Preheat oven to 400 degrees F.
Place prepared squash, apple, onions, and garlic cloves on a large baking sheet. Drizzle with oil and season with 1/2 teaspoon of salt and 1/4 teaspoon of pepper. Use your hands to rub the oil around so it covers all the vegetables and apple.
Roast in a preheated oven for 40-55 minutes, or until the squash is fork tender.
Once roasted completely, let the vegetables and apple cool enough to handle them, then remove the flesh of the squash from the skins and any of the remaining onion or garlic peels.
Add the roasted vegetables and apple to a blender and blend until smooth. Add chicken broth and blend again until smooth, blending in two batches if needed.
Return to the pot and stir in the coconut milk, half and half, butter, nutmeg, cinnamon, curry powder, 1 teaspoon of salt, 1/4 teaspoon of pepper, and the cayenne pepper. Heat and stir over medium heat until warmed through and the butter has melted.
Remove from the heat, then spoon into bowls and garnish with additional olive oil, Parmesan cheese, sour cream, bacon bits, and fresh chopped cilantro. Enjoy!