Preheat oven to 350 degrees F.
Tear the bread by hand into large, bite size pieces and spread out in a single layer on a sheet pan. Place the bread in the oven until it is dry and toasted, about 15 minutes. Remove the bread and place into a large mixing bowl. Mix in the pineapple chunks, cranberries, chestnuts, sage and thyme. Set aside. Cut the sausage into 1/4 inch rounds. In a large sauté pan over medium high heat, add the oil and brown the sausage. Once the sausage is browned, drain any excess fat from the pan and add the onions and celery to the sausage, allowing them to sweat, about 10 minutes. Add the garlic and cook for another 3 minutes. Add the sausage mixture to the bread. Pour the milk and stock over the bread and sausage mixture, stirring to incorporate. Fill each half of a pineapple with the stuffing mixture and bake at 350 degrees F for 30 to 40 minutes or until the top of the stuffing has nicely browned. Serve immediately.
This recipe was provided by a chef, restaurant or culinary professional. It has not been tested for home use.