Roast Squash & Garlic: Preheat oven to 400°F (200°C). Brush halved butternut squash with 1 tbsp olive oil, salt, and pepper. Place cut-side down on baking sheet with garlic cloves wrapped in foil. Roast 40-45 minutes until tender and caramelized.
Sauté Aromatics: In a Dutch oven over medium heat, warm remaining 1 tbsp olive oil. Sauté diced onion and chopped sage for 5-6 minutes until soft and fragrant.
Simmer: Scoop roasted squash flesh into the pot with roasted garlic, vegetable broth, maple syrup, and nutmeg. Simmer gently for 8-10 minutes.
Puree: Puree soup with an immersion blender until completely smooth and velvety.
Finish & Serve: Stir in coconut cream, season with salt and pepper to taste, and serve hot garnished with toasted pepitas, sage, and a cream swirl.