Heat the olive oil in a large Dutch oven or soup pot over medium heat. Add the onion, carrots, and celery, then cook for 5–7 minutes, stirring occasionally, until the vegetables begin to soften.

Add the minced garlic, thyme, sage, cinnamon, kosher salt, and black pepper. Cook for about 30 seconds, stirring constantly, just until the garlic and spices become fragrant.

Add the cubed butternut squash, sweet potato, chopped apple, and broth. Bring the mixture to a boil, watching the pot so the broth does not spill over.

Reduce the heat to low, cover the pot partially, and simmer for 25–35 minutes. The soup is ready for blending when the squash and sweet potato can be pierced very easily with a fork.

Blend the soup until smooth with an immersion blender, or carefully transfer it to a countertop blender in batches. If using a countertop blender, leave a small vent open for steam and cover the opening with a folded kitchen towel.

Stir in the coconut milk or heavy cream if using. Add the maple syrup only if the finished soup needs a little more sweetness, then taste and adjust the seasoning and consistency with additional salt, pepper, or broth.

Ladle the soup into warm bowls and finish with toasted pumpkin seeds, fresh thyme or chopped sage, and a drizzle of cream or coconut milk. Serve immediately with crusty bread.