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Peel the pears but try to keep the stem on. Place the pears in an oven-safe dish and sprinkle with the sugar. Pour the red wine, vanilla, and water over the pears and place the lid on the dish.
Once your oven is down to about 350° F, place the pears in and close the insulated door. After about 3 hours remove the pears and let them cool a bit. Place the pears on a plate and pour the leftover juice into a sauce pan to reduce.
Serve the pears warm with a scoop of vanilla ice cream and drizzle with wine reduction.