Preheat the oven to 425 degrees F (220 degrees C).
Combine bacon, sour cream, shredded Italian cheese blend, onion, garlic, olives, pepper, and salt in a bowl and stir to blend. Place squash halves in a baking dish and fill each with stuffing.
Bake in the preheated oven until golden brown on top, 30 to 40 minutes. Serve garnished with parsley and cherry tomatoes.