Preheat your oven to 400°F. Cut the butternut squash in half lengthwise, scoop out the seeds, and place cut-side up on a baking sheet. Drizzle with 1 tablespoon of olive oil, sprinkle with salt and pepper, and roast for 45-50 minutes until tender.
In a large pot, heat the remaining tablespoon of olive oil over medium heat. Add the chopped onion and sauté for about 5 minutes until translucent. Then add the minced garlic and cook for an additional minute.
Scoop the roasted butternut squash into the pot with the onions and garlic. Add the vegetable broth, ground cinnamon, and nutmeg. Bring to a simmer and cook for about 10 minutes.
Blend the soup until smooth and creamy using an immersion blender or a regular blender in batches.
Stir in the coconut milk (or heavy cream) and heat through. Adjust seasoning with additional salt and pepper if needed.