Heat the oil in a large pot or Dutch oven over medium heat. Add the butternut squash and apples and cook for 5-7 minutes, stirring occasionally, until slightly softened.
Add the garlic and onions and cook for another 2-3 minutes, until fragrant.
Season with salt and pepper.
Pour in the vegetable broth and bring to a boil. Reduce heat and simmer for 20-25 minutes, or until the squash is tender.
Carefully transfer the soup to a blender (or use an immersion blender) and blend until smooth and creamy.
Return the soup to the pot and stir in the heavy cream (if using). Heat through.
Serve hot, garnished with crispy sage and apple chips (optional).