Cut the eggplants in half along their length. Using a spoon or small knife, carve out the center of five of the eggplant halves, leaving at least a 1-inch “wall” on all sides. Place the five hollowed-out eggplants in a baking dish, cut-side facing up. Drizzle the tops with the olive oil and set aside.
Melt the butter in a large frying pan over high heat. Once melted, add the chopped onion, reduce the heat to medium, and cook for 10 minutes, or until golden brown. Add the garlic and cook for an additional 4 minutes, or until fragrant. Add the Italian sausage and, using a spoon or spatula to break it up into pieces, cook until browned and starting to become crispy.
While the sausage is cooking, cut the sixth eggplant half into ½-inch cubes. When the sausage is finished cooking, add the eggplant, stir, and cook for at least 5 minutes, or until the eggplant softens. Add the tomatoes, Italian seasoning, salt, and black pepper. Stir to combine and bring to a simmer, then remove from the heat.
Preheat the oven to 350ºF. Spoon an equal amount of the sausage filling into each eggplant boat. Sprinkle the top with additional Italian seasoning and bake at for 45 minutes, or until the thickest part of the eggplant is easily pierced with a fork.
Enjoy warm!