Coat a 13 x 9-inch baking dish with cooking spray. Arrange 5 bread slices in bottom of dish in a single layer. Pour 1 cup wine over bread. Sprinkle with 1/8 teaspoon salt and 1/8 teaspoon pepper. Top with 3/4 cup cheese. Arrange the pear slices over cheese; top with remaining bread, wine, salt, pepper, and cheese.
Combine milk and eggs in a bowl; stir well with a whisk. Pour the milk mixture over the bread mixture. Let stand 20 minutes.
Preheat oven to 425°.
Cover strata and bake at 425° for 30 minutes. Uncover and bake an additional 25 minutes or until golden brown. Let stand 10 minutes.