyllo, and sprinkle with chopped chocolate and rum-soaked cherries. Gently fold the dough over the filling, baste with butter, and turn over and place the roll seam side down on the baking sheet. Pinch or fold ends under on either end. Baste the top with butter and sprinkle with turbinato sugar.

Bake for 15 - 20 minutes or until lightly browned.

Remove from oven and cool for five minutes before serving.